Gio khoa ha hu c 28 n: V Hng Thi Chng trnh Ha hc III. ANKEN (ALCEN, OLEFIN, DNG NG ETILEN, ) III.1.

nh ngha Anken l mt loi hirocacbon m trong phn t c cha mt lin kt i C=C mch h. III.2. Cng thc tng qut CnH2n (n 2) III.3. Cch gi tn Ankan Anken ( C thm s ch v tr ca lin kt i, t pha sau hoc pha trc, c nh s nh. Mch chnh l mch cha ni i v di nht) (Nh trn) Eten ; Etilen Propen ; Propilen 1- Buten ; Buten - 1 ; n- Butilen 2 - Buten ; Buten - 2 ; 2 - Butilen 2 - Metylpropan ; Isobutilen

Bin so

Ankan Ankilen Th d: CH2=CH2 (C2H4) 4 1 CH3-CH=CH2 (C3H6) 2 1 CH3-CH2-CH=CH2 (C4H8) 2 3 4 CH3-CH=CH-CH3 (C4H8) 1 2 3 CH3-C=CH2 (C4H8) CH3 3 5 4 3 2 1 CH3-CH2-CH2-CH=CH2 (C5H10) 2 3 4 5 CH3-CH=CH-CH-CH3 (C6H12) CH3 CH3 6 5 4 3 CH3-CH-CH2-C- CH2-CH2-CH3 2 1 Bin so 29 n: V Hng Thi 5 CH3 4 3 2 1

1 - Penten ; Penten - 1 ; n- Amylen 4-Metyl-2-penten; 4-Metylpenten-2

(C11H22) CH3

3,5-imetyl-3-n-propyl hexen-1 CH=CH2Gio khoa ha hu c

CH3-CH-CH = C-CH-CH3 2,5-imetyl-3-clohepten-3 6 7 CH2-CH3 Cl Ghi ch G.1. Lin kt (sigma, xch ma) l mt loi lin kt cng ha tr, c to ra do s xen ph dc theo trc i xng ca cc obitan (orbital, vn o) nguyn t to lin kt. Vi hai obitan nguyn t khi xen ph dc theo trc i xng to lin kt th hai trc i xng ca hai obitan ny trng lp ln nhau (chng ln nhau). Th d: H + H H H H H (H2) Hai obitan s hnh cu ca hai nguyn t H trc khi xen ph to lin kt Xen ph dc trc i xng Lin kt s-s

Cl

Cl

Cl Cl Xen ph dc trc i xng H Cl

Cl Cl

(Cl2) Lin kt p-p

Hai obitan p hnh s 8 cn i ca ca hai nguyn t Clo H + Cl

H Cl

(HCl)

Obitan s hnh cu Obitan p hnh s 8 Xen ph dc trc Lin kt s-p ca H ca Cl i xng G.2. Lin kt (pi) l mt loi lin kt cng ha tr, c to ra do s xen ph bn ca cc obitan nguyn t to lin kt. Vi hai obitan nguyn t p khi xen ph bn to lin kt th hai trc i xng ca hai obitan nguyn t ny song song vi nhau v cng thng gc vi trc ni hai nhn nguyn t (trc lin nhn). Gio khoa ha hu c Bin so 30 n: V Hng Thi Xen ph bn, hai trc i xng song song v cng thng gc vi trc ni hai nhn G.3. Mt lin kt n cng ha tr gm mt lin kt . G.4. Mt lin kt i cng ha tr gm mt lin kt v mt lin kt . G.5. Mt lin kt ba cng ha tr gm mt lin kt v hai lin kt . Th d: C C C=C CC 2 C H C O C=O NN 2 Hai obitan p, c hai trc i xng song song Lin kt p-p

G.6. Lin kt km bn hn lin kt v in t trong lin kt cng linh ng hn so vi in t trong lin kt . in t c th di chuyn trn nhiu nguyn t trong phn t , cn in t ch di chuyn trong vng khng gian bao quanh hai nguyn t to lin kt. G.7. C s quay t do quanh mt lin kt n, nhng khng c s quay t do quanh mt lin kt i cng nh mt lin kt ba cng ha tr. V khi quay nh vy th lin kt c trong lin kt i, lin kt ba s b ph v. Th d: C C C O C C C C C O G.8. di lin kt n di hn di lin kt i, di lin kt i di hn di lin kt ba. Th d: d C-C (1,54 A 0 ) > d C=C (1,34 A 0 ) > d CC (1,20 A 0 ) Gio khoa ha hu c 31 n: V Hng Thi G.9. iu kin mt cht c ng phn cis, trans (ng phn Z, E; ng phn hnh hc; ng phn khng gian; ng phn lp th) l: + Phn t cht phi c cha t nht mt lin kt i C=C + V mi cacbon ni i phi lin kt vi hai nguyn t hay hai nhm nguyn t khc nhau. Hai nguyn t hay hai nhm nguyn t tng ng lin kt vo hai nguyn t cacbon ni i nu nm cng mt bn mt phng ni i (mt phng ) th c ng phn cis (Z), nu hai nguyn t hay hai nhm nguyn t tng ng ny nm hai bn mt phng ni i th c ng phn trans (E). Hin nay, ngi ta dng cis-trans ch hai nhm th ging nhau cng mt bn hay hai bn mt phng ni i, cn dng Z-E ch hai nhm th c cng mc u tin cng mt bn hay hai bn mt phng ni i. A A A B C=C C=C B B B A Cis Trans AB A B A A ( A tng ng A, A c th l A) B B ( B tng ng B, B c th l B) Nguyn nhn ca ng phn cis-trans l do khng c s quay t do quanh lin kt i C=C, nn hai cu to cis, trans hon ton khc nhau. Th d: CH2=CH2 (Etilen) khng c ng phn cis, trans CH3-CH=CH2 (Propilen) khng c ng phn cis, trans CH2=CH-CH2-CH3 (1- Buten; Buten-1) khng c ng phn cis, trans CH3-C=CH2 (Isobutilen) khng c ng phn cis, trans

