Thiết Kế Bài Giảng Hóa Học 11 Nâng Cao Tập 2

"Thiết Kế Bài Giảng Hóa Học 11 Nâng Cao Tập 2 🔙 Quay lại trang tải sách pdf ebook Thiết Kế Bài Giảng Hóa Học 11 Nâng Cao Tập 2 Ebooks Nhóm Zalo ^S^E'' 1 • •-• k" ^^Rff ^^ f .. ^ 9AL. 1 = ^ - :•< : ^^^^n^ ^ . i& ^^^•Kll-l^-jiiS^ E'-" ^ :^ai. NHA XUAT BAN HA NOI TS. CAO CL/ GIAC (Chu bien) ThS. HO XUAN THUt -ThS. CAO THI VAN GIANG THIET KE BAI GIANG H O A HO C 1 1 NANG CAO TAP HAI 'X A NHA XUAT BAN HA NOi ChiAiNq VI HKmOCACBON KHONG NO BAI 39 ANKEN DANH PHAP, CAU TRUG, DONG PHAN A. MUC TIEU BAI HOC 1. Kien thCJfc HSbiet: • Khai niem, cong thiic chung cua day doiig dang anken, biit phSn loai va goi ten mot so anken defn gian. • ca'u true electron va ca'u triic khdng gian eiia anken. • ^ Viet dong phan ca'u tao va dong phan hinh hgc ciia anken. / HS hieu: • Vi sao ankeri co nhieu dong phan han ankan tucng iing. • Nguyen^ nhan mot sd anken co dong phari hinh hoc la do su phan bo' cac nhom the cf cac vi tri khac nhau ddi v6i mat phang ehiia lien ket n. 2. KT nang • Tilt cong thiic ca'u tao bie't -goi t6n va ngubc lai t& t6n goi viet dugc cong thiic call tao nhung anken dom gian, • Viet ddng phan hinh hoc va dong phan ca'u tao ciia anken. B. CHUAN B! CO A GV VA HS • GV: - May tinh, may chie'u, cac phie'u hoc tap. - Mo hinh phan til etilen, dong phan cis-trans ciia but-2-en. • HS: On tap kie'n thiic bai ankan va xem tru6c bai anken. C. TIEN TRINH DAY- HOC Hoat dong cua GV Hoat dong cua HS I- DONG DANG VA DANH PHAP Hogt dpng 1 1. Day dong ddng vd ten thong thudng cua anken GV chie'u mo hmh phan tit cua etilen len man hinh cho HS quan sat: a) b) yeu c5u HS thao luan vi cac va'n de sau: - Vie't CTCT cac cha't tie'p theo la dong dang cua C2H4. - Lap cdng thiic chung day ddng dang cua etilen. - Phan tich ca'u tao cua etilen tii do neu dinh nghia day dong dang cua etilen. GV yeu ciu HS neu each ggi ten thong thucfng cua cac ankan sau? CH3-CH2-CH3, CH3- CH2-CH2-CH3, CH3—CH—CH3, CH3 GV bo sung: - Ten thong thu5ng ciia mdt sd anken don gian la'y tii ten ankan tuong iing nhung doi dudi an thanh dudi Hen. HS quan sat va thao luan. - Cdng thiic phan tit ciia mot sd ddng dang cua etilen: C3H6, C4H8, C5H10... - Tii C2H4 theo khai niem ddng dang. QH4(CHA ^Q.kH4.k dat2+k = n thi-> C„H,„ (n>2) . - Etilen cau tao cd jndt lien ke't doi' (gdm mdt lien ke't CT ben vfing va mdt lien ke't 71 kem ben), vay: Anken Id hidrocacbon khong no mach hd trong phdn tit co mot lien kit dqi. HS ggi ten. CHi—CHo—CH-i propan CH3-CH2-CH2-CH3 butan CH3—CH—CH3 isobutan CH, - ci n them vi trf cua lien ke't d6i 6 trudc ten ggi. - Vi trf lien ke't ddi tren nguyen tii cacbon thii 1,2,... tuong iing ggi la a, p... GV yeu ciu HS ggi ten thdng thucmg cac anken CO cdng thiic sau: CH2= CH—CH3 GH2=CH—CH2—CH3 CH3-CH=CH-CH3 CH2=C — CH3 CH3 GV bd sung ten ggi cua mot sd gd'c cua anken: CH2=CH- gdc vinyl CH2=CH-CH2- gd'c anlyl HS ggi ten: CH2—CH—CH3 CH2=CH—CH2—CH3 GH3-CH=CH-CH3 CH2=C— CH3 CH, propilen a-butilen P-butilen isobutilen Hoqt dong 2 2. Ten thay the GV chie'u len man hinh ten ggi cua mdt sd anken don gian. HS quan sat va thao luan. CTCT CH2— CH2 CH2= CH—CH3 CH2=CH—CH2—CH3 CH3-CH=CH-CH3 CHj^C — CH3 ; CH3 T&n ggi eten propen but-1-en but-2-en 2-metylpropen Yeu cau HS nhan xet rut ra quy luat ggi ten cac anken theo ten thay the'. GV hudng din HS chgn mach chinh, Quy luat ggi ten: Sd chi vi tri nhanh - ten nhanh Ten chinh mach each danh sd rnach C. sd chi vi tri nguyen tit C diu tien chiia lien k^t ddi - en GV yeu ciu HS ggi ten cac anken sau theo ten thay the: CH2=CH-CH2-CH2-CH3 CH3- CH=CH-CH2-CH3 CH2=C —CH2—CH3 1 CH, - Mach chinh la mach chiia lien ke't ddi, dai nha't va cho nhieu nhanh nha't. - Danh sd C mach chinh bat diu tiit phfa gin lien ket doi hon. HS ggi ten: CH2=CH-CH2-CH2-CH3 pent-1-en CH3-CH=CH^CH2-CH3 pent-2-en CH2=CH -CH, CH, CH2=C - CH2-CH3 2-metylbut-l-en CH3 CH2=CH-qH-CH3 3-metylbut-l-en CH, 11. CAU TRUG VA DONG PHAN Hoqt dqng 3 / . Cdu trdc GV chie'u len man hinh cau true ciia etilen. a) b) GV yeu ciu HS thao luan cac vah de sau: - Trang thai lai hoa cua nguyen t i C. - Cau tao cua lien ket ddi. - Vi trf tuofng ddi cua cac nguydn tit. Goc lien ket HCC,HCH. HS quan sat. HS thao luln va tra Idi: - Nguyen t& cacbon ndi doi b trang thai lai hda sp^ (lai hoa tam giac). - Lien ke't doi gdm 1 lidn ket CT (ben viing) va 1 lien ke't 71 (kem ben). - Hai nguyen tit C va bdn nguyen tit H deu nam tren cjing rhgt mat phang. - Gdc lien ke't HCH va HCC gin bang nhau va bang 120° - Kha nang quay cua cac nguyen tur quanh true lien ke't d6i. - Hai nguyen tix C khong the quay tu do quanh true lien ke't C=C (do can trd bdi lien ket TI). GV yeu cau HS: - Neu khai nidm ddng phan. Hoqt dqng 4 2. Dong phdn > a) Dong phdn cdu tao HS thao luan va tra Idi: - Ddng phan la nhihig hgp chit - Dua theo cdng thiic cau tao thi anken dugc chia thanh nhung loai ddng phan nao? ' - Viet cac ddng phan ca'u tao va ggi ten anken cd cong thiic phan tir CsH^. khac nhau nhung cd ciing cong thiic phin tit. - Dua theo cdng thiic ciu tao dugc phan lam 2 nhdm: - Ddng phan mach C. - Ddng phan vi trf lien ket doi. HS viet ddng phan cua CjHigVa ggi ten: CH2^CH-CH2-CH2-CH3 pent-l-en' CH3-CH =CH-CH2-CH3 pent-2-en CH2=CH-CH-CH3 3-metylbut-l-en CH3 CH3 -CH2-(p=CH2 2-metylbut-l-en CH3 CH3 -CH =(p-CH3 2-metylbut-2-en CH, h) Dong phdn hinh hgc GV chie'u md hinh phan tii dpng phan cis ^trans cua but-2-en len than hinh. OH ^O 1. UPC cis-but-2-en HS quan sat va thao luan. H H •-106V '« ' . • I'C trsns-but-2-en GV neu vlti de: nhu vly but-2-en cd ddng phan cis va ddng phan trans vay di^u kien nao de cd ddng phan cis-trans? GV hudfng din, dieu khien HS giai quye't van de. -- Ca'u tnic ciia lien ket ddi C=C. - Ca'u triic khong gian cua lien ket doi C=C, su phan bd cua cac lien ke't don quanh C cd ndi doi. Yeu ciu HS riit ra dieu kien de cd ddng HS tham gia giai quyd't vlh de: - Lien ke't ddi gdm 1 lien ke't a va 1 lien ke't 7t. - Cac nguyen txx xung quanh lien ket ddi C=C nam trdn mdt mat phang nen khdng the quay dugc quanh true lien ke't. - Cd th^ neu so dd sau de giai thfch. phan cis-trans va khai niem ve ddng phan hinh hgc (cis- trans). R, R, C = C. R, R4 Viet ddng phan hinh hgc ciia pent-2-en. Dieu kien: Rl+R2 R3 + R4 + Dong phdn cis: khi mach chfnh nim ciing mot phfa ciia lien ket C= C. + Dong phdn trans: Khi mach chinh nam 6 phfa khac nhau cua lien ket C= C. HS vidt ddng phan hinh hgc pent-2-en. /QH5 U,Cs HsC^ H H / C = C \ C2H5 trans-pent-2-en 1. Cung co' bai: H '^ H c/5-pent-2-en Hoqt dqng 5 CON G CO BAI V A BAI TAP VE NH A GV khac sau mot sd kien thiic cho HS ve: 8 - Cong thiic chung cua anken. - Cau tao ciia lien^ke't doi. - Quy tac ggi ten anken. - Cac loai ddng phan cua anken. GV chie'u mot so bai tap sau len man hinh cho HS thao luln: 1. Ggi ten anken sau: CJH3 CH,— C — CH^-C = CH—CH, CH, QH5 A. 3-etyl-5,5-dimetylhex-2-en C. 3-etyl-5,5-dimetylhex-3-en 2. Cho 3 hidrocacbon sau: B. 2,2-dimetyl-5-etylhex-4-en D. 4-dimetyl-2,2-dimetylhex-4-en Ddp dn A. CH3 —CH2—C—CH2 CH, CH3 —CH2—C—CH—CH3 CH, CH3 —CH2—C—CH—CH3 QH5 (1) (2) (3) Hidrocacbon nao cho ddng phan cis-trans? A. 1, 2, 3 B. 2 C. 1,3 D. 2, 3 Ddp an B. 3. Trong phan tii cac anken, theo chieu tang so nguyen tit cacbon, phin tram khdi lugng ciia cacbon: A. Tang din B. Giam dan C. Khong ddi D. Bie'n ddi khong theo quy lull. Ddp dn C. 2. Bai tap ve nha 1, 2, 3, 4, 5 (SGK). D. HUdNG DAN GIAI BAI TAP SGK 1- a)S; b)S ; c) D; 2. Cong thiic phin tii C„H2„ (n > 2) Cong thiic cau tao chung: R'R^C=CR^R\ Diing bang sau de so sanh: Ankan d)D. Anken Xicloankan Thanh phin Cau tao Chiia C va H. - Mach hd. - Trong phan tit chi cd, lien ket don. Chiia C va H. - Mach hd. — Trong phan tix cd mdt lidn ket d6i C=C. Chiia C va H. - Mach vdng. - Trong phan tur chi cd lien ket don. 3. a) CH3 -CH2-CH=CH-CH3 b) CH3 -CH2-PCH2 CH3 c) CH3 -CH2-CH=C-CH3 CH3 d) CH2=([:-CH3 CH3 e) CH3 -CH2-CH2-p=CH-CH3 CH3 g) cH3-p(;:-CH3 CH3 CH3 4. a) Xiclobutan la ddng phan cua buten, thuoc loai ddng phan ciu tao (khac nhau ve ban chat nhdm chiic). b) Thf du fciing sd nguyen tit C la 4, G4H10 cd hai ddng phan nhu^g C4H8 cd ba ddng phan ciu tao, trong dd cd mot ddng phan ciu tao cd ddng phan hinh hgc: C4H,o: CH3-CH2-CH2-CH3 CH3-(pH-CH3 CH, 10 C4H8: CH3-CH=CH-CH3 CH3-CH2-CH=CH2 CH3 - C=CH2 I CH 3. H3Cs^ /H 3 H3C^ / H H ^ H H ^CH3 5. a) But-2-en cd ddng phan hinh hgc cis va trans con but-1-en thi khSng cd, do ciu tap cua but-2-en thoa man hai dieu kien: - Cd chiia lidn ket doi C=C. - Mdi nguyen tit C rnang lien ke't ddi dfnh vdi hai nhdm nguydn tur khac nhau. b) 6 penten ddng phan lai: A: CH3-CHi-CH=CH-CH3 CH3-CH2-CH2-CH=CH3 pent-2-en pent-l-en B: CH3 -CH2-(^=CH2 CH3 -(f:H-CH=CH2 CH3-(j:=CH-CH3 CH3 CH3 CH3 2-metylbut-l-en 3-metylbut-l-en 2-metylbut-2-en C: H3C^ /C2H, H3C^ / H . H ^ , H H^ ^C2H3 cz5-pent-2-en fra«5-pent-2-en Cac chat d day A (mach khong nhanh) va day B (mach cd nhanh) la ddng phan mach C ciia nhau. Hai chat trong day A cung nhu trong day B la ddrig phan vi tri nhdm chiic. Hai chat trong day C la ddng phan hinh hgc. 11 BAI 40 ANKEN TINH CHAT, DIEU CHE VA LfNG DUNG A. MUC TIEU BAI HOC 1. Kien thCfc HS bie't: • Quy luat bien ddi nhiet do ndng chay, nhiet do sdi ciia anken. • Tfnh chat hoa hgc dac tnmg ciia anken la phan iing c6ng, dieu che' va mot sd ling dung cua anken. • Cach phan biet ankan vdi anken bang phuong phap hoa hgc. HShieu: • Nguyen nhan gay ra phan iing cgng, phan ling trung hgp, phan iing oxi hoa khong hoan toan la do ciu tao cua phan tur anken cd lien ke't TI. • Co che' cgng axit vao anken, ndi dung quy tic Mac-c6p-nhi-c6p. 2. KT nang • Giai bai tap lien quan de'n anken. • Viet phuong trinh hoa hgc minh hoa tfnh chat hoa hgc cua anken. 3. Tinh cam, thai do Anken va san pham triing hop cd nhieu iing dung trong ddi sdng san xul't. Vi vay, giiip HS tlil'y dugc tim quari trgng cua viec nghien ciiu anken. B. CHUAN B! CUA GV VA HS • GV: - May tfnh, may chie'u, cac phieu hgc tap. - Hoa chat: Nudc brom, H2SO4 jj^, etanol, thudc tfm. - Dung cu: Ong nghiem, niit cao su cd gin dng dlji khf, kep dng nghiem, den edn, bg gia thf nghiern. • HS: On tap kien thiic bai ankan va xem trudc bai anken. 