Kiến thức về sơ đồ chuỗi phản ứng Hóa học hữu cơ: Phần 1

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Phần 1 tài liệu Sơ đồ chuỗi phản ứng Hóa học hữu cơ do PGS.TS. Nguyễn Xuân Trường biên soạn cung cấp cho người đọc kiến thức tóm tắt và bài tập chuỗi phản ứng hiđrocacbon, hiđrocacbon không no, hiđrocacbon thơm. Mời các bạn cùng tham khảo nội dung chi tiết.

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Nội dung Text: Kiến thức về sơ đồ chuỗi phản ứng Hóa học hữu cơ: Phần 1

547.076 GS.TS. NGUYEN X U A N T R U O N G S460D „ TT f—^ I'—^ i h 1^ CHuol P H A N urnl -JK rn r^i^*
sa DO ^4 I..' CHUOl PHAH UTHG WOA HOC Hiivco • * A Giup on tap he thong hoa kieh thtic • Giup di nhd va nhd nhanh kieh thiic • Danh cho hoc sinh Idp 10, 11, 12 • On thi tot nghiep THPT va luyen thi Dai Hoc Hl'i'r \ - • - ••• '1 100 ODI NHA XOAT BAN flAI HOC QUOC 6 I A HA NOI
T 6 M TAT KIEN THQC CO B A N vA BAI TAP C H U O I P H A N Q N G ^lyctc not daii. HIDROCACBON ChU(mgl. HIDROCACBON A. K I E N THirC C O BAN Hoa hoc la nganh khoa hoc nghifen cihi cac chat va su bien d6i cua cac cha't. Mu6'n chuyen chat nay thanh chat khac ta cho cac chat tac dung vdi nhau I. H I D R O C A C B O N NO, M A C H Hd (ANKAN) trong nhOng didu kien nha't djnh (xiic tac, nhiet d6, ap sua't, ...). 1. Cong thiic Chung: C„H2„,2 (n > 1) Kifi'n thiic hoa hoc chij yfe'u la kife'n thiic ve sir tuong tac giOa cac chSft xay ra 2. Ca'u tao trong phan ting hoa hoc va dugc diln ta bang phuong trinh hoa hoc. • Nguyfin tir C trong phan tir ankan d^u d trang thdi lai hoa sp' (cacbon tii: dian), goc hoa tri bang I09''28'. Chu6i phan ling giiip cac em 6n tap, he thC'ng hoa kien thiic mdt each sinh • Trong phan tir chi c6 lidn kd't a nen nguyen tir C quay dugc d l dang quanh d6ng va hieu qua nha't. true lien ket don C—C. Chudi phan ling giiip d l nhor, nhd lau boi kie'n thiic dirge torn tat ngan ggn 3. linh chat vat h dudi dang cac so do. Chu6i phan ling cung giiip ren luyen kha nang van dung kien • d didu kien thuomg : C, -> C 4 la chat khi thiic, chuSin bj t6't cho cac ki thi Tot nghidp Trung hgc ph6 thdng va Tuyen sinh Dai C, -> Ciftla chat long hoc - Cao dang. C|7 tro len la cha't ran Xin tran trgng gidi thieu cu6'n sach: • Khi so nguyen tijr C tang thi phSn tir khoi tang nen t" tang. Mach cacbon SO DO C H U O l PHAN IfNG HOA HOC H C X J C O cang phan nhanh thi be mat tid'p xiic cang giam nen lire hut giua cac phan tix Tac gia chan thanh cam on nhOng y kien dong gop cua ban dgc, nha't la ciia cac Thay Co giao va cac em hgc sinh. giam nen t" giam. • V i khong c6 lien ket hidro vdi nude ndn tat ca hidrocacbon no deu khdng tan Tac gid trong nude (ki nude) nhung tan nhieu trong dung moi huti co. 4. Tinh chat hoa hoc + Phan umg the halogen ^ C,|Hi|, ^. 