Bin so

CH3 Buten-2 c ng phn cis, trans: H 1 2 3 4 CH3-CH=CH-CH3 2-Buten (Buten-2) Bin so 32 n: V Hng Thi CH3 H 6 5 4 3 2 1 CH3-CH2-C=CH-CH-CH3 (2,4-imetylhexen-3) c ng phn cis-trans CH3 CH3 CH3-CH2 H C=C Trans CH3 CH(CH3)2 CH3-CH2 CH(CH3)2 C=C CH3 H Bi tp 19 Vit CTCT cc ng phn cis- trans, nu c, ca cc cht sau y: a. Stiren (C6H5-CH=CH2) b. 1,2-icloeten (Cl-CH=CH-Cl) c. HOOC-CH=CH-COOH d. Axit metacrilic [ CH2=C(CH3)COOH ] e. Hexen-2 f. 2,4-imetylhexen-3 Bi tp 19 Vit CTCT cc ng phn cis-trans (nu c) ca cc cht sau y: a. Axit xinamic (C6H5-CH=CH-COOH) b. Axit acrilic ( CH2=CH-COOH ) c. Crotonanehit ( CH3-CH=CH-CHO ) d. Nitrinacrilic ( CH2=CH-CN) e. Benzanaxetophenon (C6H5-CH=CH-CO-C6H5) f. 3,4-imetylhexen-2 III.4. Tnh cht ha hc III.4.1. Phn ng chy CnH2n 0 nCO2 + nH2O Anken (Olefin) n mol n mol + 3n/2 O2 t Cis H Cis-2-buten C=C CH3 CH3 H CH3 C=C

Trans-2-buten Gio khoa ha hu c

Lu Khi t chy anken thu c s mol nc bng s mol CO2 , hay th tch hi nc bng th tch kh CO2 (trong cng iu kin v nhit v p sut). III.4.2. Phn ng cng Hiro (Phn ng hio- ha) Phn ng cng l phn ng trong phn t mt cht nhn thm vo phn t ca n mt hay mt s phn t khc to thnh mt phn t sn phm. iu kin mt cht cho c phn ng cng l phn t cht ny phi c cha lin kt hoc vng nh ] Gio khoa ha hu Bin so 33 n: V Hng Thi CnH2n + H2 Ni (Pt), t 0 CnH2n +2 Anken Hiro Ankan Olefin Parafin Th d: -2 -2 0 -3 +1 -3 +1 CH2=CH2 + H2 Ni t 0 CH3-CH3 (C2H4) (C2H6) Etilen Etan (Cht oxi ha) (Cht kh) -1 -2 0 -2 +1 -3 +1 CH3-CH=CH2 + H2 Ni t 0 CH3-CH2-CH3 (C3H6) (C3H8) Propen, Propilen Hiro Propan (Cht oxi ha) (Cht kh) Lu L.1. Trong phn ng anken cng H2, th H2 ng vai tr cht kh, cn anken ng vai tr cht oxi ha. Do ngi ta cn ni dng H2 kh anken nhm to ankan hay anken b kh bi H2 to ankan. L.2. anken cng hiro th cn dng cht xc tc v nhit thch hp. Nu thiu mt trong hai iu kin ny th c th phn ng khng xy ra. L.3. Phn ng cng H2 vo anken thng xy ra khng hon ton. Ngha l sau phn ng, ngoi sn phm ankan, c th cn c hai tc cht l anken v H2. Ch khi no gi thit cho phn ng xy ra hon ton hay hiu sut 100% v c H2 d hay va th tt c lng anken c lc u mi phn ht to ankan. Bi tp 20 Hn hp kh A gm 0,5 mol etilen v 22,4 lt H2 (ktc) c cho vo mt bnh kn c cha mt t bt Ni lm xc tc. un nng bnh mt thi gian, thu c hn hp kh B. a. Hn hp B c th gm cc cht no? Tnh khi lng hn hp B. b. Bit rng trong hn hp B trn c cha 2,8g mt cht X m khi t chy to s mol nc bng s mol CO2. Tnh % th tch mi kh trong hn hp B v tnh hiu sut