12 C. TIEN TRINH DAY- HOC Hoat dong cua GV Hoat ddng cua HS Hoqt dqng 1 Kiem tra bdi cu, GV chie'u hai bai tap len man hinh yeu ciu HS thao luln. 1. Neu dieu kien de cd ddng phan cis trans. Cho vf du minh hoa? HS 1: Diing sodd sau: R. C = R, ^ R, R4 2. Anken cd cong thiic CH3-9 =CH-CH2-CH3 CH3 Ten thay the' cua anken la: A. 3-metylpent-3-en B. 2-metylpent-2-en C. 2-metylpent-3-en D. 3-etylbut-2-en GV nhan xet ke't qua bai lam ciia 2 HS d^ cho HS khac nit kinh nghiem. Dieu kien: R, + Rj R3 + R4 + Ddng phan cis: Khi mach chfnh nim ciing mdt phfa cua lien ke't C= C. + Ddng phan trans: Khi mach chinh nam b phfa khac nhau cua Hen ket C= C. Vf du: H3C\ /CH3 H3C\ / H c=c c=c c/5-but-2-en trans-h\it-2-&n HS 2 chgn dap an diing. Dap an B. 13 I. TINH CHAT VAT Lf Hoqt dqng 2 /. Nhiet do sdi, nhiet do nong chay vd khdi luong rieng GV chie'u Jai bang 6.1 len man hinh cho HS quan sat, yeu cau HS nhan xet quy luat bie'n ddi cac tfnh chit sau cua anken: - Trang thai. - Nhiet do sdi. - Nhiet do ndng chay. - Khdi lugng rieng. HS thao luain lin lugt tra Idi cac cau hoi ciia GV, rut ra nhan xet: - Trang thai: + 3 anken dau la chat khf. + Cac anken khac la chit long hoac rSn. - t°nc, t^s va khdi lugng ridng tang theo chieu tang ciia phan tit khd'i. - Anken nhe hon nudc. 2. Tinh tan vd mdu sac GV yeu ciu HS nghien ciiu SGK va nhan xet vd tfnh tan va mau sac cua anken. HS nghien ciiu SGK va tra Idi: - Anken hoa tan tdt trong diu md, hlu nhu khong tan trong nudc. - Anken la nhirng chit khong mau. II. TINH CHAT HOA HOC Hoqt dqng 3 GV yeu c|u HS rut ra nhung nhan xet chung ve mdi quan he giiia dac diem ciu tao va tfnh chit ciia anken. HS dac diem cl'u tao cua anken: cd mdt lidn ke't doi (mot lien ke't a ben vung va mot lien ke't Tt kem ben). - Lien ke't doi du doan la trung tim phan ung. - Phan ung pha v&lien ke't % kem ben. GV yeu ciu HS: Cgng hidro HS thao luan. - Nhic lai khai niem phan iing cgng 14 - Phan ung cong la phan ling trong do phan tur hgp cha't hiiu co ket hop vdi phan tii khac tao thanh phan tii - Neu didu kien de xay ra phan iing c6ng H2 vao anken, vie't phuong trinh hoa hgc giua etilen va H2. - Vie't phuong trinh hoa hgc tong hap chat md'i. - Khi CO xiic tac Ni va dun nong. Phuang trinh hoa hoc: CH2 = CH2 + H2 —^ CH3-CH3 Phuong trinh hoa hgc tdng quit: quat anken cgng H2. C„n^'^ZH n + H2 -^C„H •n^^2n+2 - San phim phan ung cdng hidro vao anken la gi? (San phim thu dugc la ankan) GV lam thf nghiem : 2. Cgng halogen HS quan sat va thao luan. Din tiir tit khf etilen (tiir tiii dung khi) vao dung dich brom, yeu ciu HS quan sat giai thfch hien tugng bing phuong trinh hoa hgc. GV hirdng din HS giai thfch hien tugng. GV yeu ciu HS neu ung dung ciia phan ling anken vdi brom. GV hudng din HS nghien ciiu thf rtghieni hinh 6:3 trong SGK, yeu cau HS: - Rut ra ke't luln. - Vie't phuong trinh hoa hgc giQa - Tha'y dung dich brom (mau nau do) bi nhat din, chiing td ndng do Br2 giam. - Giai thfch: Do brorh tin cdng vao Jien ke't doi pha vo lien ke't n. - Phuong trinh hoa hgc. CH2=CH2 + Br2(dd) •CH2Br-CH2Br 1,2-dibrometan Ung dung: De phan biet anken vdi ankan do ankari kh6ng lam mat mau dung dich brom b dieu kien thudng. HS nghien ciiu SGK. - Kd^t luan etilen cdng clo tao thanh chat long dang diu, kh6ng tan trong nudc, ap suit trong dng nghiem giam lam cho nudc ding len. - Vie't phuong trinh hoa hgc. etilen vdi CI2. CH2=CH2 + C1 —^ CH2CI-CH2CI 1,2-dicloetan - Vie't phuong trinh tong quat giua - Phuong trinh tdng quit: 15 anken vdi halogen, san ph^m tao thanh la gi? C„H2„ + X2 ^ C„H2„X2 - San phim tao thanh la din xult dihalogen. 3. Cgng HX (X la OH, Cl, Br...) a) Cong axit GV ggi y de HS vie't phuong trinh hoa hgc cua anken vdi hidrohalogenua (HCl, HBr, HI), axit H2SO4 dam dac. GV chie'u so dd chung axit cgng vao anken len man hinh cho HS quan sat: \ = C + H-A I I H A HS vie't phuong trinh hoa hgc: CH2-CH2 + HBr -> CH3-CH2-Br etyl bromua CH2=CH2 + HC1 -^ CH3-CH2-CI etyl clorua CH2=CH2 + H2SO4 -^ CH3-CH2-OSO3H etyl hidrosunfat HS quan sat, phan tfch va tra Idi. /7^ I I V < + H^A-3^ -p^ (1) / V^'' I I H A Yeu ciu HS nhan xet ve: (2) - Phan ling xay ra qua bao nhieu giai doan. - Kieu phan cat phan tit H-A. - Do ben ciia cacbotion trung gian. - Phin tii nao tin cong vao ndi doi trudc. - Phan ling xay ra qua 2 giai doan. - Phan tur H-A bi phan cat ki^u di li. - Cacbocation la tieu phan trung gian kh6ng ben. - Phin mang dien tfch duong tin cdng trudc. b) Cgng nudc (phdn iing hidrat hod) GV ggi y HS viet phuong trinh hoa | HS: 6 dieu kien thich hop (cd H^ xiic tac va 16 hgc cua phan iing etilen c6ng nudc. dun ndng), anken cd the cgng nudc. CH,=CH,+H,0 ^^^CH3-CH2-OH etanol c) Hudng cua phdn iing cgng axit vd nUdc vdo anken GV vie't so dd phan iing cgng cua propen vdi HCl. 1-CH3—CH2—CH2—Cl HS quan sat, thao lUIn va tra Idi. CH,-CH=CH,+ 1- clopropan '-€H3-(J:H-CH 3 Cl 2- clopropan GV yeu ciu HS nhin xet san phim chfnh va san pham phu tiir do riit ra quy tac Mac-c6p-nhi-c6p. GV hudng din HS riit ra quy tac Mac-cop- nhi-c6p. GV yeu ciu HS vie't phuong trinh hoa hgc cua isobutilen vdi H2O. Phan ling giua propilen vdi HBr chp 2 san phim: 1- clopropan la san phim phu. 2- clopropan la san phim. chinh. Quy tac Mac-cop-nhi-cdp: Trong phdn iing vdi cgng HA hoac nudc vdo lien kit doi, nguyen tic H (hay phdn mang dien tich duong) uu tien cgng vdo nguyen tit C bdc thap hon (cacbon cd nhieu hidro hen), con A (phdn mang dien tich dm) Uu tien cgng vdo nguyen tii: C bqc cao hon (cacbon co it hidrO hon). HS vie't phuong trinh hoa hgc. CH3-PH-CH2-OH CH3-C=CH2+ H2e CH CH 3 san pham phu OH *• CH3—C—CH3 CH, san phSm chfnh GV chie'u len man hinh m6t bai tap trac nghiem nhu sau: Trudng hgp nao diing cho quy tac HS thao luln va chon. 2-TKBGHH11NCT2 17 Mac-cop-nhi-cdp. A. Anken bit dd'i xung c6ng vdi X2. B. Anken ddi xiing cgng vdi HX. C. Anken bit ddi xiing c6ng vdi HX. D. Anken ddi xiing cgng vdi X2. Dap an C. Hoqt dqng 4 4. Phdn dng trung hqp GV yeu ciu HS nghien ciiu SGK rdi tra Idi cac cau hdi sau: - Vie't phuong trinh phan iing triing hgp etilen. - Neu y nghia ciia cac dai lugng. - Tiir dd riit ra khai niem phan iing trung hop, each ggi ten. - Tuong tu yeu cau HS viet phuong trinh triing hgp cua propilen va but-2-en. HS nghien ciiu SGK va thao luan - Phuong trinh hoa hgc. n CH2 = CH2 ^ ^ (-CH2-CH2-)„ etileii polietilen - CH2 = CH2: ggi la monome. n: la he sd trung hgp (thudng liy gia tri trung binh). - Phan ling triing hgp la qua trinh c6ng hgp lien tiep nhidu phan tur nhd gid'ng nhau hoac tuong tu nhau tao thanh nhung phan tit rit ldn (ggi la polime). - Ten polime = poll + tdn monome. - Phuong trinh hoa hgc: nCH3-CH=CH2 -^^ (-(^H-CH^-)^ CH3 propilen nCH,-CH=CH-CH, 18 polipropilen ^ (-9H-9H-)„ CH3 CH3 polibutilen Hoqt dqng 5 5. Phdn dng oxi hod a) Phdn ifng oxi hod hoan todn GV lam thf nghiem ddt chay etilen trong khong khf yeu ciu HS nhan xet: - Mau nggn lia. - San phim tao thanh. -Viet phuong trinh phan iing chay cua etilen. - Viet phuong trinh hoa hgc chay tdng quit cua anken. -Til e n„^o va n™ HS quan sat thf nghiem va nhan xet. - Nggn lia khdng mau, sang xanh. - San ph^m khf, kh6ng miii. - Phuong trinh chay. 2C2H4 + 5O2 ^ 4CO2 + 4H2O C„H2„ + 3n02 > 2nC02 + 2nH20 Ti le n CO, 'H,0 = 1:1 b) Phdn icng oxi hod khong hodn todn GV lam thf nghiem: Sue khf etilen vao dung dich KMn04 (1) yeu ciu HS: - Neu hien tugng. - Giai thfch. - Ung dung cua phan iing. GV tuong tur yeu ciu HS vie't phuong trinh hoa hgc cua anken vdi dung dich KMn04. GV: Ggi y HS viet phuong trinh hoa hgc tdng quat. HS quan sat thi nghiem. Hien tuqng: Dung dich KMn04 mau tfm bi nhat din, cd ket tua nau den xult hien. Gidi thich: - Etilen phan iing vdi dung dich KMn04 lam cho ndng do KMn04 giam nen mau tfm nhat din, sinh ra Mn02 ke't tua mau nlu den. 3CH2=CH2 + 4H2O + 2KMn04 -^ 3CH2 - CH2 + 2Mn02-l + 2K0H I 2 I 2 2 OH OH - LSig dung de phin biet anken vdi ankan. HS vie't phuong trinh hoa hgc tdng quit. 3C„H2„ + 4H2O + 2KMn04 -^ 3C„H2„(OH)2 + 2Mn02i + 2K0H 19 DIEU CHE vA UNG DUNG Hoqt dqng 6 1. Dieu che + Trong phdng thf nghiem: GV gidi thieu: Etilen dugc dieu che' tur etanol theo phuong trinh hoa hgc: C2H5OH H2SO4 dac no°c > C2H4 + H2O Phuong phap dieu che' nay thudng lin cac khf nhu CO2, SOj. Vay dung each nao de loai bo SO2, CO2, tiit dd yeu cau HS trinh bay each lap rap bg diing cu dieu che' C2H4 sach. + Trong cdng nghiep: GV yeu ciu HS neu phuong phap dieu che' anken trong cong nghiep va HS thao luln. - SO2, CO2 la oxit axit nen diing mdt bazo manh nhu dung dich NaOH. - Hdn hgp khf trudc khi thu din qua binh dung dung dich NaOH. HS thao luan each lip dung cu dugc lap nhu hinh sau: HS trong cong nghiep anken dugc dieu che' ixt ankan bang phugng phap. - De hidro hoa ankan: vie't phucmg trinh hoa hgc minh hoa. Q H 2n + 2 1".P -> C H,„ + H 2n - Crackinh ankan ^ n H2n + 2 lO^.p > CpHjp+z + C„H2„ 2. lfng dung GV: Smi tip miu vat, tranh anh, m6t sd ung dung co ban ciia anken. Chieu 20 HS thao luan nhung iing dung chfnh ciia anken: len man hinh cho HS quan sat (hoac cho HS nghien ciiu SGK). Yeu ciu HS khai quit hoa iing dung cua anken, viet phuong trinh hoa hgc minh hoa (ne'u cd). Hoqt - Nguyen lieu cho tdng hgp hoa hgc. Vf du: axit hiiu co, keo din... Phuong trinh hoa hgc: 2CH2=CH2 + O2 Ag,t° -^ 2CH2 — CH2 - Tdng hgp polime. vf du nCH2=CH2 - ^ (-CH2-CH2-)„ -Lam dung mdi... dqng 7 CLING CO BAI - 1. Ciing cd bai GV nhac lai cac ndi dung pin nim vQng cho HS: - Tfnh chat vat If cua anken. - Phan ling cdng H2, X2, HA va quy tic cgng Mac-cdp-nhi-cop. - Phan ling triing hgp va oxi hoa. GV chie'u len man hinh cac bai tap sau de luygn tip. L Khi c6ng HBr Vao hdn hgp cac ddng phan mach hd C4H8 thi thu dugc tdi da bao nhieu san phim. A. 3 B. 4 C. 5 D. 6 2. De nhan bie't CH4 va C2H4 ta dung dung dich nao sau day: A. NaOH C. HCl B.KMn04 D.CUSO4 -BAITAPVENHA HS thao luan. Dap dn C. HS thao luan. Ddp dn B. 2. Bai tap ve nha 1, 2, 3, 4, 5, 6, 7, 8, 9,10 (SGK) 21 D. HU6NG DAN GIAI BAI TAP SGK 1- a)D ; b)D ; c) S; d) D. 2. Anken boat ddng hoa hgc hon ban ankan la do trong phan tit cd chiia lien ket T:, day la nhiing lien ke't kem ben nen cd kha nang phan iing de dang hon. Cac phuong trinh hoa hgc: a) CH3 - CH =CH2 + Br2 ^"' > CH3 -CHBr-CH2Br b) CH3-CH=CH2 + HI ^ CH3-CHI-CH3 c) CH3-CH=CH2 + H2SO4 (dac) -^ CH,-pi-CHj OSO3H H*,t° d) CH3-CH=CH2 + H2O -> CH,-CHOH-CH, e) 3CH3-CH