3 + ZXT — — ^ C„H2„ + 2— Vi (III: CH4 + CI: ) CH3CI + HCI Metyl clorua (clometan) CH4 + 2C!2 > CH2C1, + 2HC1 Metylen clorua (diclometan) CH4 + 3 C I , > CHCI3 + 3HCI Clorofom (triclometan) CH4 + 4CI2 CCI4 + 4 H C ! Cacbon tetraclorua (tetraclo metan)
—. , Mx iv 1 Cac d6ng phSn cua metan cung tham gia phan iJng thfi' tucmg tir metan. Vf du: Mat khac : mx = my -> Mx > My - » dx/y = = ^ = > ' MY CI2, as CHj-CHa-CHj + CHj-CHj-CH.a + HQ 25° C Tir bi^u thiic: ^ =^ va dxA- = — ta se tinh duoc ny do do tinh duoc % ankan 2 — clopropan (57%) 1 — clopropan (43%) nx Pi "x CH3-CH2-CH3 2a^iL_^ CH3-CHBr-CH, + CHj-CH.-CH^Br + HBr bi nhiet phan 25°C + Phan umg oxi hoa 2-brompropan (97%) 1 - brompropan (3%) a) Oxi hoa hodn toan (san phim chinh) (san ph^m phu) Khi dd't cac ankan chay tao ra CO,, H-,0 va toa nhilu nhiet • Q o the' cho H a cacbon cac bac khac nhau. Brom hdu nhu chi the' cho H d cacbon bac cao. Flo phan ling manh lidt n6n phan huy ankan thanh C va HF. C„H2„,2 + Y ^- nC02 + (n + DH.O lot qua y6'u n6n kh6ng phan ting vori ankan. W ^ M ; C H 4 + 202 ^ C02 + 2H,0 ^ • Phan umg clo hoa va brom h6a xay ra theo co ch6' goc - day truyln. Nhdn xet: Khi d6't chay m6t hay m6t h6n hop cac hidrocacbon thu6c ciing day a) Bir6c khoi mao : d6ng dang ma thu duoc : cij-ci — ^ cr + cr "CO2 < " H 2 0 b) Buorc phat tri^n day truy^n : Hoac : no2 > l.Sncoj C H J I H + CI* - ) • 'CHi + HCl •CH3 + CI -f CI CH3C1 + cr -> Cac hidrocacbon do thu6c day dong ding ankan va CH31 H + CI* ^ ... "hh = " H J O - " C O 2 "hh =2(no2- ^ ' ^ " 0 0 2 ) c) Bixorc dut day truy^n h) Oxi hoa khdng hodn todn Cl' + Cr ^ CI. • Neu khong du oxi, ankan chay khdng hoan toan, khi do ngoai CO2 va HjO •CH3 + a * ^ CH3C1 con tao ra cac san ph^m nhu CO, mu6i than, khdng nhiimg lam giam nang •CH3 + *CH3 CH3-CH3 sua't toa nhiet ma con gay doc hai cho m6i truomg. + Phan ung tiich (gay lien ket C - C va C -H) • Khi C O chat xuc tac, nhiet do thich hop, ankan bi oxi hoa khdng hoan toan tao thanh dSn xua't chiia oxi. Vi du : "^f ) QH3^ + C „ _ , H , ( „ _ , ) , , (m>2; n-m>0) > CH3CH = CHCH3 + H2 CH4 + 0 , ^" „ > HCHO + H2O our-j 500°C CH3CH2CH2CH3 CH3CH = CH2 + CH4 200atni.300"C xt > CH2 = CH2 + CH3CH3 • Ne'u mach cacbon dai, khi oxi hoa c6 the' bi be