phn ng gia etilen vi hiro. (C = 12 ; H = 1) S: a. 16g b. 36,36% C2H6 9,09% C2H4 54,55% H2 ; 80% Bi tp 20 Hn hp kh X gm 0,3 mol propilen v 3,52 lt H2 (27,3 0 C, 1,4 atm) c cho vo mt bnh kn c cha mt t bt Ni lm xc tc. un nng bnh mt thi gian, thu c hn hp kh Y. a. Hn hp Y c th gm cc cht no? Tnh khi lng hn hp Y. b. Cho bit trong hn hp Y trn c cha 6,6 gam cht Z, m khi t chy Z th thu c s mol CO2 nh hn s mol H2O. Gio khoa Bin so 34 n: V Hng Thi Tnh % th tch mi kh trong hn hp Y v tnh hiu sut phn ng propilen cng H2. (C = 12 ; H = 1) S: a. 13g b. 42,86% C3H8 42,86% C3H6 14,28%H2 ; 75% III.4.3. Phn ng cng halogen X2 (Ch yu l cng brom, Br2) + Th d: CH2=CH2 + (C2H4) Eten, Etilen CH3-CH=CH2 (C3H6) Propen, Propilen CnH2n X2 Anken CnH2nX2 Halogen Br2

ha

hu

Dn xut ihalogen ca ankan

CH2-CH2 Br Br (C2H4Br2) Nc brom 1,2-ibrometan, Etylenbromua + Br2 CH3-CHBr-CH2Br (C3H6Br2) Nc brom 1,2-ibrompropan, Propylenbromua

Lu L.1. Anken cng brom d dng. Ch cn dung dch brom, khng cn brom nguyn cht, v phn ng xy ra c ngay c trong bng ti. Do phn ng cng brom vo anken xy ra hon ton, c brom d th ht anken hoc ngc li. L.2. Cc anken lm mt mu nc brom d dng, iu ny cng ng vi cc hp cht khng no ni chung (c lin kt i C=C, lin kt ba CC trong phn t), v c phn ng cng brom vo lin kt i, lin kt ba gia C vi C. Ngi ta thng vn dng tnh cht ha hc ny nhn bit anken, cng nh cc hp cht khng no ni chung. Bi tp 21 Mt hirocacbon X khi cho tc dng vi clo to nn mt dn xut clo Y Nu ha hi Y th thu c mt th tch bng 9 4

th tch kh CO2 c khi lng tng ng trong cng iu kin. a. Xc nh cng thc ca X. b. Nu X tc dng vi clo theo ch to cht Y duy nht, xc nh CTCT ca X. c. Phn bit cc cht: metan, X, CO2, N2 v H2, ng trong cc l khng nhn. (C = 12 ; H = 1 ; O = 16 ; Cl = 35,5) S: a. C2H6 hay C2H4 b. CH2=CH2 Bi tp 21 A l mt hirocacbon. A tc dng Br2 to sn phm l mt dn xut brom B. Nu cho B ha hi th thy mt th tch etan bng 7,2 th tch hi B tng ng khi lng (trong cng iu kin v nhit v p sut). a. Xc nh CTPT c th c ca A. Vit cc phn ng xy ra. Gio khoa ha hu c Bin so 35 n: V Hng Thi b. Nu A tc dng brom ch to mt sn phm duy nht l B. Xc nh CTCT ca A. c tn A. Bit rng A l ng phn hnh hc ca A (A dng cis).Vit phn ng xy ra. (C = 12 ; H = 1 ; Br = 80) S: a. C4H8, C4H10 b. A: CH3-CH=CH-CH3 (trans) Bi tp 22 Hn hp kh A gm etilen v hiro. Cho 6 gam hn hp A vo mt bnh kn c cha mt t bt Ni lm xc tc. un nng bnh mt thi gian, thu c hn hp kh B. Dn hn hp B qua bnh ng nc brom c d, c 4,48 lt hn hp kh C (ktc) thot ra v khi lng bnh brom tng thm m gam. T khi hi ca C so vi hiro bng 11,5. a. Tnh m. b. Tnh % khi lng mi kh trong hn hp B v tnh hiu sut phn ng cng hiro ca etilen. (C = 12 ; H = 1) S: a. m = 1,4g b. 75% C2H6 ; 23,33% C2H4 ; 1,67% H2 HS = 75% Bi tp 22 Hn hp kh X gm propilen v H2. Cho 6,5 gam hn hp X vo mt bnh kn, c cha mt t bt niken lm xc tc. un nng bnh mt thi gian, thu c hn hp kh Y. Dn hn hp Y qua bnh ng dung dch brom d, khi lng bnh brom tng thm m gam v c 1,76 lt hn hp kh Z (27,3 0 C; 1,4 atm). dZ/metan = 2,225. a. Tnh m. b. Tnh hiu sut phn ng cng gia propilen vi hiro. (C = 12 ; H = 1) S: a. m = 2,94 gam b. HS = 80% III.4.4. Phn ng cng nc (Phn ng hirat ha) CnH2n + H2O H3PO4 t 0 ,p CnH2n + 1OH

Anken (Olefin) (l), t 0 ] Th d:

Nc

[ H2SO4

Ru n chc no mch h CH2=CH2 (C2H4) + H2O H3PO4 280 - 300 CH3-CH2-OH

0 C , 70 - 80 atm Etilen

(C2H5OH) Etanol , Ru etylic CH3-CH-CH3 OH + H2O H3PO4

CH3-CH=CH2 ,t 0 ,p

(Sn phm chnh) Propen , Propilen

Nc CH3-CH2-CH2-OH (Sn phm ph) Markovnikov Gio khoa ha c

Ghi ch: Qui tc hu Bin so 36 n: V Hng Thi Khi cng mt tc nhn bt i xng vo mt anken bt i xng th sn phm chnh c to ra l do phn ion dng ca tc nhn lin kt vo cacbon ni i mang nhiu H hn, phn ion m ca tc nhn lin kt vo cacbon ni i t H hn. Sn phm ph th ngc li. Th d: OH CH3-CH2-C-CH3 CH3 CH3-CH=C-CH3 + H2O H3PO4 ,t 0 ,p (Sn phm chnh) CH3 Nc Ru tert-pentylic 2-Metyl-2-buten CH3-CH-CH-CH3 OH CH3 3-metyl-2-butanol ( Sn phm ph ) OH CH3-C-CH3 CH3 CH3-C=CH2 ,t 0 + H2O H3PO4