C„H2„ + 2 0,02 <-^iil ^ = o,02 22,4 Phuong trinh hoa hgc ciia phan iing vdi brom: C„H2„ + Br2 ^ C„H2„Br2 0,02 0,02 vay ta cd: (14n + 160) x 0,02 = 4,32 => n = 4. Cong thiic phan tur la C4Hg. Vi ankan thu duoc la mach nhanh, do dd CTCT cua olefin la: CH,=C-CH, CH3 (2-metylpropen) 22 A, : CH2=C-CH2-CH3 CH3 A2: CH3- C=CH-CH3 CH3 A3: CH3-CH-CH=CH2 CH, : 2-metylbut-l-en : 2-metylbut-2-en : 3-metylbut-l-en Al, A2 va A3 ciing mach C nhu nhau (khi hidro hoa ra cung mdt ankan), chi khac vi trf nhdm chiic (C=C). Chiing la ddng phan vi trf nhdm chu:c. 6. C„H2„+2 : a (mol); C„H2„: a(mol). - Sd mol Br2 = 0,1 (mol), Sd mol CO2 = 0,6 (mol) C„H2„ + Br2-> QH2„Br2 0,1 CnH2„+2 + 0,1 0,1 3n + l O2 — ^ nC02 + (n+l)H20 0,ln C„H2„+yO ,0,1 a) 0,ln + 0,ln = 0,6=^n = 3 -> nC02 + nHjO 0,ln CTCT ciia ankan la C3H8 (m = 44g/mol), CTCT : CH3-CH2-CH3; CTCT ciia ankan la C3H6 (m = 42g/mol), CTCT : CH2=CH-CH3. 0,1,4 4 + 0,1.4 2 , , , , ^ . 4 3 , , „ b)M,H= \ , ,4 . =4,3g/mol->d,,/, , =—=1,4 8 0,1 + 0,1 29 7. Sd mol Br2 = = 0,05 (mol) ' 160 QH2„ + Br2^C„H2„Br2 0,05 0,05 MA = 2,8 = 56 (g/mol) 0,05 vay CTPT ciia A la : C4H8 Cac cong thiic ciu tao: 14n = 56 n = 4. CH2=CH-CH2-CH3; CH2=C-CH3; CH3-CH=CH-CH3 CH, 23 Khi hidrat hoa A chi thu duoc mot ancol duy nhat. Vay CTCT cua A la: CH3-CH=CH-CH3 Cl'u tnic: H3CV CH3 C = C. H^ ^ H HsC^ / H / C = C H ^CHj 8. a) Ong nghiem thit nha't chuyen thanh dng nghiem b) b hinh 6.5. Hexan Khong phan iing vdi dung dich KMn04, khong tan trong dung dich KMn04 nen cha't long phin lam 2 ldp, dung dich khong nhat mau. Ong nghiem thii hai chuyen thanh dng nghiem c) b hinh 6.5. Hex-1-en cd phan ung oxi hoa vdi dung dich KMn04 lam nhat mau dung dich KMn04, san phim sinh ra khong tan trong nudc vi vay phan lam hai ldp. b) Phuong trinh hoa hgc: 3CH2-CH2-CH2-CH2-CH=CH2 + 2KMn04 + 4H20->3CH3-CH2-CH2-CH2-a^-aj[2 + 2Mn02+2KOH 9. Phuong trinh hoa hgc CH3—CH2—CH2—CH3 OH OH 500°C - CH2=CH-CH2^CH3 (I) H, Cong thiic ca'u tnic cua (II) ^CH3-CH=CH-CH3 (II) H,Cs CH, H3C\ C = C. y^ = C / ' \ H H - ^ H H ' ^CH3 c/.y-but-2-en rra«5-but-2-en 10. Vi etilen va propilen cd the tdng hgp ra polime va cac hoa chit hiiu co khac. Thf du: nCHz = CH2 I .p „ > (-CH2-CH2-)„ CH2=CH2 + CI2 -> CH2CI- CH2CI 500° C CH2 =CH2 + CI2 ^"^ " > CH2 =CHC1 + HCl nCH2 = CHCl '°:P ) r-CH2 - C H - ^ CI CH2 = CH2+ -O2 ->CH2-CH2 V (etilen oxi) 24 nCH2 = CH - CH, ':.•' > f-CH., -OU CH 3 A CH2=CH-CH3+Cl2 500° C > CH2=CH -CH2CI + HCl CH,=CH, + H,0 ^^^^^^ CH,-CH,OH E. TU LIEU THAM KHAO Su cd mat ciia lidn ket n trong phin tii anken lam cho anken cd kha nang phan iing cao hon nhieu so vdi ankan, trong dd phan iing cgng electrophin (ky hieu AEJ vao ndi ddi la phan iing dac trung nhat. Theo quan niem hien nay, hlu het mgi phan ung AE cua anken la nhimg phan iing nhieu giai doqn hay cgng tiCng bqc. O giai doan diu (chlm) tac nhan electrophin (mang dien duong) tin c6ngvao nguyen tit cacbon mang dien am (5~) cua ndi doi da bi phan cue hoa de tao ra cacbocation trung gian. Tiep theo, giai doan sau (nhanh) cacboncation se tac dung vdi phin rnarig didn Im cua phan tur tac nhin hoac dung moi de tao ra san phim cgng. Vi du: CH2=CH2 + HBr Qtam -Br^ CH,-CH2 l£i ^ CH3-CH2-Br Br CH2 = CH2 + Br2 "'•a > CH^ Br CH 2 „hLh > CH, CH, Br O • i ^ BrCH2-CH2Cl (46%) 25 Phan ling cgng cua mdt tie nhan bat ddi xung (nhu HCl, H2SO4, HOH, HBr, ICl,...) vao mdt anken bit ddi xiing (nhu CH3CH=CH2, CH3CH=CHCH2CH3,...) se uu tien xay ra theo hudng tao thanh cacbocation trung gian ben hon (quy tic Mac-cop-nhi-cdp). Vl du: „ Qr-GH3-CH-CH3 -BL ^ CH3-CHBr-CH3 (95%) (bin han) CH3CH=CH2 + HBr IS L O CH3-CH2-CS2 - ^ CH3-CH2-CH2-Br (5%) (kem ben) 16 BAI 41 ANKADIEN A. MUC TIEU BAI HOC 1. Kien thijrc HS bie't: • Khai niem ve ankadien va dac diem cl'u trtic cua he lien ke't doi lien hgp • Tfnh chit, phuong phap dieu che' va ung dung cua buta-l,3-dien va isopren. HS hieu: • Nguyen nhin gly ra phan iing cgng va phan iing trung hgp kieu 1,4 do ciu tao cua phan tit ankadien cd lien ke't n lien hgp. • HS van dung: • Viet dugc mdt sd phuong trinh boa hgc lien quan den ankadien. 2. KT nang • Quan sat thf nghiem, mo hinh phan tit. Riit ra nhan xet ve ciu tao va tinh chat cua ankadien. • Du doan dugc tfnh chit hoa hgc, kiem tra va ke't luan. Viet phuong trinh hoa hgc minh hoa tfnh chit hoa hgc cua buta-l,3-dien. 3. Tinh cam, ttiai do Ankadien va san pham triing hgp co nhieu iing dung trong ddi sdng san xult, lam HS tha'y dugc tim quan trgng cua viec nghien ciiu ankadien tii dd tao cho HS niem hiing thu trong hgc tap. B. CHUAN B! CUA GV VA HS • GV: - May tfnh, may chie'u, cac phie'u hgc tap. - M6 hinh phin tit butadien. - Hoa cha't, mu cao su, m6t sd vat lieu bang cao su (vdng giun...). • HS: On tap bai anken va xem trudc bai ankadien. 27 C. TIEN TRINH DAY- HOC Hoat ddng cua GV Hoat ddng cua HS Hoqt dqng 1 KIEM TRA BAI CU GV ggi 2 HS len bang trinh bay cac van de sau, cac HS khac chuan bi de nhan xet va bd sung. 1. Tiir clU tao cua anken neu tfnh chit hoa hgc ciia etilen va neu vf du minh hoa? 2. Trinh bay phuong phap hoa hgc de tach lay khf metan tinh khie't tit hdn hgp metan va etilen. HS 1: Etilen cd cl'u tao gdm 1 lien ket doi (cd lien ke't n kem ben). - Phan ling cgng hidro (phan ling hidro hoa): CH, = CH,+ H, -> CH, - CH, - Phan ling cgng brom: , CH2=CH2 + Br2(dd) -> CH2Br-CH2Br 1,2-dibrometan - Phan ling trdng hgp: nCH2 = CH2 '"•'° > (-CH2-CH2)„ etilen polietilen - Phan ling oxi hoa: 3CH2=CH2 + 4H2O + 2KMn04 -^ 3CH2-CH2+ 2Mn02i + 2K0H OH OH HS 2: Sue tit tit hdn hgp qua dung dich brom thi etilen bi hip thu: CH2=CH2 + Br2(dd) -> CH2Br-CH2Br Khf khdng bi hip thu la metan sacK 1. PHAN LOAI Hoot dqng 2 GV chie'u cong thiic ca'u tao thu ggn mot sd ankadien len man hinh. 28 HS quan sat va thao luan. CH2= C = CH2 propadien CH2= C = CH- CH3 buta-1,2-dien CH2= CH - CH =CH2 buta-l,3-dien CH2= C — CH2= CH2 CH3 3-metylbuta-l,3-dien (isopren) Yeu ciu HS nhin xet: - Dac diem chung va nit ra khai niem ankadien. - Lip cdng thiic tdng quit cua ankadien? GV yeu cau HS nghien ciiu SGK va tra. Idi cac elu hdi sau: - Co sd de phin loai ankadien. - Cd the chia ankadien thanh nhung loai nao? Cho vf du minh hoa. - Trong cac loai ankadien da neu thi loai nao quan trgng nhit? Vi sao? - Cd 2 hen ke't doi C=C trong phin tii. - Deu la hidrocacbon khong no mach hd. - Khii niem ankadien: Ankadien la hidrocacbon khdng no mach hd trong phin tied, hai lien ket doi. - Tit propadien. C3H4 ^ C3H4(CH2)k -> C3 + ,,H4 + 2k Datk = n-3- > C„H2„-2(n>3) HS nghien ciiu SGK va thao luan: - Dura vao vi trf tuong ddi gitta hai lien ket doi. - Cd the chia ankadien thanh 3 loai: + Ankadien cd 2 lien ke't doi canh nhau. Vf du: CH2=CH=CH2 + Ankadien cd hai hen ket doi each nhau 1 lien ke't don (ankadien lien hgp). Vf du: CH2= CH - CH ^CHj + Ankadien cd 2 lien ke't doi each xa nhau. Vf du: CH, CH —CH2-^ CH —CH2 Trong cac ankadien tren thi ankadien lien hgp quan trgng nhit vi cd nhieu ling dung trong thuc td'. 29 GV chie'u len man hinh c6ng thiic cl'u tao thu ggn va ten ggi eua mot sd ankadien. CH2= C = CH2 propadien CH2= C = CH- CH3 buta-1,2-dien CH2= CH-CH -CH2 buta-1,3-dien ' CH2=(p-CH2-CH2 2-metylbuta-l,3-dien GH3 (isopren) CH2=CH-CH2-CH=CH2 penta-l,4-dien Yeu ciu HS riit ra each ggi ten ankadien. HS quan sat thao luan. HS dua ra quy tic ggi ten: Ten mach chfnh • sd chi vi trf lien ke't doi -dien II. CAU TROC PHAN TC; VA PHAN UNG COA BUTADIEN VA ISOPREN Hoqt dqng 3 /. Cdu triic phdn ti butadien GV chie'u mo hinh phan tit cua buta-1,3- HS quan sat thao luan. dien len man hinh: yeu ciu HS thao luln: - Trang thai lai boa cua nguyen tii C. - Vi trf tuong ddi ciia cac nguyen tit. - Dac diem cua 2 lien ke't n. - So sanh ciu tao ciia buta-l,3-dien vdi etilen, tit dd riit ra tfnh chit hoa hgc ciia buta-l,3-dien. 30 - Cac nguyen tit C deu 0 trang thai lai hoa sp^. - 4 nguyen tii C va 6 nguyen' tii H deu nam tren mot mat phang. - Ankadien CO hai lien ke't d6i lien hgp tao nen su xen phu electron 71 tren toan bg true cacbon. - Ca hai deu cd Udn ke't doi (lien ket Tt kem ben) butadien cd lien ke't % hen hgp nen bdn hon lien ket Ti trong etilen. GV hudng din HS phan tfch ca'u tao va so sinh vdi etilen. => Tfnh chat hoa hgc ciia butadien gidng anken: Co phdn iing cgng, plidn Ung triing hgp, phdn img oxi hod khong hodn todn. Hoqt dqng 4 2. Phdn Ung cgng ciia butadien vd isopren GV chie'u lai md hinh buta-l,3-dien len man hinh va yeu ciu HS phin tfch khi cdng X2 vao buta-l,3-dien thi X cd kha nang c6ng vao cac vi trf nao, giai thfch b cIc ti le mol phan ung khac nhau? HS quan sat thao luln. Vdi ti le (1:1) X2 cd the tan cong vao: - Vi trf 1,2 pha vd 1 lien ke't Tt. - Vi trf 1,4 pha vd ca hai lien ke't Tt va tao thanh mot lien ke't doi b giiia. - Vi trf 1,3 khdng the dugc vi khSng dam bao hoa tri cho cac nguyen td. Vdi ti le (1:2) thi pha vd ca hai lien ke't doi, cgng vao tit ca cac vi tri. a) Cgng hidro GV tugng tu vdi anken ydu ciu HS viet phuong trinh hoa hgc cua ankadien vdi HS vie't phuong trinh hoa hgc tdng quit H2 va cho vf du, san phim thu dugc la gi? OnH2„ - 2 + 2H2 ',o' > Vidu: C„tl2n + 2 CH,=CH-CH=CH. + 2H, CH3—CH2—CH2—CH3 San phim thu dttgc la ankan. b) Cgng halogen vd hidrohalogen GV cho HS bie't: - Ti le % san phim cgng 1,2: 6 -SO^C khoang 80%, 40°C khoang 20% Ti le % san phim cgng 1,4: HS tuy vao nhiet do phan ting. 6 -80°C khoang 20%, 40°C khoang 80% - 0 nhiet do rl't thlp uu tien cgng 31 GV: 0 dieu kien nao thi uu tien cgng vao vi tri 1,2 hay cgng vao vi tri 1,4. GV tren co sd da phan tfch, yeu ciu HS vie't phan iing ciia buta-l,3-dien vdi brom theo cac ti le mol khic nhau. GV cho bie't tuong tu vdi anken: ankadien phan ung vdi HX tuin theo quy tac Mac-cop-nhi-cdp, va yeu elu HS vie't phuong trinh phan iing minh hoa (tao ra san phim chfnh). vao vi trf 1,2. - d nhiet do cao hon uu tien cgng vao vi trf 1,4. HS vie't phuong trinh hoa hgc. -Cgng 1,2. CH2 =CH- CH=CH2+Br -80° C CH2=CH-CH-'CH2 Br Br - Cgng 1,4. CH2=CH- CH=CH2 + Br2 """"^ > CH2-CH=CH-CH2 I 2 , 2 Br Br - C6ng ddng thdi vao ca hai lien ket doi. CH2=CH-CH=CH2 + 2Br2(du)—^ -CH- CH- CH, I I Br Br Br Br HS thao luln phan iing cgng HX. - Cgng 1,2 CH2=CH- CH=CH2+HBr -80° C CH,=CH- CH-CH, - Cgng 1,4 CH,=CH-CH=CH, + HBr Br. 40° C GV bd sung: Isopren cd phan iing tuong tu buta-l,3-dien. GV chie'u bai tap sau len man hinh cho HS thao luln: Cho buta-l,3-dien cgng HBr (1:1) cho tdi da bao nhieu san phim? La nhung san pham nao? 32 CH3-CH=CH-CH2-Br HS thao luln va tra Idi cd bdn san pham la: CH2= CH- CH2- CH2-Br CH2= CH- CH- CH3 Br HaC \ ^ CH2Br ^ C = C \ H H H ^ CH2Br GV: Tur cac phan iing trdn yeu elu HS nit ra nhin xet tfnh chit ciia buta-1,3-dien. GV hudng dan HS nit ra nhan xet. c) Phdn icng GV yeu ciu HS nhac lai khai niem phan ung triing hgp, dieu kien de cd phan iing triing hgp. GV bd sung: - Khi ed mat chit xiic tac, b nhiet do, ap suit thfch hop, buta-l,3-dien va isopren tham gia phan ung trung hgp chu yeii theo ki^u cgng 1,4 tao thanlrcac polime ma mdi mIt xich cd'chiia mdt hen ket ddi b giira. - Yeu elu yeu elu HS vie't san ph£m phan ling: H3C c = c \ H HS thao luln riit ra nhan xet: - Butadien va isopren cd kha nang tham gia phan iing cgng. - O nhiet do thlp uu tien tao thanh san phim cgng 1,2, o nhiet do cao uu tien tao thanh san phdm c6ng 1,4. - Phan ling cdng HX theo quy tac Mac-cdp-nhi-cdp. trung hop HS: - Phan iing triing hgp la qua trinh cgng hgp lien tie'p nhieu phin tit nhd gidng nhau hoac tuong tu nhau tao thanh nhitng phin tit rit ldn (ggi la polime). - Dieu kien de cd phan iing triing hgp la cd mat chit xiic tie, b nhiet do, ap suit thfch hgp. HS thao luan phan ung triing hgp la: n CH,=CH- CH=CH, t",p n CH2= CH- CH= CH2 n CH,= C - CH = CH, I CH, GV bd sung: 3-TKBGHHllNCr2 xt l".p xt '°.p (-CH2-CH= CH- CH2-)„ n CH2= C- CH= CH2 t .p (-CH2-(|:=CH-CH2-)„ CH, poliisopren 33 - San ph£m triing hgp cua buta-l,3-dien va isopren dugc ggi la cao su (cao su la chit hiiu CO cd tfnh dan hdi), cd tfnh chit gan gidng cao su tu nhien. - Tuong tu anken; ankadien cung lam ma't mau dung dich KMn04. Hoqt dqng 5 3. Dieu che, icng dung ciia butadien vd isopren GV suu tip mot sd hinh anh, miu vat ciia cac polime dugc dieu che' tii butadien va isopren chie'u len cho HS qiian sat, yeu cau rut ra ung dung ciia ankadien va vie't cong thiic ggi ten cac polime tren. GV hudng din HS neu cac phuong phap dieu che' butadien va isopren. HS quan sat thao luan. Buta-l,3-dien va isopren la monome quan trgng de tdng hop polime (cao su) cd tfnh dan hdi. (-CH2-C=CH-CH2-)„ cao su isopren CH, HS butadien va isopren didu chd' bang each tach hidro tii ankan tuong iing. CH,CH,CH,CH, — ^ CH,=CH- CH=CH, + 2H, CH3CHCH2CH3 CH, CH, --9- CH=CH, + 2H, CH, HOAT DONG 6 CONG C6 BAI VA BAI TAP VE NHA 1. Cung CO bai. GV chie'u len man hinh cac bai tip sau, yeu cau HS tra Idi d^ ciing cd kien thiic da hgc: 1. Neu tfnh chat hoa hoc co ban ciia 34 HS thao luan: - Phan ling cgng H2. - Phan ling c6ng Br2 theo kieu 1,2 va ki^u 1,4. buta-l,3-dien. 2. Vie't cdng thiic elu tao va ggi ten cac ankadien cd cdng thiic la CsHg, chi ra - Phan ling trung hgp kieu 1,4. - Phan ling oxi hoa. HS thao luan: -^H= CH-CH=CH cac ankadien lien hgp. CH3 -CH= C=CH- CH3 =9-CH=CH2 CH2 CH3 CH3 —C=C=CH2 CH3 -CH3 2(1) (2) (3) (4) CH2= C=CH-CH2-CH3 (5) CH2=CH-CH2-CH=CH2 (6) Chi CO (1) va (3) la ankadien hen hgp. 2. Bai tap ve nha 1,2, 3,4, 5, 6 (SGK) / D. HUdNG DAN GIAI BAI TAP SGK 1. a) Pollen: La nhung hidrocacbon trong phan tii cd tii hai lien ke't ddi trd len. - Dien: La nhiing hidrocacbon tfong phan tit cd tii hai lien ke't ddi trd. - Ankadien: Dien mach hd cd cdng thiic chung C„H2„-2(n > 3) ggi la ankadien. b) Ankadien dugc phan chia lam hai loai: Ankadien lien hgp va Ankadien khdng lidn hgp, c) Cdng thiic chung. cua ankadien : C„H2„-2(n>3). So vdi ankan va ahken cd ciing sd nguyen tit cacbon, ankadien cd ciing sd nguyen tur H kem ankan 4 nguyen tit H, kem anken 2 nguyen tit H. 2. a) C6ng thiic elu tao va ten ggi cac ankadien cd cdng thiic phan tit: -C4H6: CH2=C = CH-CH3 ; . CH2 = CH-C H = CH2 buta-l,2-dien buta-l,3-dien CjHg CH2=C=CH-CH2-CH3; CH2=CH-CH=CH-CH3; penta-l,2-dien penta-l,3-dien CH2^CH—CH2—CH—CH2 penta-l,4-dien 35 CH3-CH=C=CH-CH3; CH2= C= C-CH3; CH2=C=CH=CH2 CH3 CH3 penta-2,3-dien 3-metylbuta-l,2-dien. 2-metylbuta-l,3-dien b) Ddng phan tdn tai dudi dang ddng phan hinh hgc : penta-l,3-dien: H2C=CII .CH3 H2C=CH. yii H H H CH3 c/5-penta-1,3-dien rran^-penta-1,3-dien 3. a)S ; b)D ; c)S ; d) S; e) D. 5. a) Cong thiic phin tit cua A : CjHg. b) Cac du kien diu bai da cho chua du de xac dinh cong thiic ciu tao cua A, vi cd 3 cong thiic ca'u tao phii hgp: CH2= C-CH=CH2, CH3-C=C=CH2 CHj-CpH-C^CH CH3 CH3 CH3 6. Dap sd: Khdi lugng polibutadien thu dugc la 1580 kg. E. TU LIEU THAM KHAO Theo quan niem hien nay, trong phan ung cdng electrophin vao ankadien, tac nhin electrophin (H* Br,...) tin cdng vao diu mang dien Im eua mach lien hgp da bi phan cue hoa va tao ra mot cacbocation lien hgp. Br iBr + CH2 = CH-CH=CH2 Br-CH2 - CH - CH = CH2 1 2 3 4 1 2 3 4 O cacbocation nay, dien tfch duong khdng tap trung b mot nguyen tut Q ma dugc giai toa ra ca mach cho tdi nguydn tit C4 theo so dd: 5 5* Br— CH2— CH ^ ^ CH ^ ^ CH2 Vi vay, b giai doan thii hai, anion Br" cd the tan cong vao nguyen tur Q hole C4, tao ra cae san phim cgng 1, 2 va cgng 1, 4. 36 M^Br-CH2-CHBr-CH =CH2 Br—CH2—CH^^CH^^CH2 + Br - ( ^^^Br-CH2-CH = CH-CH2Br Phan ung cdng mot tie nhin bit ddi xiing (HCl) vao ankadien bat ddi xiing (isopren) xay ra theo hudng phii hgp vdi su phin bd mIt d6 electron trong phin tit, cu th^ la H* se tin cdng vao diu nao cd mat do electron cao hon trong mach lien hop cua phan tit: ^-^- ^ H^ "^f' S* Cp CH2 = C - CH = CH2 -^^ — CH3— C'' ^ CH- ^ CH2 —^ ^ CH3 CH3 - * CH3 - (p - CH = CH2 + CH3-C=CH-qH 2 Cl Cl (cdng 1,2) (cgng 1,4) 37 BAI 42 KHAI NIEM VE TECPEN A. MUC TIEU BAI HOC TKienthOc HS bie't: • Khai niem v^ tecpen va dac diem ca'u true cua tecpen. • Ngudn gdc va gia tri cua mot sd tecpen don gian de khai thac va sit dung hgp If ngudn tecpen. HS hieu: Chung cat lai cudn hoi nudc la m6t phuofng phap tach biet quan trgng trong phdng thf nghiem va trong san xua't tecpen. 2. KT nang • Phan biet dugc tecpen vdi nhirng hidrocacbon da hgc. • Du doan dugc tfnh chat hoa hgc, kiem tra va ke't luan. Viet phuong trinh hoa hgc bieu didn tfnh chit hoa hgc cua tecpen. 3. Tinh cam, thai do Viec gan ly thuye't vdi thuc tien, die biet gia tri va ung dung cua tecpen, lam nhen nhdm trong HS tinh thin ham tim hieu nghien ciru thien nhien. B. CHUAN Bj COA GV VA HS • GV: - May tinh, may chie'u, cac phie'u hgc tap. - Tranh ve hinh 6.7 SGK. • HS: Chuan bi kien thiic bai tecpen. 38 C. TIEN TRINH DAY- HOC Hoat ddng cua GV Hoat ddng cua HS Hoqt dqng 1 KIEM TRA BAI CO GV ggi 2 HS len bang trinh bay cac n6i dung sau, cac HS chuin bi de nhan xet va bd sung : 1. Ankadien dugc phan loai nhu thd nao? mdi loai cho mdt thf du. 2. Khi cho buta-l,3-dien tie dung vdi dung dich HBr (1:1), b -80°C san phim chfnh thu dugc la: A. 3-brombut-l-en. B. l-brombut-2-en. C. 2,3-dibrombutan. D. 1,4-dibrorabutan. HSl: - Cd the chia Ankadien thanh 3 loai - Ankadien cd 2 lien ke't doi canh nhau. Vf du: CH2=CH=CH2 - Ankadien cd hai lien ke't doi each nhau 1 lien ket don (ankadien hen hgp). Vf du: CH2= CH-CH =CH2 - Ankadien cd 2 lien ket doi each xa nhau. Vf du: CH2= CH-CH2-CH =CH2 HS 2 chgn dap an diing. Dap In A. I- THANH PHAN, CAU TAO VA DAN XUAT Hoqt dqng 2 /. Thdnh phdn GV HS quan sat thao luln. chie'u len man hinh hinh 6.7 SGK (hole tranh ve hinh 6.7 SGK) cho HS quan sat. 39 Tinh diu thong, sa, que', chanh, cam... CioHifi: a-tecpinen, P-tecpinen, a-pinen. C15H24: a-eedren, P-cedren, a-selinen. C40H56: caroten, licopen. Yeu ciu HS nhin xet: - Cong thiic chung ciia tecpen. - Thanh phin phin tur. - Khai niem tecpen. - Cong thiic chung (CsHg)^ n>2. - Gdm cd C, H la hidrocacbon khSng no - Tecpen la hidrocacbon khdng no thudng cd c6ng thiic chung la: (CjHg)^ n>2. 2. Cdu tao G V viet c6ng thiic elu tao cua mot sd tecpea HS quan sat thao luln. miaxen oximen limonen caren a-pmen P -ipinen 40 P - caroten (mau vang,^ trong cu ca rdt). licopen (mau do, trong qua ca chua). yeu elu HS nhan xet die diem ciu tao cua cac tecpen tren. Phin tit tecpen cd ca'u tao mach hd hoac vdng va cd chiia cac lien ket doi C=C. 3. Mot vdi ddn xudt chita oxi cua tecpen GV gidi thieu m6t din xul't vai chiia oxi cua tecpen, yeu clu HS nhan xet ve die diem cl'u tao va iing dung? Loai mach hd: CH2OH CH2OH geraniol xitronelol Geraniol cd trong tinh diu hoa hdng. Xitronelol cd trong tirih diu sa. mentol menton - Mentol va menton cd trong tinh diu bae ha. Mot sd din xult khac. HS thao luln va nhan xet. - Cl'u tao mach hd khong no trong phin tit cd mot nhdm OH. - IJiig dung la nhung don huong quy diing trong cong nghiep huong lieu va thuc pham. - Cl'u tao mach vdng cd chiia oxi. - Uig dung trong cong nghiep thuc pham va dugc pham. 41 CHO geranial CHO xitronelal CH2OH retinol (vitamin A, C20H29OH ). .C l-feOH phitol 0 dang este cd trong diep luc. II-NGU6 N TECPEN THIEN NHIEN Hoqt dqng 3 /. Nguon tecpen thien nhien GV yeu elu HS nghien ciiu SGK va tra Idi cac van de sau: - Tecpen cd b dau? - Neu cong thiic phan tit mdt so tecpen thong dung. 42 HS thao luan. - Tecpen va din xult cd chua oxi cua tecpen thudng gap trong gidi thuc vat. Chiing cd b trong la, than, hoa, qua hoac rd. I^Tgoai ra edn cd trong co the d6ng vat. + Tecpen cdng thiic CioHig, C15H24 cd trong qua, la va nhua loai thdng. + Squalen C30H50 cd trong dau gan ca. + Caroten va licopen C40H56 la sac td mau dd cua ca rdt va ca chua chin. + Retinol (vitaminA: C20H29OH) cd trong long do triing va diu gan ca... 2. Khai thac tecpen GV gidi thieu: Phuong phap hay diing de khai thac tecpen la phuong phap chung cit Idi cudn hoi nude (hinh 6.8 SGK). GV hudng din HS phan tfch dac diem cl'u tao cua tecpen, tii dd giai thfch tai sao lai hay diing phuong phap chung cl't Idi cudn hoi nude. GV bd sung: Chumg cl't loi cudn hoi nudc la m6t phuong phap tach biet quan trgng trong phdng thf nghiem va trong san xul't. / GV gidi thieu mdt sd co sd san xult tinh diu trong nudc ta. 3. lfng GV suu tip miu vlt, tranh, anh mot sd ling dung CO ban cua tecpen. Chieu len man hinh cho HS quan sat (hole cho HS nghien cuu SGK). Yeu elu HS khai quit ung dung cua tecpen. HS quan sat. HS: Tecpen va din xult chiia dxi (tinh diu) cd thanh phin chfnh la hidrocacbon nen hau nhu khong tan trong nudc, nhe hon nudc va cd nhiet do sdi tuong ddi thlp => de bay hoi. dung HS quan sat (hoac nghien ciiu SGK). Tecpen cd iing dung: - Lam huong lieu trong cdng nghiep ml phim. - Lam nguyen lieu trong cdng nghiep thuc pham. 43 - Tecpen va din xult cua tecpen edn diing de san xult dugc phim. Hoqt dqng 4 CONG CO BAI VA BAI TAP VE NHA 1. Cung cd' bai GV khic sau kie'n thiie cho HS ve: • Dac diem clu tao cua tecpen va din xuat cua tecpen . - Mach hd hoac mach vdng. - Co chiia cac lien ke't doi trong phan tur. • TJhg dung cua tecpen va din xult ciia tecpen. Cd ung dung quan trgng trong cong nghiep: mi phim, thuc phim., dugc phim. 2. Bai tap ve nha 2, 3, 4, 5, 6 (SGK) D. HU(3NG DAN GIAI BAI TAP SGK 2. Cong thiic cua oximen va limonen oximen limonen 3. Do cdng thiic phin tit oximen va limonen cd 10 nguyen tit C nen b dieu kien thudng oximen va limonen d trang thai long, ft tan trong nudc, tan trong mdt sd dung moi hiru co. De tach chiing cd the diing phuong phip chumg cl't Idi cudn hoi nude. 4. a) S ; b) S ; c) D ; d) D ; e) D'; g) S ; h) S ; i) D ; k) D. 44 5. Phuong trinh hda hoc la: + 2H 2(du) + 2Br 2(dii) CH,OH + Na CH,OH + Br, CH,ONa + 1/2 H, 4J BAI 43 ANKI N A. MUC TIEU BAI HOC 1. Kien thdrc HS biet: • Khai niem, cong thiic chung cua day ddng dang ankin, biet phin loai va ggi ten mot sd ankin don gian. • ca'u tao, tfnh chit hoa hoc dac trung cua ankin, dieu che' va m6t sd ling dung cua ankin. • Cach phin biet ankan, anken vdi ankin bang phUOng phap hoa hgc. HS hieu: Nguyen nhan gay ra phan iing the' ion kim loai, phan iing triing hgp va phan oxi hoa khong hoan loan la do cau tao cua phan tix ankin cd lien ket ba (gdm 2 lien ke't Tt va mot lien ket 0). 2. KT nang • Quan sat thf nghiem, md hinh phan tii ankin, nit ra nhan xet ye cau tao, tfnh chat cua ankin. • Tur cdng thiic biet ggi ten va ngugc lai tut ggi ten viet dugc cdng thiic nhiing ankin don gian. • Vie't phuong trinh hoa hgc minh hoa tfnh chat hoa hgc ciia ankin. 3. Tinti cam, thai do Ankin cd nhieu phan iing mdi la, vi vay viec nghien ciiu ankin tao cho HS niem hiing thu trong hgc tip, kfch thfch su sang tao. B. CHUAN Bj COA GV VA HS • GV: - May tfnh, may chie'u,. cac phie'u hgc tap. - M6 hinh phin tit axetilen. - Hoa chit: CaQ, nudc brom, dung dich AgN03, dung dich KMn04, dung dich NH3, nUdc cat. 46 - Dung cu: Ong nghiem, niit cao su kem dng din khf, kep dng nghiem, den edn va bg gia thf nghiem. • HS: On tap kie'n thiic ve anken va xem trudc bai ankin. C. TIEN TRINH DAY- HOC Hoat dpng cua GV Hoat dpng cua HS I. DONG OANG, DONG PHAN, DANH PHAP, TINH CHAT VAT Ll VA CAU TROC Hoqt dqng 1 /. Dong ddng, dong phdn, danh phdp GV chie'u cong thiic clu tao thu ggn cua m6t sd ankin len man hinh va yeu clu HS nhin xet riit ra khai niem ankin. CHsCH; CH3-C=CH; CH3-C=C-CH3 GV dat ra cac vl'n de sau yeu clu HS tra Idi: - Anken cd nhitng kieu ddng phan cl'u tao nao?' - Tuong tu anken yeu clu HS neu cac kieu ddng phin ciia ankin. GV ydu clu HS viet c6ng thiic ddng phin ciia ankin cd c6ng thiic CjHg. HS quan sit, thao luln va nhin xet. - Dac diem chung cua cac hgp chit la cd mdt ndi ba trong phin tur. - Ankin Id hidrocacbon khong no mach hd, trong phdn tic co chita mot lien ket ba. C2H2;C3H4;C4H,...C„H2„-2 (n>2) HS thao luln. - Anken ed cac kieu ddng phan cl'u tao : + Ddng phin niach C. + Ddng phan vi tur lien ke't doi. - Gid'ng anken la ankin cd ddng phan ca'u tao nhung khong cd ddng phan cis trans. CsHg: CH3-CH2- CH2-C=CH CH3—CH2— C=C — CH3 CH3-CH- CsCH CH, 47 GV chie'u len man hinh bai tap. Quan he sd ddng phan clu tao cua anken CjHio (x) va ankin CjHg (y) la A. X > y B. X < y C. X = y D. Ca 3 trudng hgp tren GV chie'u len man hinh cong thiic clu tao va ten ggi thong thudng mot sd ankin sau: HS thao luln, tra Idi: Dap an A. HS thao luan dua ra ke't qua: CH =CH, CH3-C^CH CH3-C^C-CH3 ,CH3-CH2-C=C-CH3 CH =CH CH3 - C ^ CH CH, — C = C— CH, CH3—CH2—C:=C—CH3 axetilen metylaxetilen dimetylaxetilen Yeu clu HS riit ra quy tie ggi ten thdng thudng cua cIc ankin va ggi ten cac ankin cd cong thiic CjHg. GV chie'u len man hinh bang 6.2 SGK cho HS qiian sat (hoac cd the cho HS nghien ciiu bang 6.2 SGK). Yeu clu HS: - Neu quy tac ggi ten thay the cua ankin. - Cach chgn mach chfnh. 48 etylmetylaxetilen Ten thdng thudng: + Ten gdc ankyl lien ket vdi nguyen tit C eua lien ket ba + axetilen. (Cac gdc ankyl dugc ggi la theo thii: tu chii cai diu tien cua ten ggi chiing). HS vie't ddng phin va ggi ten. CH3-CSC-CH2-CH3 etylmetylaxetilen CH3—CH2—CH2—C=CH propylaxetUen CH3-CH-C=CH CH, isopropylaxetilen HS quan sat thao luln. Quy tac: Sochi vi tri nhanh + ten nhanh + ten mach chinh + sd chi vi tri lien ket ba + in - Cach danh sd. - Cach ghi chi sd lien ke't ba. Yeu clu HS ggi ten cac ankin cd cdng thiic CgHio - Chgn mach C dai nhit cd chiia lien ke't ba. - Dinh so thii tu tii phfa gin hen ket don - Sd chi vi trf lien ke't ba ghi ngay trudc duoi in. HS vie't ddng phin va ggi ten: CH3-CH2-CH2-CH2- C^CH hex-l-in CH3-CH2-CH2-CSC-CH3 hex-2-in CH3-CH2-C=C-CH2-CH3 hex-3-in CH3-(;:H-CH2-C=C H 4-metylpent-l-in CH3 CH3-CH-C=C-CH 3 4-metylpent-2-in CH, CHJ-CHZ-CH-C^C H 4-metylpent-l-in CH, C^H3 CH3- C- C=CH 3,3-dimetylbut-l-in CH3 Hoqt dqng 2 "^ 2. Tinh chdt vqt li GV chie'u bang 6.2 trang 175 len main hinh, yeu clu HS nhin xet. Hoqt dqng 3 3. Cdu true phdn tvc GV chie'u m6 hinh phan tut axetilen len man hinh. Yeu clu HS thao luln: HS thao luln va tra Idi. 4-rKBGHHnNCT2 49 - Viet cong thiic electron cua axetilen, tur dd neu cl'u tao cua lien ke't ba. - Trang thai lai hoa cua C trong lien ke't ba, gdc lidn ket HCC. - Vi trf tuong ddi cua cac nguyen tii. - Rut ra tfnh chit hoa hgc cd thd cd ciia ankin. - Cdng thiic electron: H:C:iC: H H - C= C - H ca'u tao ciia lien ket ba gdm hai lien ket Tt va mot lien ke't cr d gifla. - Nguyen tit C d trang thai lai hoa sp. Gdc lien ket HCC la 180°. - Hai nguyen tit C va hai nguyen tix H Cling nam tren dudng thang. Tinh chat hoa hgc cua ankin: + Do clu tao gdm hai lien ke't Tt kem ben viing nen ankin cd phan iing cdng gidng anken, ankadien. + Hai lien ke't Tt nim tren ciing hai nguyen tii cacbon lam phan cue lien ke't C-H nen ank-l-in cd phan ling the' ion kim loai (hay kim loai). II. TINH CHAT HOA HOC Hoqt dqng 4 /. Phdn vcng cgng a) Cgng hidro GV yeu clu HS phin tich clu tao cua ankin, kha nang phan ung cua ankin vdi H2. GV ggi y HS: phan ung cua ankin vdi H2 xay ra qua 2 giai doan theo so dd: C2H2 +H, ^C2H 4 +H, -^QHfi Ni ' "2**4 Ni Yeu clu HS vie't phuong trinh hoa hgc minh hoa so ddtren. 50 HS thao luln va tra Idi: - Ankin cd 2 lien ke't TI kem ben cd kha nang cdng H2 di pha vo tumg lien ke'tTt. - Khi cd xiic tac Ni thi phan iing xay ra qua 2 giai doan: Giai doan 1: tao anken CH sCH + H, ^ CH,=CH, Giai doan 2: tao ankan CH2=CH2 + H2 - ^ CH,-CH, GV bd sung: Mudn" phan iing dittig b giai doan 1 thi ddng xiic tac thfch hgp (Pd/PdC03 xuc tac nhiem dgc giam kha nang xiic tac) phan iing dumg lai b giai doan 1 tao anken. GV yeu clu HS vie't phuong trinh hoa hgc. GV yeu clu HS lip so dd tdng quat ciia ankin vdi hidro va vi^t phuong trinh hoa hoc minh hoa. HS viet phuong trinh hoa hgc. CH =CH + H2 ^'^;^' > CH2 = CH2 HS vie't so dd: +H. M>CH•n^-^2, n Ni '^^n'^^2n+2 -iibl2ii-2 Ni C„H2„-2+ H Ni ^C„H •n^-^2n GV lam thf nghiem: C„H2„ +H2 Ni •> C„H, 'n^^2n+2 b) Cdng brom HS quan sat thao luln. Cho vai miu nhd canxicacbua vao d'ng nghiem da dung 1ml H2O va dly nhanh bang niit cd d'ng din khf diu vudt nhgn, din khf thoat ra vao dung dich Br^. Yeu clu HS neu hien tugng va giai thfch bang phuong trinh hoa hgc. GV bd sung: Giai doqn sau xdy ra kho hon giai doqn trudc. Noi chung ankin ldm ma't mdu dung dich brom cham hon anken. Hien tuqng: ban diu cd khf thoat ra, khf dd lam nhat dung dich brom. Gidi thich: Khi thoat ra la axetilen da phan ling vdi dung dich Br2 theo hai giai doan lien tie'p. CH-C H + Br2-^CH = CH I I Br Br 1,2-dibrometen CH = CH + Br2 - Br -CH - CH- Br I I ^ I I Br Br Br Br 1,1,2,2-tetrabrometan 51 GVyeucauHS: c) Cgng hidroclorua HS thao luln. - Vie't cac phuong trinh hoa hgc cua ankin vdi HCl. GV ggi y: Phan ung nay cung xay ra qua hai giai doan va giai doan sau khd khan hon giai doan trudc. GV hudng din HS vie't phuong triiih hoa hoc eua axetilen vdi HCl. - So sanh vdi phan iing c6ng Br2, H2 cho vf du minh hoa? + Ankin cgng HX xay ra qua 2 giai doan lien tie'p. CH^ CH + HCl -^ ^ CH2 = CHCl vinyl clorua CH2 =CHC1 + HC1^^CH 3 - CHCI2 1,1-dicloetan + Khi cd xiic tac thfch hgp ankin tie dung vdi HCl sinh ra din xul't monoclo cua anken. CH^CH+HCl HgCl; ^ CH, = CHCl + Khac vdi cgng H2, Br2. Ankin bat dd'i cgng HX tuan theo quy tac Mae c6p-nhi-c6p CH,-C=CH + HC1 CH3 —C ^CH2 Cl CH3-CH=CH2+ HCI-CH3-CCI2-CH3 2,2-dicloetan GV gidi thieu cho HS bie't: d) Cgng nudc (hidrat hod) HS lang nghe va vid^t phuong trinh boa - Khi cd mat HgS04 trong mdi trudng axit thi ankin cd th^ cgng H2O tao ra hgp chit trung gian khdng ben va chuyln thanh andehit hoac xeton. - Phan ung cdng nudc cung xay ra theo quy tac Mac-cdp-nhi-cdp. GV yeu elu HS vie't phuong trinh hoa hgc cua etin va propin vdi nudc. 52 hoc. CH=CH+H20-!Ma^[CH2=CH-OH] I khdng b^n CH3CHO-^ GV hudng din HS nhin xet phan iing cdng hgp cua ankin vdi nudc so vdi phan ung cdng H2, Br2, HCl. (^H3 CH3-C=CH+H20^^^^^^[CH2=C-OH] I khdng bdn CH3-CO-CH3 HS nhin xet: Phdn Ang cgng hqp vdi nudc chi xdy ra vdi ti le mol (1:1). e) Phdn utngdime vd trime hod GV hudng din HS vie't phuong trinh hoa hgc: xem axetilen (H-C=CH) nhu mot H-X va yeu clu HS vie't phuong trinh hoa hgc diine va trime cua axetilen. HS thao luln va vie't phucmg trinh hoa hgc: Hai phin tii axetilen cgng hgp. CH^CH + H-C=CH '"•'° > CH2=CH-C= CH vinylaxetilen Ba phin tit axetilen c6ng hgp. 3QH2 -^^^^ QH, (ff^ ) benzen Hoqt dqng 5 2. Phdn icng the bang ion kim loai GV lam thf nghiem: Sue khf axetilen vao dung dich AgNOj trong dung dich NH3 (da dugc chuin bi san: Nhd tii tut dung dich AgN03 vao dung dich NH3 va lie de'n khi dung dich trong sudt). GV yeu clu HS: Quan sat va neu