,p

(Sn phm chnh) CH3 Isobutilen

Nc

Ru tert butylic CH3-CH-CH2-OH CH3 (Sn phm ph) Ru isobutylic

III.4.5. Phn ng cng HX (HF, HCl, HBr, HI) CnH2n + HX t o , xt CnH2n + 1X Anken Hirohalogenua Th d: CH2=CH2 o , xt CH3-CH2-Cl Etilen 2-Clo Propan + HCl t

Dn xut monohalogen ca ankan

Hiroclorua

Clo etan Etyl clorua CH3 Cl Isopropyl Clorua

- CH - CH3 0 , xt

CH3-CH=CH2

HCl

(Sn phm chnh) Propen, propilen Hiro clorua CH3- CH2- CH2- Cl (Sn phm ph) 1-Clopropan, n-propyl clorua Br CH3- C- CH3 CH3Gio khoa ha hu c

Bin so 37 n: V Hng Thi CH3-C=CH2 + HBr t 0 , xt (Sn phm chnh) CH3 Hirobromua Isobutilen CH3- CH- CH2- Br CH3 (Sn phm ph) III.4.6. Phn ng trng hp Phn ng trng hp l phn ng trong cc phn t ca cng mt cht kt hp li

to thnh cht c khi lng phn t ln hn. Cht c khi lng phn t ln c lp i lp li bi cc n v mt xch ging nhau. nA ( , ) 0 TH t Xt (A) n n: h s trng hp Anken thuc loi hirocacbon khng no, phn t c cha lin kt i C=C (1, 1) nn gia cc phn t ca cng mt anken c th cng vi nhau c, tc anken cho c phn ng trng hp. xxn TH nCx Hx (C H ) 2 2 Th d:

Anken

Polime ca anken

n CH2=CH2 ( , ) 0 TH t Xt (-CH2-CH2-)n Etilen n CH3-CH=CH2 (

Polietilen Nha P.E

, ) 0 TH t Xt - CH - CH2-

Propilen

CH3 n Polipropilen, nha PP

Bi tp 23 Vit cc phn ng trng hp c th c ca C5H10. c tn tc cht, sn phm thu c. S: 5 phn ng Bi tp 23 Vit cc phn ng trng hp c th c ca C4H8. c tn cc tc cht v sn phm. S: 3 phn ng

III.4.7. Phn ng b oxi ha bi dung dch KMnO4 (Kali pemanganat, thuc tm) -1 -1 +7 0 0 +4 3 R-CH=CH-R + 2 KMnO4 + 4 H2O 3 R-CH - CH-R + 2 MnO2 + 2 KOH OH OH Anken Kali pemanganat Ru a chc Mangan ioxit (cht kh ) (cht oxi ha) (kt ta mu en) Gio khoa ha hu c Bin so 38 n: V Hng Thi 3 CnH2n + 2 KMnO4 + 4 H2O 3 CnH2n(OH)2 + 2 MnO2 + 2 KOH Anken Kali pemanganat Ru a chc Mangan ioxit Th d: -2 -2 +7 3 CH2=CH2 + 2 KMnO4 + 4 H2O - CH2 + 2 MnO2 + 2 KOH Etilen Kali pemanganat (Cht kh) (Cht oxi ha) -1 -2 +7 3 CH3-CH=CH2 + 2 KMnO4 + 4 H2O Propilen -1 -1 +7 3CH3-CH=CH-CH3 +2KMnO4 + 4H2O Buten-2 (Cht kh) (Cht oxi ha) -1 3 CH2 Mangan ioxit 0 -1 3 CH3- CH - CH2 + 2 MnO2 + 2 KOH OH OH Propylenglicol 0 0 3CH3-CH-CH-CH3 +2MnO2 +2KOH OH OH 1,3-Butaniol OH OH Etilenglicol -1 +4

+4

+4

Cc anken lm mt mu tm ca dung dch KMnO4 l do c phn ng oxi ha-kh trn, nn dung dch KMnO4 cng thng c dng nhn bit cc anken (cng nh cc hp cht khng no khc). III.5. ng dng III.5.1. T anken iu ch c polime tng ng (Thc hin phn ng trng hp) Th d: n CH2 = CH2 Trng hp (- CH2 - CH2 -)n Etilen (t 0 , xt) Polietilen (Nha PE) III.5.2. T anken iu ch c ru n chc no mch h, ru nh chc no mch h CnH2n 0 ,p + H2O H3PO4 t

CnH2n + 1OH

Anken CnH2n Anken CnH2nBr2 0 +

Nc Br2 Nc brom + 2NaOH

Ru n chc no mch h (Ankanol) CnH2nBr2 Dn xut ibrom ca ankan t Ru nh chc no mch hGio khoa ha Bin so

CnH2n(OH)2 Dn xut ibrom ca ankan Dung dch xt hu c 39 n: V Hng Thi Th d: CH2=CH2 + H2O H3PO4 , 280- 300 0 C , 70- 80 atm CH3-CH2-OH Etilen Nc CH3-CH=CH2 - CH-CH2 Propen, Propilen CH3-CH-CH2 0 + + Br2 Nc brom 2NaOH t CH3

Ru etylic

Br Br 1,2-Dibrompropan, Propylen bromua

OH OH Dung dch xt 1,2-Propaniol , Propylenbromua (Hoc cho anken CnH2n tc dng trc tip vi dung dch KMnO4 ta cng thu c ru nh chc no mch h CnH2n(OH)2 nh bit III.4.7) III.5.3. T anken iu ch c ankan tng ng CnH2n + H2 Ni , t 0 CnH2n + n Anken , Olefin Hiroo Ankan , Parafin Th d: CH2=CH2 + H2 Ni , t 0 CH3-CH3 Etilen Hiro Etan CH3-CH=CH-CH3 0 CH3-CH2-CH2-CH3 2-Buten III.5.4. T etilen iu ch c ru etylic, anehit axetic, axit axetic, este etylaxetat, ietyl ete n-Butan + H2 Ni , t

CH3-CH-CH2 Br Br

CH2=CH2 + H2O H3PO4 , 280-300 0 C , 70-80atm CH3-CH2-OH Etilen Nc CH3-CH2-OH 0 CH3-CHO + Cu Ru etylic CH3-CHO 2 1 O 2+ CH3 C O OH + CH3 CH2 OH CH3 C O O CH3 + H2O CH2 Axit axetic Ruou etylic Etylaxetat Nuoc H2SO4 t 0Gio khoa ha hu c 40 n: V Hng Thi Mn CH3-COOH Oxi Axit axetic + + H2O ng (II) oxit 2 Anehit axetic + CuO t

Ru etylic

ng

Nc

Bin so

III.5.5. Kh etilen cn c dng gi tri cy cho mau chn. V etilen c tc dng kch thch s hot ng cc men lm tri cy mau chn. III.6. iu ch anken III.6.1. ehirat- ha (tch nc, loi nc) ru n chc no mch h, thu c anken (olefin) CnH2n + 1OH H2SO4 () , 180 0 CnH2n + H2O Ru n chc no mch h (n 2) Anken, Olefin

Nc

Th d: CH3-CH2-OH 0 CH2=CH2 Etanol 0 Propen, propilen Lu L1. Ru no m sau khi ehirat ha thu c anken hay olefin th l ru n chc no mch h v phn t c cha s nguyn t C 2. Ru ny c cng thc tng qut l CnH2n + 1OH vi n 2. L.2. Qui tc Zaitsev: 2 CH3 CH2 OH CH3 CH2 O CH2 CH3 + H2O Etanol Dietyl ete Nuoc H2SO4 140 0 CH3 CH2 CH OH CH3 CH3 CH CH CH3 + H2O 2 Buten Nuoc (san pham chinh) CH3 CH2 CH CH2 + H2O 1 Buten (san pham phu) 2 Ruou sec butylic Butanol CH3 CH OH CH3 H2SO4 (d) 180 CH3-CH=CH2 + H2O Ru n- propylic + H2O Eten, Etilen H2SO4 () , 180 Nc H2SO4 () , 180

CH3-CH2-CH2-OH

0 CH3 CH CH2 + H2O Ruou isopropylic, 2 Propanol Propen, propylen NuocGio khoa ha Bin so 41 n: V Hng Thi Khi mt ru n chc no mch loi nc thu c hai anken khc nhau, th anken to ra nhiu hn (sn phm chnh) l ng vi mt H C c bc cao hn. Cn anken to ra t hn (sn phm ph) l ng vi s mt H C c bc thp hn. (Hay sn phm chnh ng vi anken c mang nhiu nhm th hn, hay ng vi anken c cha nhiu H hn). Th d: CH3-CH2-CH=C- CH3 + H2O II III CH3 CH3-CH2-CH-CH-CH3 H2SO4 () (8 H; 3 nhm th) OH CH3 180 oC (Sn phm chnh) CH3-CH=CH-CH-CH3 + H2O CH3 (4 H; 2 nhm th) (Sn phm ph) CH3-CH2-CH=CH-CH3 + H2O (5 H; 2 nhm th)

hu

II I CH3-CH2-CH2-CH-CH3 H2SO4 () (Sn phm chnh) OH 180 oC

II II CH3-CH2-CH-CH2-CH2-CH3 H2SO4 () OH 180 oC

CH3-CH2-CH2-CH=CH2 + H2O (2 H; 1 nhm th) (Sn phm ph) CH3-CH=CH-CH2-CH2-CH3 + H2O (5 H; Sn phm chnh)

CH3-CH2-CH=CH-CH2-CH3 + H2O (4 H; Sn phm ph) III III CH3-CH -CH2-CH-CH2-CH3 H2SO4 () (7 H; Sn phm chnh) CH3 OH CH3 180 oC CH3-C=CH-CH-CH2-CH3 CH3 CH3 + H2O