hien tugng. GV neu vin de: So vdi ank-l-in thi ank-2-in khSng cd hien tugng gi xay ra, tai sao lai cd su khac nhau nhu vay? GV hudng din, diin khi6n HS giai HS quan sat va nhan xet. Hien tugng: Cd ket tua mau vang xuat hien. HS tham gia giai quye't vin de: 53 quyet vin di. Yeu clu HS: - So sanh caii tao cua ank-l-in vdi ank-2-in. - So sanh su phan cue lien ket C-H trong C ndi ba vdi cac lien ket C-H khac. - Kha nang phan .ling cua H lien ket O C . - Vie't phuong trinh hoa hgc minh hoa. Tuong tu yeu clu HS vie't phuong trinh hoa hgc cho propin. GV hudng din HS ket luan vin de, yeu clu HS neu ung dung cua phan ling tren? - So vdi ank-l-in thi ank-2-in khong cd H lien ke't vdi (>C. - Lien ke't C-H cua( OC-H ) bi phan cue manh nhit do lien ke't ba tip trung mIt do eletron cao nhit. - Do bi phin cue manh nen lien ket C-H cua ank-l-m phin cue manh, nguyen tit H cd tfnh linh ddng cao dd bi thay the'bdi ion bac(Ag'^). HC^CH + 2AgN03 + 2NH3 -> AgC=CAg>l'+ 2NH4NO3 bae axetilua (mau vang) CH3-C-CH +AgN03+NH3 -^ CH3-C=CAg>l'+NH4N03 Ket luan: chi cd ank-l-in mdi cd phan ling hoa hgc vdi AgNOj tao ra ket tua. Ung dung tfnh chit tren dugc diing de phan biet ank-l-in vdi anken, ankadien va ankin khac. Hoqt dqng 6 3. Phdn Ung oxi hod a) Phdn icng oxi hod hodn todn GV lam thf nghiem ddt chay axetilen trong khdng khf. Ydu clu HS viet phuang trinh phan ung chay cua ankin va nhan xet ve: - Hien tugng. - Ti le sd mol H2O va CO2. - Nhiet lugng toa ra. 54 HS quan sat, nhin xet. - Axetilen chay cho nggn Ifta mau xanh nhat. C2H2+-O2 2CO2 + H,0 C„H2„-2+^02^^nC02+(n-l)H2O ^CO, '^ '^H,0 • Phan ling chay toa nhieu nhiet. b) Phdn iing oxi hod-khong hodn todn GV lam thf nghiem: Sue khf axetilen vao dung dich thudc tun (BCMn04) yeu clu HS: - Neu hien tugng. - Giai thfch. GV hudng din HS viet phuong trinh hoa hgc (minh hoa). GV nhan xet: Phdn icng ldm mdt mdu dung dich thudc tim co the diing de nhdn bie't cdc dnkin. So vdi anken phdn ling ndy xdy ra chdm hon. HS quan sat va thao luan: - Hien tugng dung dich thudc tfm nhat mau din ddng thdi xul't hien ket tua mau nlu (Mn02). - Giai thfch ankin cd lien ket Tt kem bdn nen phan ung vdi KMn04 gidng anken va ankadien. Phugng trinh hoa hgc: 3CH^CH+8KMn04- 3(OOOK)2+2KOH + 8Mn02i+ 2H2O OI^U CHE VA UNG DUNG Hoqt dqng 7 /. Dieu che GV gidi thidu: Phuong plhap dieu che' axetilen trong cong nghiep la nhiet phin metan b 1500°C, yeu clu HS viet phuong trinh hoa hgc. GV bd sung: Ngoai ra ngudi ta edn dieu che' C2H2 tiit than da va da voi. GV hudng din HS viet phuong trinh hoa hoc didu che' dit den. HS: Axetilen dugc san xua't chu yeu tut metan. 2CH4 -^^^ ^ C2H2+ 3H2 HS vie't phugng trinh hoa hgc: CaCO, ^ CaO + CO, CaO + 3C 16 dien > CaQ + CO 55 GV lam thf nghiem di^u che' axetilen tut dl't den CaQ: Cho vao trong binh tam giac mdt ft dit den CaQ, trong binh cd chiia sin mot ft nudc. Dly nhanh bang niit cao su ed gan dng thuy tinh vudt nhgn, cho HS quan sat va th^ mot sd tfnh chit vlt If. GV yeu clu HS: - Viet phuong trinh phan ung. - Khi thoat ra cd tfnh chit gi (mau, mui) - Giai thich. GV bo sung: Phuong phdp dieu che cdc chdt tic than dd vd dd voi ngdy ndy it duqc dang vi khong kinh te. 2. lfng GV: tiir tfnh chit hoa hgc cua ankin, yeu clu HS neu ung dung. GV: Cd the suu tip tranh anh, miu vat chie'u len man hinh cho HS quan sat, lam phong phu ung dung cua axetilen. HS quan sat va thao luan: - Phuong trinh hoa hgc. CaC2 + 2H2O -> Ca(OH)2 + C2H2 - Khf thoat ra kh6ng mau, cd miii - Giai thfch khf thoat ra cd mui do dit den cd lin nhieu tap chl't cua luu huynh, nito ndn tao ra Idif cd miii nhu H2S, NH3. dung HS thao luan: - Axetilen chay toa nhieu nhiet nen dugc dung lam nhien lieu. Vf du: - Den xi oxi-axetilen dung han, cat kim loai. - Mdt so thie't bi tao nggn lira cho nhiet do cao. - Cac phan iing cdng, trime, dime va trung hgp dugc iing dung trong qua trinh tong hgp cac hgp chit huu ca. Hoqt dqng 8 CClNG CO BAI V A BAI TAP VE NHA 1. Ciing cd bai GV: Chia HS thanh 4 nhdm phat cac phie'u hgc tap co cac noi dung sau: 56 Phieu 1: Dot chay hoan toan 3 ankin A. B. C thu duge 3,36 1ft CO2 (dktc) va 1,8 gam H2O. vay tdng so mol cua 3 ankin la: A. 0,15 B. 0,25 C.0,08 D. 0,05 Ddp dn D. Phieu 2: Bang phuong phap hoa hgc. Hay phan biet etan, etilen va axetilen. HS thao luan: - Din ca ba khf vao dung dich AgNO,/NH3, khf nao tao ke't tua mau vang thi khf dd la C2H2. - Din hai khf edn lai qua dung dich brom, khf lam nhat mau dung dich brom la QHj. - Con lai la etan. •Phieu 3: Chat hiiu co X cd c6ng thiic phan tur CgHg mach hd kh6ng phan nhanh. Bie't 1 mol X tac dung vdi AgN03/NH3 du tao ra 292 gam ke't tua. X cd cong thiic elu tao nao dudi dly. A. CH=C-C=C-CH2-CH3 B. CH=C-CH2-CH=C=CH2 C. CHSC-CH2-OC-CH3 D. CH=C-CH2-CH2-C=CH Ddp dn D. Phie'u 4: Trong mdt binh kin chiia hidrocacbon X va hidro, nung ndng binh de'n khi phan ung hoan toan thu dugc ankan duy nhit. 0 ciing nhiet do, ap suat trong binh trudc khi nung gip ba lin ap suit trong binh sau khi nung. Dot chay mdt lugng Y thu dugc 8,8 g CO2 va 5,4 g H2O. Cong thiic phin tur cua X la: A.C2H2 B. C2H4 C. C4H6 D. C3H4 Ddp dn A. 2. Bai tap ve nha 1, 2, 3, 4, 5, 6 (SGK) D. HUdNG DAN GIAI BAI TAP SGK 1. Dinh nghia sai: A, B, C; dinh nghia dung : D, E. 2. Cac c6ng thiic clu tao eua hidrocacbon mach hd vdi cong thiic CjHg. CH=C-CH2-CH2-CH3; CH3-C=C-CH2-CH3; CH=C-(pH-CH3 CH3 (A) pent-1-in (B) pent-2-in (C) 3-metylbut-l-in 57 CH2=C=CH-CH2-CH3; CH2=CH-CH=CH-CH3; CH2=CH-CH2-CH=CH2 (D)penta-l,2-dien (E)penta-l,3-dien (F) penta-l,4-dien CH3-CH =C=CH -CH3. CH2=C-CH=CH2 CH3-C=C=CH2 CH3 CH3 (G) penta-2,3-dien (H) 2-metylbuta-l,3-dien (I) 3-metylbuta-l,2-dien (A) va (B) la ddng phin vi trf lien ke't ba. (A) va (C), (B) va (C) la ddng phan mach cacbon. (D), (E), (F), (G) ciing nhu (H), (I) la ddng phan vi trf lien ket doi. (D), (E), (F), (G) la ddng phan mach cacbon vdi (H) va (I). (A), (B), (Q va (D), (E), (F), (G), (H), (I) la ddng phan nhdm chiic. 3. Cac phuong trinh hoa hgc: a) CH3 - CsCH + 2H2 -^ ^ CH3- CH2- CH3 b) CH3 - C = CH + H2 ^^'^°') CH3- CH = CH2 c) CH3 -C = CH + Br2 _^"4 > CH3-CBr =CHBr d) CH3 - C = CH + 2Br2 g^ > CH3- CBr2 - CHBr2 e) CH3 - C=CH + AgNOj + NH3 "'° ) CH3 - C^CAg i + NH4NO3 g)CH3-C=C H + 2HCl(k) ^ CH3-CCI2-CH3 h) CH3 - C= CH + HOH "^''^"') CH3 - C -CH3 0 4. a) Dung dung dich AgN03 /NH3 nhan ra QHj: Co ke't tua mau vang nhat. Dimg nudc brom nhan ra C2H4 (lam mlt mau nudc Br2), con lai la etan. b) Diing dung dich AgN03/NH3 nhin ra but-1-in (cd ke't tua vang nhat), edn lai la butadien. c) Dung dung dich AgN03 /NH3 nhin ra hut-1-in (cd ke't tua vang nhat), con lai la but-2-in. 5. a) Phuong phap di tur CH4 dugc diing nhidu vi CH4 cd nhi^u trong khf thien nhien va san pham che' bie'n diu md, edn phuong phap di tii da vdi ton ning lugng nhieu ban, cho khf axetilen cd lin nhi^u tap khf (H2S, NH3, PH3 ) la nhung khf dgc cd hai, gia thanh cao hon. 58 b) CH^CH i2g > CH2=CH-C1 ! 50-200° C,xlHgCl2 '• 500°C -HCl CH2=CH2 ^^'' > CH2CI-CH2CI c) Phuong phap di tiir etilen cho san ph&n re hon vi CH2 = CH2 cd san trong khi crackinh edn CH^CH phai didu chd' tur CH4 b 1500°C tdn nang lugng nen dat hon. 6. Phuong trinh hoa hgc: 2CH4 "°°°^ > CH=CH + 3H2t (1) HCsCH + 2[Ag(NH3 )2]0H -> Ag-OC-Ag 4 + 2H2O + 4NH3 (2) a) Theo phuong trinh hoa hgc (1) ne'u ggi sd mol C2H2 sinh ra la x thi: 3 36 Sd mol h6n hgp khf sau phan iing nhi?t phan la : —— + 2x = 0,15 + 2x Theo diu bai the tfch hdn hgp giam 20% la the tfch C2H2 : -i^i22^ = 20% 2x + 0,15 tfnh ra dugc x = 0,05 mol. Ne'u phan iing dat hieu suit 100% thi sd mol C2H2 la ——mol. Vly hieu suit ,.' ^ ,:•- , . ,^ 0,05.100% ^^^^ „ phan ung nhiet phan la: « 66,67% b) % Vc^H^ = 20% ; VH^ = 60% ; % V^H^ = 20% c) Cho hdn hgp qua dung dich AgN03/NH3 du, thu liy dung dich rdi cho phan ling vdi dung dich H2SO4 loang du, thu ditgc C2H2. 59 E. TU LIEU THAM KHAO SO DO DIEU CHE CAC SAN PHAM CONG NGHIEP T U AXETILEN polivinyl axetat polivinyl ete axit axetic_ _^ etyl axetat ,H,OH CH2=CH (icocH polivinylclorua CH2=CHC1 CH,=CH-CN* polivinylnitrin CH2=CH-CO-X CH,CHO- -«CH3-CH-CH2-CH2 OH OH CH2=CH—CH—CH2 buta-l,3-dien •CH,=CH-C=CH cao \ su Buna 2=CH-CO-CH3 vinylmetyl xeton iCH=CH) „ pollen (X= OH, OR, -NH2) CH2-CH=CH-CH axit acrylic va din xult QJJ OH HOCH2CH2CH2CH20H_ buta-l,4-diol axit sucxmic HOOC-(CH2)4-COOH axit adipic Nilon-6,6 <- 60 CI2CH-CHCI2 tetracloetan tetra hidro furan NC-CH2CH2CH2CH2-CN adiponitrin - H2N-(CH2)6-NH2 hexametylen diamin BAI 44 LUYEN TAP HIDROCACBON KHONG NO A. MUC TIEU BAI HOC l.Klentfiac HS bie't: • Su gid'ng nhau va khac nhau vd tfnh chit giita anken, ankin va ankadien. • Cach phin biet ankan, anken, ankadien bang phuong phap hoa hgc. HS hieu: • Md'i lien quan gifla cl'u tnic, tfnh cha't hoa hgc dac trung ciia hidrocacbon • khdng no va phuong phap dieu che' cua anken, ankin va ankadien. 2. KT nang • Tfl cong thiic clu tao bie't ggi ten va ngugc lai tii ten ggi vie't dugc cong thiic cl'u tao cua nhflng anken, ankin, ankadien don gian. • Ren luyen kl nang so sanh, tim md'i lien he gifla thiic co ban giua anken, ankin va ankadien de tfl dd cd each nhd he thdng. • Vin dung kie'n thfle da hgc tfl dd bie't each giai dung bai tap. B. CHUXN Bj cClA GV VA HS • GV: - May tfnh, may chie'u, cac phie'u hgc tap, he thdng bai tap on tap. - Bang so dd chuyen hoa gifla ankan, anken ankin va ankadien. • HS: On tip cac kie'n thiic If thuyet, phuong phap giai bai tip ve anken, ankadien, ankin. 61 C. TIEN TRINH DAY- HOC Hoat dpng cua GV Hoat ddng cua HS 1- KIEN THU C CAN NAM VONG Hoqt dqng 1 /. Cdu trdc GV neu cac vl'n de co ban da hgc: - Khai niem anken, ankadien, ankin. - Dac diem cl'u tnic lien ke't cua anken ankadien, ankin. - Tmh_chlt hoa hgc co ban cua hidrocacbon khdng no. - Phucmg phap dieu che' va iing dung ciia anken, ankadien, ankin. GV chia HS theo cac nhdm (4 nhdm) va giao noi dung luyen tip cho cac nhdm. GV: yeu cau HS (nhdm 1) neu cdng thfle tdng quit va cl'u true cua anken, ankadien, ankin. HS thao luln: Anken l.CTTQ QH2„ (n>2,nGN* ) 2. Clu triic nguyen tfl C ciia lien k^c d6i b trang thai lai hoa sp^. Cac nguyen tii lien ke't vdi C ndi doi nam tren cung mdt mat phang; R, R, Ankadien C = C R. R. l.CTTQ C„H2„-2 (n>3,nEN* ) 2. ca'u true 4 nguyen tut C cua lien ke't doi or trang thai lai hoa sp^. Cac ngiiyen tfl lien ke't v ^ C ndi d6i nam tren cung m6t mat phSng. 