CH3-CH-CH=C-CH2-CH3 + H2O CH3 CH3 (6 H; Sn phm ph) Gio khoa ha hu c Bin so 42 n: V Hng Thi III.6.2. T Ankan iu ch Anken (thc hin phn ng cracking) 2 2 ' 2 ' 2 ' 2( ') (,,) nno Cn Hn Cn n Hnn t p xt cracking CH++ + Ankan Parafin Th d: CH3-CH2-CH3 Propan CH3-CH2-CH2-CH3 n- Butan cracking Cracking CH4 + CH2=CH2 Metan tilen CH4 + CH2=CH-CH3 Metan Propen Ankan Anken Parafin (n<n) Olefin

CH3-CH2-CH2-CH2-CH3 n- Pentan

CH3-CH3 + CH2=CH2 Etan Etilen CH4 + CH2=CH-CH2-CH3 Metan Buten-1 Cracking CH3-CH3 + CH2=CH-CH3 Etan Propen

CH2=CH2 + CH3-CH2-CH3 Etilen Propan CH2=CH2 + CH4 + CH2=CH2 Etilen Metan Etilen III.6.3. Ankin nno Cn Hn t Pd Paladi C H2 2 H2 2 () + Ankin Anken

Hiro

Anken

R-C C-R + H2 o t Pd R-CH=CH-R Th d: CH CH + H2 Pd t o CH2 CH2 Axetilen Hidro Etilen CH3 C CH + H2 Propin Hidro Pd t oGio khoa ha hu c 43 n: V Hng Thi

CH3 CH CH2 Propen Bin so

phn ng cng H2 vo ankin to ra ch yu l anken th dng H2 khng d v dng xc tc Palai (Pd) (khng dng Ni, Pt lm xc tc). III. 6.4. Dn xut monohalogen ca ankan tc dng KOH trong ru, un nng, to anken R-CH2-CH2-X 0

KOH / Ruou,t R-CH=CH2 + HX R-CH2-CH2-X + KOH 0 Ruou,t R-CH=CH2 + KX + H2O Th d: CH3-CH2-Cl + KOH 0 Ruou,t CH2=CH2 + KCl + H2O Clometan, Etyl clorua Etilen Kali clorua Nc CH3-CH2-CH2-Br + KOH 0 Ruou,t CH3-CH=CH2 + KBr + H2O III.6.5. ,- ihalogenankan tc dng vi bt kim loi km hay ng, thu c anken R-CH-CH-R + Zn R-CH=CH-R + ZnX2 X X Th d: CH2-CH2 + Zn CH2=CH2 + ZnBr2 Br Br Lu Ngi ta thng p dng phng php iu ch ny tch ly ring anken ra khi hn hp cc cht hu c. Cho hn hp cc cht hu c c cha anken tc dng vi nc brom th anken b gi li v c phn ng cng brom v to sn phm ha tan trong nc brom. Sau cho bt kim loi km vo, s ti to c anken. CnH2n + Br2 CnH2nBr2 CH3 CH Cl CH2 Cl + Zn CH3 CH CH2 + ZnCl2 1 ,2 Diclopropan Kem Propen Kem clrua CH3 CH Br CH Br CH3

+ Zn CH3 CH CH CH3 + 3,4 Dibrombutan 2 Buten ZnBr2 Kem bromua -Gio khoa ha hu c 44 n: V Hng Thi CnH2nBr2 + Zn CnH2n + ZnBr2 Sn phm cng brom Km Anken Km bromua Th d: Tch ly ring etilen ra khi hn hp gm hai kh metan v etilen. Cho hn hp hai kh trn qua nc brom c d. Tt c etilen b gi li v c phn ng cng brom. Metan khng tc dng vi brom dung dch, khng ha tan trong nc ca dung dch, thot ra khi bnh ng nc brom, thu c metan. Sau cho bt km lng d vo phn dung dch cn li, s ti to c etilen. Etilen to ra, khng ha tan trong nc, thot ra, thu c ring. CH4 + Br(dd) X CH2=CH2 + Br2 CH2-CH2 Br Br CH2-CH2 + Zn CH2=CH2 + ZnBr2 Br Br Br2(cn d) + Zn ZnBr2 Bi tp 24 9,7g hn hp A gm hai ru sau khi ehirat ha hon ton, thu c 4,564 lt hn hp kh gm hai olefin ng ng lin tip (171,99 0 C; 1,2 atm). a. Xc nh CTPT ca hai ru trn. b. Tnh %khi lng ca mi ru trong hn hp A. (C = 12 ; H = 1 ; O =16) S: 61,86% C3H7OH; 38,14% C4H9OH Bi tp 24 8,98g hn hp X gm hai ru. Cho lng hn hp X dng hi trn qua H2SO4(), un nng c s tch nc hon ton, thu c 3,7184 lt hn hp hi hai anken ng ng lin tip ( 180,18 0 C; 836mmHg).

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a. Xc nh CTPT hai ru trn. b. Tnh khi lng mi ru c trong hn hp X trn. (C = 12 ; H = 1 ; O = 16) S: 3,7g C4H9OH 5,28g C5H11OH Bi tp 25 Thc hin phn ng cracking propan thu c hn hp kh A gm: etilen, metan v propan cha b cracking. Hy tm cch ly ring etilen tinh khit ra khi hn hp A. Vit cc phn ng xy ra. Bi tp 25 Ly 2,24 lt (ktc) isobutan em thc hin phn ng cracking. Thu c hn hp A gm ba kh. Gio khoa ha hu c 45 n: V Hng Thi a. Tnh khi lng hn hp A. b. Trong hn hp A trn c 3,36g mt kh X m khi t chy to s mol H2O bng s mol CO2. Cn hai kh kia, mi kh khi t chy u to s mol H2O ln hn s mol CO2. Tnh hiu sut phn ng cracking v % th tch mi kh trong hn hp A. c. Nu phng php ha hc tch ly ring kh X ra khi hn hp A. (C = 12 ; H = 1) S: 5,8g hn hp A ; HS 80% ; 44,44% CH4 44,44% C3H6 11,12% C4H10 Bi tp 26 t chy hon ton 2,8g cht hu c A mch h cn dng 6,72 lit oxi (ktc). Sn phm chy ch gm kh cacbonic v hi nc vi s mol bng nhau. a. Xc nh cng thc chung dy ng ng ca A. b. Nu cho 2,8g cht A trn vo dung dch brom d th thu c 9,2g sn phm cng. Tm CTPT, cc CTCT c th c ca A. c tn cc cht ny. c. Cho bit A c mch cacbon thng, khng c ng phn cis, trans. Xc nh cng thc ng ca A. Vit phn ng A vi HCl v vit phn ng trng hp A. Tnh h s trng hp ca A nu polime thu c c khi lng phn t 210 000 vC (C= 12 ; H = 1 ; O = 16 ; Br = 80) S: C5H10 ; 6 CTCT ; n = 3000 Bi tp 26 t chy hon ton 3,36g cht hu c X mch h bng 8,064 lt O 2 (ktc) va . Sn phm chy ch gm CO2 v H2O c s mol bng nhau. a. Xc nh dy ng ng ca X. b. Nu cho 3,36g cht X trn tc dng vi nc brom d th thu c 12,96g sn phm cng. Xc nh CTPT v cc CTCT ph hp ca X. Gi tn cc cht tm c. c. ng phn X1 ca X c ng phn cis, trans. Vit phng trnh phn ng hirat ha X1 v phng trnh phn ng trng hp X1. Tnh khi lng phn t ca polime thu c nu h s trng hp l 4000. (C = 12 ; H = 1 ; Br = 80) S: X: C4H8 ; 224 000 vC Bi tp 27 14g hn hp hai anken A, B tc dng va vi 200ml dung dch KMnO4 1M. a. Xc nh CTPT ca A, B v tnh % s mol ca mi cht trong hn hp hai anken

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trn nu B l ng ng k tip sau ca A. b. Xc nh li cc CTPT c th c ca A, B nu A, B c t l s phn t gam tng ng l 1 : 2. (C = 12 ; H = 1) S: a. 66,67% C3H6 ; 33,33% C4H8 b. C6H12 , C2H4 ; C4H8 , C3H6 ; C2H4 , C4H8 Bi tp 27 Hn hp A gm hai olefin X, Y hn km nhau 28 vC trong phn t. Thy 5,18 gam lng hn hp A trn lm mt mu va 120ml dung dch KMnO4 0,5M. Gio khoa ha hu c Bin so 46 n: V Hng Thi a. Xc nh cc CTPT c th c ca X, Y. b. Cho bit ch c olefin c khi lng phn t ln (Y) mi c mt ng phn hnh hc duy nht (dng trans i vi n). Xc nh CTCT ng ca X, Y. Tnh % khi lng mi cht c trong hn hp A. (C = 12 ; H = 1) S: a. C4H8 , C6H12 ; C3H6 , C5H10 b. 32,43% C3H6 67,57% C5H10 Bi tp 28 Hn hp A gm hai hirocabon ng ng lin tip. t chy hon ton a gam hn hp A ri cho sn phm chy hp th ht vo dung dch X c ha tan Ba(OH)2 d, thu c 55,16g kt ta v dung dch Y. Khi lng dung dch Y nh hn khi lng dung dch X l 36,9g. a. Xc nh dy ng ng ca hai hirocacbon trn. b. Tnh tng s mol hai hirocacbon trong a gam hn hp A. c. Xc nh CTPT hai hirocacbon trong hn hp A. d. Xc nh CTCT ca hai hirocacbon trn. Bit rng mch cacbon ca chng c dng neo. Tnh khi lng mi cht c trong a gam hn hp A. (C = 12 ; H = 1 ; Ba = 137 ; O = 16) S: b. 0,05 mol d. 1,44g C5H12 , 2,58g C6H14 Bi tp 28 t chy hon ton x gam hn hp X gm hai hirocacbon mch h ng ng lin tip. Cho sn phm chy hp th ht vo nc vi trong d, thu c 50g kt ta v dung dch thu c c khi lng gim 19g so vi khi lng nc vi lc u. a. Xc nh dy ng ng ca hirocacbon trong hn hp X. b. Nu cho x gam hn hp X ha hi ht th thu c 3,024 lt hi ( 136,5 0 C; 76cmHg). Xc nh CTPT v tnh % khi lng mi cht trong hn hp X. (C = 12 ; H = 1 ; O = 16 ; Ca = 40) S: 40% C5H10 60% C6H12 CU HI N PHN III 1. Olefin l g? Hy cho bit cng thc chung dy ng ng ca n. 2. Vit CTCT ca cht 8-amino-2,7,7-trimetyl-4-etyl-3-n-propyl-5-isopropyl-2octen; c tn cht CH3-CH-CH2-CCH3-CHC2H5-CH2CH2-Cl CH3 CH=CH2 3. Lin kt l g? Lin kt l g? V hnh th d minh ha s xen ph obitan nguyn t to ra hai loi lin kt ny.