62 R u .^3 ^ C = C ^ / « C = C R, Ankin R, R. l.CTTQ C„H2„-2 (n>2,nGN) 2. Clu tnic nguyen tfl C cua lien ket ba b trang thai lai hoa sp. Cac nguyen tfl lien ke't vdi C ndi ba nam tren cung dudng thang. Rl — C = C — R, 2. Tinh chdt vat li GV yeu c^u HS (nhdm 2) ndu tfnh chit vlt If cua cac hidrocacbon kh6ng no, quy lull bien ddi t^s, t'nc. HS thao luln. - Tfl Q - C4 6 the khi, tfl C5 trd di d the long hoac ran. - Hidrocacbon la hgp chat khong mau, khdng tan trong nudc, nhe hon nude. - t°s, t°nc tang din khi sd nguyen tur C tang. - Anken, ankin, ankadien khong cd mui, edn tecpen cd mui dac trung. 3. Tinh chdt hod hoc GV ydu clu HS (nhdm 3) neu tfnh chit hoa hgc cua cac hidrocacbon khdng no, so sanh kha nang c6ng brom cua anken va ankin. HS thao luln. a) Phan ling e6ng: - C6ng hidro khi cd xuc tac (Ni, Pt, Pd) va nhiet d6 thfch hgp thi deu bi hidro hoa thanh ankan tuong iing., Rieng ankin phan iing cdng xay ra theo hai giai doan, mudn phan ting dflng b giai doan 1 thi dung xuc Fd/PbCO^, san phim la anken. - Cdng halogen deu lam mat mau dung dich brom va bi halogen boa thanh din xult di hole tetra halogen. 63 GV yeu clu HS (nhdm 4) neu phuong phap dieu che' va iing dung cua cac hidrocacbon khong no. 64 Tdc do c6ng brom cua anken nhanh hon ankin khoang nam lin, ankin cd kha nang c6ng nhidu brom hon anken. - Cgng HX theo quy tic Mac-cop-nhi cdp: hidrocacbon khdng no cd kha nang cgng HX phan iing cgng thi hudng tin cong ciia X vao C ndi doi, ndi ba cd bic cao hon se la san pham chinh. Ankadien cgng theo kieu 1,2 va 1,4. b) Trung hgp: Khi cd xuc tic phii hgfp va cd nhiet do, ap suit thi'anken va ankadien diu day ddu dd trung hgp thanh polime, ankin khdng bi triing hgp ma chi bi dime hoa, trime hoa... c) Oxi hoa: ta't ca deu lam mi't mau dung dich thudc tfm; Chay manh va toa nhieu nhiet n^-Q ^ Ujj 5 d) Rieng ank-l-in cd phan iing the'nguyen tfl H cua C ndi ba bang ion bae. HS thao luan va tra Idi. a) Dieu che': - Trong cdng nghiep san xult anken, ankin va ankadien chu ye'u tfl ankan diu md. - Trong phdng -thf nghiem axetilen dugc dieii che'tfl dit den (CaC2). Cdn etilen dugc dieu che' tfl ancol etylie. b) Oig dung: - Anken, ankadien chu ye'u dung d^ san xult polime lam chit deo, cao su. - Anken va ankin duge dung lam nguyen lieu de san xult cac din xuat cua hidrocacbon. - Ankin cdn dugc sfl dung la nhidn lieu den xi. Hoqt dqng 2 II. BAI TAP GV chie'u bai tip 1 (SGK) len man hinh de HS thao luln. ) cae so thfch hgp vao bang sau: 1. a) Hay dientie' Hidrocacbon Ankan Monoxicloankan Anken Ankin Ankadien OximenC) / LimonenC) Cong thfle phan tfl CnH2n+2 CnH2n CnH2n CnH2n-2 '^nH2n^2 CnH2n-2 C10H16 So nguyen tfl H it hon ankan tuong flng 0 2 So' lien ket pi(jt) 0 0 So' vong (v) 0 1 Tong so' (7C +v ) 0 1' (**) Dung ky hieu (n + v) trong cac bai tap se cd Igi va ggn b) Hay cho bid't sd lugng nguydn tfl H d phin tfl xicloankan va b phan tfl mdi loai hidrocacbon khdng no ft hem b phan tfl ankan tuong flng la bao nhieu, giai thfch vi sao lai ft hon ngIn ly . HS thao luln va dua ra ke't qua: l.a) ' ^'-"'v"' Hidrocacbon Ankan Monoxicloankan Anken Ankin Ankadien OximenC) Cong thfle phan tfl CnHan+J CnH2n CnH2„ PnH2h-2 CnH2n-2 CnH2n-2 So nguyen tflH It hon ankan tuong flng 0 2 2 4 4 6 So lien ket pi (t) 0 0 1 2 2 3 So vong (v) 0 1 0 0 0 0 long so (TI + V ) 0 1 1 2 2 3 LimonenC) C10H16 6 2 1 3 0 5-tKBGHHnNCT2 65 b) So nguyen tfl H d xicloankan it hem ankan 2 nguyen tfl vi xicloankan cd 1 vdng no, anken cd sd nguyen tfl H it hom ankan va anken cd 1 lien ket n. Ankin, ankadien cd sd nguyen tfl H ft horn ankan 4 nguyen tfl vi chung cd 2 lien ke't %. GV chieu bai tap 2 (SGK) len man hinh de HS thao luan. 2- Hay dien cac tfl hoac cac sd cho dudi day vao chd trd'ng trong cac cau sau: a) Anken va...(l)...deu cd (TI + y) = 1, nhung...(2)...cd (v) = 1 cdn... (3)...cd(v)=...(4)... b) ...(5)...va...(6)...ddu cd (TI + v) = 2, chung deu cd n =...(7)...va (v>...(8)... A: ankin; B: 1; C: xicloankan; D: 2; E: anken; G: ankadien, H: 2, K: 0 HS thao luan va dua ra ket qua: a) (1) xicloankan (2) xicloankan(3) anken (4) 0 b) (5) ankandien (6) ankin (7)2 (8)0 GV chieu bai tap 3 (SGK) len man hinh de HS thao luan. 3, a) Menton (mui bae ha) cd cdng thfle phan tfl C,oH,gO, chi chfla 1 Uen ke't ddi. Hdi nd cd ca'u tao mach hd hay mach vong? b) Vitamin A cdng thfle phan tfl C20H30O, chi chfla Ivong 6 canh khdng chfla lien ke't ba. Hoi trong phin tfl cd may lien ke't ddi? HS thao luan va dua ra ke't qua: 2 20 + 2 —18 a) Menton cd CTPTC C,oHigO cd TI + v = — = 2(;T + V-2;n = \ va v = l). b) CTPTciia vitamin A la C20H30O cd 2.20 + 2-3 0 , , . , ^s ,,. , .,•«,-', . . .' TI + v= = 6.(71 + v= 6; v=l-> 71= 5), khong co hen ket ba, vay so lien ke't ddi la 5. GV chie'u bai tap 4 (SGK) len man hinh de HS thao luan. 4. a) Hay vie't cdng thfle cl'u tao chung cua anken, ankadien, ankin va neu dac diem trong clu tnic khdng gian cua chung. b) Hay cho bie't nhiing nhdm nguyen tfl nao quye't dinh dac tfnh hoa hgc cua anken, ankadien, ankin. Vi sao ? 66 c) Hay neu nhflng phan flng dac trung cua anken, anka-l,3-dien va ankin. HS thao luan va dua ra ke't qua: a) Cdng thfle chung cua anken, ankadien, ankin. - Anken C„H2„ (n > 2) dac diem cau true khdng gian cac nguyen tfl lien ke't true tiep, vdi C=C ddu nam tren mdt mat phang va gdc lien ke't «120°. - Ankin 0„H2„-2 (" ^ 2) die di^m clu true khdng gian cac nguyen tfl lien ket true tidp vdi CsC ddu nam tren mdt dudng thang va gdc lien ke't bang 180° - Ankadien C„H2„-2 (n > 3) die diem cl'u tnic khdng gian tuy thudc vao vi tf tuong ddi cua cac lidn ke't ddi neu hai ndi ddi each xa nhau thi cae nguyen tfl lien ke't true tie'p vdi C=C deu nam tren mdt mat phang va gdc lien ke't ^HO" b) Nhdm nguyen tfl quye't dinh tfnh chl't cua anken, ankadien, ankin la nhdm: C=C va CsC bdi vi cac nhdni dd cd mang lidn ke't TI kem bdn nen la trung tim cua eac phan flng hoa hgc. c) Phan ling dac trung cua anken, anka-l,3-dien, ankin la phan flng cdng (H2, Br2, HX) phan flng oxi hoa khdng hoan toan. - Ridng ank-l-in cd phan flng the'bdi ion bae tao ra ket tua mau vang. - Anka-l,3-dien ed phan flng cdng 1,2 va cdng 1,4. GV chie'u bai tap 5 (SGK) lenman hinh dd HS thao luan. 5. a) Hay neu nguyen tie chung didu che' anken, ankedien, ankin dd dung trong cdng nghiep tdng hgp hiiu co. Liy vf du didu che' chl't tieu bidu cho mdi loai. b) Vi sao etilen la hoa chit hutx eo dugc san xuat vdi san lugng ldn nhit ? HS thao luln va dua ra ke't qua: a) Nguyen tac chung d^ dieu che' anken, ankadien, ankin la tach hidro ra khdi ankan. Thf du didu che' chit tieu bieu: xem SGK. b) Etilen ngay nay dugc dung lam nguyen lieu quan trgng trong san xul't poUme (PE, PVC--.) va nhidu hoa chl't co ban khac (nhu etanol, axetandehit ...) nen duge san xul't vdi san lugng ldn nhl't. GV chie'u bai tip 6 (SGK) len man hinh di HS thao luln. 6. Diing cdng thfle elu tao hay vidt phucmg trinh hoa hgc cfla phan flng theo so ddsau: +B —* C " C^H^BT^ (mdt cha't) + Br2 "* C4H6Br2 (hai chl't) + AgNOs NH3 E —^—^^ ke't tua 67 HS thao luln va dua ra ket qua: CH3-CH2-CH2-CH3 '°-'" > CH3-CH=CH-CH3 + H2 (A) CH3-CH2-CH2-CH3 '"'^ > CH2=CH-CH2-CH3 + H2 (B) CH3-CH=CH-CH3 '"•" > H2 + CH3-OC-CH3 (C) CH3-CH=CH-CH3 '°-" > H2 + CH2=CH-CH=CH2 (D) CH2=CH-CH2-CH3 ~il=i5-> H2 + CH2=CH-CH=CH2 (D) CH2=CH-CH2-CH3 '"•" ) H2 + CH2SC-CH2-CH3 (E) CH3-OC-CH3 + Br2 -^ CH3-CBr=CBr-CH3 —Cp2-(,^H-CH = CH2 CH,=CH-CH=CH, + Br, Br Br -^C;H2-(;:H-C H = CH2 Br Br HOC-CH2-CH3 + AgN03 + NH3 ^ AgCsC-CH2-CH3 4, + NH4NO3 GV chie'u bai tap 7 (SGK) len man hinh d^ HS thao luln. 7. Khi ddt chay hoan toan mdt hidrocacbon b the khf (dieu kien thudng) thi thiy thd tich cae khf tao thanh sau phan flng dung bang thd tfch cae khf tham gia phan ling (b cung nhiet dd va ap suit). Hay cho bie't hidrocacbon dd cd the nhin nhung cdng thfle phin tfl nhu the' nao ? HS thao luln va dua ra ke't qua: Phuomg trinh hoa hgc. C^Hv+ ( X + ^ ) O2 ^ X CO2 + - H2O V V 1 + X + — = X + — => y = 4 4 2 Vly hidrocacbon b the khf pd the 11: CH4; C2H4; C3H4; C4H4. GV chie'u bai tap 8 (SGK) ldn m,an hinh de HS thao luan. 8. Hdn hgp A gdm hai cha't ke' tiep nhau trong day ddng dang cua etilen. Cho 3,36 lit (dktc) hdn hgp khf tren phan flng hoan toan vdi Br2 trong CCl4'thi thiy khd'i lugng binh chfla nudc brom tang them 7,7 gam. a) Hay xac dinh cdng thfle phan tfl ciia hai anken dd. b) Vie't cdng thfle clu tao cua anken ddng phan cd cung cdng thfle vdi hai anken da cho. 68 HS thao lu$n va dua ra ket qua: Sd mol cua hdn hop A -——= 0,15 (mol) •^ 22,4 Ggi cdng thfle chung cua hai anken la : C-H^^ a) C-H^ +Br2 -^ C-H-Br2 ' n 2n •^ n 2n •' Khd'i lugmg binh brom tang chinh la khd'i lugng cua hai anken. M^=-^ = 5,13 (g/mol) ->14n =51,3=> ii =3,66 0,15 VI hai olefin ke' tiep nhau nen CTPT la : CjHg va C4H8 b) Ggi sd mol eua C3H6: a (mol) ed M= 42 (g/mol); C4H8: b (mol) ed M = 56 (g/mol) ta ed he: | a + b = 0,15 1 42a + 56b = 7,7 Giai he phuong trinh, dugc a = 0,05 ; b = 0,1. % thd tfch C3H, = Mliioo!