4. So snh di lin kt gia C vi C trong cc phn t etan, etilen v axetilen. 5. So snh di lin kt gia C vi O trong cc phn t ru etylic (CH3CH2OH) vi anehit axetic (CH3CHO); di lin kt gia N vi N trong cc phn t N2, H2N-NH2, CH3-N=N-OH. Gio khoa ha hu Bin so 47 n: V Hng Thi 6. So snh di lin kt gia C vi N trong cc phn t: Metylamin (CH3NH2), Ankyl isoxianat ( R-N=C=O ) v Nitrin acrilic (CH2=CH-CN). 7. Nu iu kin mt cht c ng phn cis, trans. Cho mt th d minh ha. 8. Vit CTCT cc ng phn cis, trans (nu c) ca: 1-Brom-2-clopropen; 1,2iphenyleten; Isobutilen; Heptaien-2,4 ( CH3-CH=CH-CH=CH-CH2-CH3 ). 9. Nguyn nhn no m c ng phn cis, trans? Ti sao buten-2 c ng phn cis, trans cn buten-1, cng nh n-butan khng c ng phn cis, trans? 10. Vit CTCT cc ng phn olefin ca penten m khi hp nc cho ta sn phm chnh l ru bc ba. Vit phng trnh phn ng khi cho etilen tc dng vi: Br2, dung dch KMnO4 v HCN. Vit phn ng ng trng hp gia propilen vi butaien-1,3. (B tuyn sinh i hc mn ha) 11. Cht do PVC c iu ch t kh thin nhin theo s sau (hs : hiu sut) CH4 hs 15% C2H2 hs 95% CH2=CH-Cl hs 90% PVC Hi cn bao nhiu m 3 kh thin nhin (ktc) iu ch c 1 tn PVC (bit CH4 chim 95% th tch kh thin nhin). (B tuyn sinh i hc mn ha) 12. Khi mt mt phn t H2O, axit HOOC-CHOH-CH2-COOH c th to thnh hai axit l ng phn cis, trans ca nhau. Vit CTCT hai axit ny. (B tuyn sinh i hc mn ha) 13. Khi cracking butan to ra hn hp gm parafin v olefin trong c hai cht A v B. T khi hi ca B so vi A l 1,5. Tm cng thc ca A, B. (B tuyn sinh i hc mn ha) 14. Hn hp kh A gm H2 v mt olefin CnH2n c t l s mol l 1 : 1. Cho hn hp A qua ng ng Ni nung nng, thu c hn hp kh B c t khi hi so vi H2 l 23,2. Hiu sut phn ng l b%. a. Tm biu thc lin h gia n vi b. b. Nu hiu sut phn ng b = 75% - Tm CTPT ca olefin. - t chy hon ton hn hp B v cho ton b sn phm qua bnh ng 128 gam dung dch H2SO4 98% th nng ca H2SO4 b pha long thnh 62,72%. Tnh % th tch ca mi cht trong hn hp B. Tnh khi lng mi cht trong hn hp B. (C = 12; H = 1; S = 32; O = 16) Gio khoa ha Bin so 48 n: V Hng Thi

hu

S: a. n = ) 100 46,4 (90,8 14 1b b. C4H8 60% C4H10 ; 20% C4H8 ; 20% H2 34,8g C4H10 ; 11,2g C4H8 ; 0,4g H2 15. A l mt hirocacbon. em t chy mt lng A cn dng 84 lt khng kh (ktc). Cho sn phm chy hp th ht vo 30 lt dung dch Ca(OH)2 0,01M, thu c kt ta T v dung dch D. Khi lng dung dch D ln hn so vi khi lng dung dch nc vi em dng l 21 gam. Nu em un nng dung dch D thy c xut hin kt ta. a. Xc nh CTPT ca A. Bit rng t khi hi ca A ln hn 2 v nh hn 2,8. b. Xc nh CTCT ca A, nu A c cu to dng trans. c. Vit CTCT v c tn tt c cc ng phn ca A. d. Tnh khi lng kt ta T. e. em hiro - ha A, thu c B. So snh nhit si gia B vi cc ng phn ca n. Khng kh gm 20% O2, 80% N2 theo th tch. Cc phn ng xy ra hon ton. (C = 12; H = 1; Ca = 40; O = 16) S: a. C5H10 c. 10 P d. 10 gam T 16. Cho hirocacbon A tc dng vi brom trong iu kin thch hp, thu c mt dn xut cha brom c t khi hi i vi hiro l 75,5. Xc nh CTPT, vit cc CTCT c th c ca A. Xc nh CTCT ng ca hirocacbon A nu A tc dng vi brom ch thu c mt sn phm hu c. ( thi khi A, 2004, c sa cha) (C = 12 ; H = 1 ; Br = 80) S: C5H12 17. Ti sao t gp anken trong t nhin, trong khi ankan gp rt nhiu trong t nhin? 18. Ti sao ngi ta gi anken l olefin? (Olefin ngha l g?) 19. Ti sao ngi ta c th cn c vo lng etilen sn xut ca mt nc hng nm nh gi nn cng nghip ha hc ca nc ?