^ = 33,33% ' 0,15 % the tfch C4H8 = 100% - 33,33% = 66,67% ; c) Cae CTCT cd the cd cua: C3H6 la : CH2 = CH - CH3 C4Hg la : CH2=CH-CH2-CH3; CH3-CH =CH-CH3; CH2 =C-CH3 CH3 GV chie'u bai tap 9 (SGK) len inan hinh dd HS thao luan. 9. Nhiet phan 2,8 1ft (dktc) etan b 1200°C rdi cho mdt nfla hdn hgp khf thu dugc sue qua binh dung nudc brom (du) thi thay khd'i lugng binh nay tang len them l,465g. Cho nfla hdn hgp khf cdn lai phan flng vdi dung dich AgN03 trong amoniac thi thu dugc 0.60g ke't tua mau vang. Bie't rang phan flng nhiet phan taora etilen, axetilen la phan flng khdng hoan toan, eac phan flng tiep sau dd deu xay ra hoan toan. Hay xac dinh thanh phin phin tram ve the tfch cua hdn hgp khf thu dugc. HS thao luln va dua ra ke't qua: 2 8' - Sd mol cua CjHg = - ~ = 0,125 (mol) 69 - Khi nhiet phin QHg thu dugc : C2H4: a (mol); C2H2: b (mol); H2: (a+2b) mol va QHg: du. C2H4 + Br2 -^ C2H4Br2 a a C2H2 + 2Br2 -^ C^H^BT^ b ' 2b C2H2 + 2AgN03 + 2NH3 -^ AgC^CAg 4- + 2NH4NO3 b =^ ^ = 0,005 (mol) do dd: 28a + 26b = 1,465.2 = 2,93 => a = 0,1 (mol) 240 => nH^=a + 2b = 0,l+0,01 =0,11 ^ Uc^H, du = 0,125 - (a + b) = 0,125 - (0,1 + 0,005 ) = 0,01 => Tdng sd mol hdn hgp khi: 0,1 + 0,005 + 0,11 + 0,02 = 0,235 0,1.100% = 42,55% ^o.oos.m% % n c H = ^ — -• ^^"^ 0,235 0,11.100% % n„ = — "^ 0,235 0,235 = 46,8% % n^ „ = 100% - (42,55% + 2,13% + 46,8%) = 8,52% Bai tkp de nghj 1. Ankadien sau ed bao nhidu ddng phin hinh hgc. CH3-CH=CH-CH=CH-CH3 A. 2 B. 3 C. 4 D. Khdng cd ddng phin hinh hgc. Ddp dn B 2. Hdn hgp X gdm hai anken la ddng dang lidn tiep cd ti khd'i so vdi H2 bing 19. Tim cdng thfle phin tfl cac anken va % the tich mdi anken trong hdn hgp. A. C2H4 28,6% va C3H6 71,4%. B. C2H4 71,4% va C3H6 28,6%. C. QHfi 28,6% va C4H8 71,4%. D. CjHg 71,4% va C4Hg 28,6%. Ddp dn A 3. Dot chay hoan toan m gam hdn hgp hai ankin cho ra 13,2 gam CO2 va 3,6 gam H2O. Tinh khd'i lugng brom td'i da eg thd cdng vao m gam hdn hop trdn. A. Khdng du dfl kien B. 32 gam C. 16 gam D. 8 gam 70 4. Khi hidro hoa hoan toan licopen C40H56 thu duge chit C4oHg2 cdn hidro boa hoan toan caroten C40H56 thu dugc chit C4oH7g. Hdi trong licopen va trong caroten ed bao nhieu lien ke't ddi va bao nhieu vdng. Bie't trong phin tfl ca hai chl't chi CO lien ke't dom, lien ket ddi va vdng 6 canh. A. 13 lien ke't ddi, khdng vdng; 11 lidn ket ddi, 2 vdng. B. 11 lidn ke't ddi, khdng vdng; 13 lidn ke't ddi, 1 vdng. C. 12 lidn ke't ddi, 1 vdng; 12 lien ke't ddi, 2 vdng. D. 13 lien ke't ddi, 1 vdng; 13 lien ke't ddi, 2 vdng. Ddp dn A. 5. Ddt chay hoan toan 22,41ft hdn hgp khf X gdm CO, CH4, C3H6 (dktc) thu dugc 44,F 1ft CO2 (dktc). Tfnh % the tfch cua C3H6 trong X. A. 21,9 % B. 25,36 % C. 32,7 % D. 50 % Ddp dn D. 6. Hidrocacbon X tac dung vdi dung dich brom du thu dugc din xul't tetrabrom (chfla 4 nguyen tfl brom) Y. Bie't trong Y brom chie'm 75,82% khd'i lugng. Tim cdng thfle phin tfl cua X. A. C7H10 B. CgHg C. CgHg D. CgHg Ddp dn B. 71 BAI 45 THl/C HANH TINH CHAT CLJA HIDROCACBON KHONG NO A. MUC TIEU BAI HOC 1. Kien thCfc • Bie't dugc muc dich, each tidn hanh, ki thuat tien hanh mdt sd thi nghiem cu the: • Dieu che' va thfl tfnh chit cua axetilen: Phan flng chay, phan flng vdi dung dich brom, vdi dung dich AgN03 trong NH3. • Phan ling cua hidrocacbon khdng no vdi nudc brom. • Cung cd tfnh chit If hoa cua mot so hgp cha't hihi co nhu tecpen, axetilen. 2. KTnang • Sfl dung dung cu, hoa chit de tie'n hanh dugc an toan, thanh cdng cac thf nghiem tren. • Quan sat, md ta hien tugng, giai thfch, viet cac phuomg trinh boa hgc. • Viet tudng trinh thf nghiem. 3. TTnh cam, thai do • Bie't each dieu che tfl dd sfl dung hgp If hoa chit lugng nhd. • Thdng qua boat ddng thi nghidm tao nen hflng thu khi hgc bd mdn hoa hgc. B. CHUAN B! CUA GV VA HS • GV -May tinh, may chie'u, hinh ve. - Hoa cha't: + Dl't den. + Nudc cl't. + Nude brom. + Ca chua chin. + Dung dich KMn04. + Dung dich AgN03/NH3. - Dung cu: + Ong nghiem , den cdn. + Ong hut nhd gigt. + Nut cao su cd lip d'ng thuy tinh vudt nhgn. 72 • HS: + Bd gia thf nghiem. + Coi gia, cdc thf nghiem. - On tap kie'n thfle cua hidrocacbon khdng no. - Xem trudc bai thuc hanh. C. TIEN TRINH DAY- HOC Hoat ddng cua GV Hoat ddng ciia HS Hoat dong 1 Dan dd trudc buoi thUc hdnh GV neu cac ndi dung chfnh cua budi thuc hanh. GV yeu clu HS trinh bay cac kien thfle lien quan den budi thue hanh. - Luu y HS khi dung hoa chl't va sfl dung cin thin cac dung cu thf nghiem. - Chia ldp hgc thanh cae nhdm thuc hanh mdi nhdm gdm 4-5 HS. HS nghe GV trinh bay va thao luan theo nhdm thuc hanh. I. NOI DUNG THI NGHIEM VA CACH TIEN HANH Hogt dong 2 Thi nghiem 1. Dieu chevd thvc tinh chdt ciia etilen Hoqt dong 3 Thi nghiem 2. Dieu chevd thu: tinh chdt ciia axetilen GV: Hudng din HS cac nhdm lam thf nghiem nhu SGK. GV yeu clu HS quan sat hien ti^gng va HS lam thf nghiem theo cae budc: - Cho m.dt vai miu CaQ bang hat dd den vao mdt d'ng nghiem to duge kep chat trdn gia sit. - Rdt nude vao dng nghiem, dly nhanh bang nut cao su cd elm d'ng din khi. HS quan sat thiy cd khi khdng mau thoat ra manh liet. 73 giai thich. GV yeu clu HS thfl nidt sd tfnh chl't vlt If cua khf thoat ra: - Tfnh tan (trong nude). -Mui . GV yeu cau HS giai thfch: - Tai sao khi thoat ra cd mui ma theo tinh chl't cua axetilen la khdng cd mui. - Cach loai trfl die khi dd. GV chie'u len man hinh md hinh mdt so dung cu dieu che' axetilert: GV hudmg din HS tiep tuc thfl cac tfnh chat hoa hgc cua axetilen. GV yeu clu HS nhdm 1 lam thf nghiem dot chay khf C2H2 thoat ra. GV luu y HS: Axetilen chay toa nhieu nhiet nen phai lam thf nghiem vdi lugng nhd boa chl't va can thin khi dd't khf. 74 Giai thfch: Do cd phan ung hoa hgc sau xay ra. CaC2+ 2H2O -> Ca(OH)2 + C2H2t HS tien hanh thfl tfnh chit vat If: - Sue khf thoat ra vao nudc tha'y khf thoat ra hlu nhu khdng tan trong nude. - Dung tay vay nhe khf thoat ra ngfli tha'y khi cd mui khd chiu (mui khi dat den). HS thao luan: - Khi axetilen khdng cd mui, nhung lai lin mdt sd tap chit sinh ra nhu H2S, NH3, cd trong dit den (CaC2). - De loai trfl khi H2S va NH3 ta cho khi di qua dung dich NaOH loang. HS tidp tuc lam thi nghiem thfl tinh chit: Thi nghiem dot ehay C2H2: + Cho mdt vai miu CaCj bang hat dd den vao mdt d'ng nghiem to dugc kep chat tren gia sat. + Rdt nude vao d'ng nghiem. + Dly nhanh bang nut cao su cd elm d'ng din khi. + Dd't khf thoat ra ya dfla mat sfl trlng lai gin nggn Ifla. - Hien tugng: Axetilen chay vdi nggn Ifla sang, toa nhidu nhiet, tao ra CO2 ,va nudc, khi dua mat sfl trlng lai gin xul't hien mudi den va cac gigt nudc tren mat sfl. GV ydu clu HS nhdm 3 lam thf nghiem sue khf qua dung dich brom va dung dich KMn04. GV gidi thieu: phuong trinh boa hgc cua C2H2 vdi KMn04 (dly la phan flng pha vo lidn ke't ba tao ra cac san ph^m phfle tap): 3C2H2 + 8KMn04 -^ 3(COOK)2 + 8Mn02>l' +KOH + H2O GV yeu clu HS nhdm 3 lam thf nghiem sue khf thoat ra vao dung dich AgN03 trong dung dich NH3. Yeu clu HS quan sat, cfl tflng nhdm HS mo ta hien tugng thf nghiem va giii thfch bang phucmg trinh hoa hgc. Giai thfch: do cd phan flng hoa hgc: 5 QH2+^0 2 -> 2CO2 + H2O (AH < 0) Ngoai ra cd mdt phin C2H2 chay khdng hoan toan sinh ra C nen lam den mat sfl va hoi nude'ngung tu tao thanh gigt tren mat sfl. HS tien hanh thf nghiem. Thf nghiem phan flng vdi nudc brom va dung dich KMn04. HS: Sue tfl tfl khf C2H2 dieu che' nhu thf nghiem tren vao vao nudc brom thiy nudc brom bi nhat mau din, khi sue vao dung dich KMn04 thi thiy mau tim cua dung dich nhat din ddng thdi cd xult hien ke't tua mau nlu. Giai thfch: do cd phan flng hoa hgc: C2H2 + Br2 —^ C2H2Br2 1,2-dibrometen C2H2Br2 + Br2 -^ C2H2Br4 1,1,2,2-tetrabrometan HS nhdm 3 tie'n hanh thi nghiem phan flng cua C2H2 vdi dung dich AgN03/NH3. - Din ddng khi qua cac dng nghiern dung dung dich AgNOj/NHj (da chuan bi san). - Hien tugng thiy cd kd't tua mau vang xult hien. - Giai thfch: Do C2H2 phan flng vdi dung dich AgN03/NH3 tao ra ke't tua mau vang (bae axetilua). HC=CH + 2AgN03 +2NH3 -^ AgC=CAg + 2NH4NO3 75 Hoqt dqng 4 Thi nghiem 3. phdn Ung cua hidrocacbon khong no vdi nudc brom GV hudng nghiem. din HS tie'n hanh thi HS tie'n hanh thi nghiem: - Cho vai gigt diu thdng vao dng nghidm chfla 2ml nudc brom, lac Id, de yen vai phiit. - Hien tugng thiy nude brom bi nhat Yeu clu HS quan sat, neu hien tugng va giai thfch. (GV hudng din HS phin tfch thanh phin cua diu thdng de giai thfch hien tuong thi nghiem). mau, ne'u de llu thi se mlt mau. - Giai thich: Diu thdng la mdt tecpen cd trong thien nhien (a-pinen CioHig); Khi phan flng boa hgc xay ra cgng brom vao ndi ddi cua tecpen cd trong diu tao thanh din xul't di halogen khdng mau. > GV hudng nghiem. din HS tie'n hanh thf HS tie'n hanh thi nghiem: - Cat ddi qua ca chua chin tach bd cac hat ra. - Nghien nat phin ca chua da bd hat, Igc liy phin nudc thu dugc nudc ca chua ed mau do. - Nhd tfl tfl tflng gigt nude brom (mau GV yeu clu HS giai thich hien tugng. GV ghi nhin cac y kien va bd sung each giai thich dly du ngln ggn; - Nudc ca chua chin ep eung la mot tecpen (licopen C4oH5g) trong phin tfl cd nhieu lien ke't ddi lien hgp. - Khi phan flng hoa hgc xay ra, Br2 cdng vao mdt so ndi ddi din de'n so ndi ddi lien hgp thay ddi va ke't qua mau sac thay ddi theo. - Ngoai tecpen trong nudc ca chua cdn cd mot so hgp chit khac anh hudng den mau cua dung dich. 76 nau nhat) vao nude ca chua (mau do), lac kl, de ydn thiy hien tugng dung dich chuyen sang mau tim nhat. - Tie'p tuc nhd vai gigt; brom vao lac kl, dd yen thiy dung dich chuyan sang mau xanh nhat. Hoqt dqng 5 II. CONG VIEC SAU BUOI THLTC HANH GV: Nhin xet vd budi thue hanh va hudng din HS thu dgn hoa chit, rfla d'ng nghiem va dung cu thi nghiem, ve sinh phdng thf nghiem. GV: Yeu clu HS lam tudng trinh theo miu. HS: thu dgn, ve sinh phdng thi nghiem cin than, an loan. HS lam tudng trinh theo miu sau day: Ngay thang nam Hg va ten:......... Ldp: Td thf nghiem: Tudng trinh hoa hgc bai so: Ten bai: Ten thi nghiem Phuong phap tien hanh Hien tugng quan sat Giai thich - vie't phuang trinh phan flng 77 ChMnq VII HKmOCACBON THdM NCU6N HHNIOCACBON THIEN NHIEN BAI 46 BENZEN VA ANKYLBENZEN A. MUC TIEU BAI HOC l.KlenthiJc HSbiet: • Dinh nghia, cdng thfle chung, die diem cl'u tao, ddng phin, danh phap. • Tfnh chat vlt If: Quy lull bie'n ddi nhiet do ndng chay, rthiet dd sdi cua cac cha't trong day ddng dang benzen. • Tinh chit hoa hgc: Phan ung the' (quy tie the"), phan flng cdng vao vdng benzen. Phan flng the' va oxi hoa mach nhanh. HS hieu: • Ca'u tao dac biet cua vdng benzen: ca'u true phang va phan tfl cd dang hinh luc giac deu, cd he lien ket TT lien hop la nguyen nhan din den benzen the hien tfnh chit cua hidrocacbon no va khdng no. 2. KT nang • Vidt duge cdng thfle clu tao cua benzen va mdt sd chit trong day ddng dang. • Viet dugc cac phuomg trinh hoa hgc bidu didn tfnh chl't hoa hgc ciia benzen va mdt sd chl't trong day ddng dang, vin dung quy tie the' di du doan san pham cua phan flng. • Tfnh khd'i lugng benzen, toluen tham gia phan flng hole thanh phin phin tram ve khd'i lugng cua chl't trong hdn hgp. 3. Tinti cam, thai do Hidu dugc each giai quye't mau thuin gifla clu tao va tinh cha't hoa hoc cua hidrocacbon thom tao nen su hflng thu khi giai quye't vlh de mdi. 78 """