gay : Nhdn xet: CHiCH,CH,CH3 + O, ' " ' I > 2CH3COOH + H , 0 Dudri tac dung cua nhidt va xuc tac Fe, Pt, ...), cac ankan kh6ng nhOng bi tach hidro tao thanh hidrocacbon khCng no ma con bj gay cac li6n + Phan umg phan huy k6't C - C d^ tao ra cac phan tir nho hem. • Phan hiiy boi nhiet: Gia sir ta c6 so d6 : 1 ()()()" c ankan crackinh Hon hdp X -> honh(?pY DSc biet: khi khac Trong phan umg crackinh s6 mol khi sau phan umg tSng nhimg kh6'i liromg kh6ng doi VI ham lirong C va H trong X va Y nhu nhau nx < n y -> P, < P,
• PhSn huy bai clo : + Mot so phmmg phap khac a) Tif nhom cachiia : C„H„,.3 + (n H- DCU ,„Hs.C^,c.rn, > + 2(n + DHQ AUCj+ I2H2O 4 A l ( O H ) 3 i + 3CH4 5. D i e u c h e (Di^u chd-AI4C, : 2AI2O3 + 9C ) Al^Q + 6C0T) a) Khai then- ti( ddu mo, klii thien nhien qua cue con dudng crackinh va chifng cat h) Ti(C vdH. : phc'in doan. Ni C + 2H. ^ CH4 h) Phuon^ phdp tdn^ mach cachon . .TOOT • Tdnghop Vuydc(Phap) II. H I D R O C A C B O N NO, M A C H V O N G ( X I C L O A N K A N ) 2C„H„„ ,X + 2Na ( C „ H 3 „ , + 2NaX J. Cong thitc chung: C„H2„ (n>3) Chu y: N6'u dung hai loai d3n xua't halogen c6 g6c ankyl khac nhau se thu 2. Tinh chat hoa hoc duoc h6n hop 3 ankan song kho tach khoi nhau vi chiing c6 nhi6t d6 s6i xa'p a) Phdn iOi}> cgng md vdni> ci'ia xiclopropan vd .xiclohutan X I bang nhau: R-R + 2NaX ^' > CH,-CH.-CH3 80° C R X + R ' X + 2Na R-R' + 2NaX propan R'-R' + 2NaX + Br2 CH2Br-CH2-CH2Br • T6ng hop Konbe (Dure) /,.? - dihrompropan 2 R C O O N a + 2 H . O -^2!^ R - R + 2CO,t + 2NaOH + H . t + HBr ^ C H , - C H 2 - C H 2 B r Anot Catot / - hiompropan c) Phuang phdp gidm much cachon Xiclobutan chi c6ng vdi hidro : Ni • Phuong phap Duma : > CH,-CH2-CH2-CH3 120°C R C O O N a + NaOH — R H + Na^COj Xicloankan vong 5, 6 canh tro len khdng c6 phan ting c6ng ma vong trong nhirng dieu ki^n trSn. Vidu: h) Phdn I'rng the CaO C H , C O O N a + NaOH — C H 4 + Na,COi t' t" Phan ling thd' a xicloankan tuong tu nhu a ankan. V i du : CaO a C H , ( C O O N a ) , + 2NaOH — S f i 2 _ ^ CH4 + 2 N a X 0 3 + Ch — + HC1 • Phuong phap crackinh : Q.^:.. + 2 — i r 2 £ ] H i 2 S — ^ C,„H2„, + C,„. „,,H2,„. ^, + 2 (m > 2, n > m) xiclopentan + Phuong phap gift nguyen mach cacbon • Hidro hoa anken, ankin, ankadien tuong iJng : + CU \ HCi QHi,, + HT ——> C„H2„ + 2 1° xiclohexan (•) Phdn I'fng oxi hoa hodn todn C,iH2„ - 2 + 2H2 ——> QiH,,, + 2 C„H2„+y02 nCO. + nH20 • D i tir ancol no, dcm chiic : C „ H 2 , „ , O H + 2HI — > C„H2„,2 + H2O + I2 C6H,2+ 9O2 ^ 6CO2 + 6H2O
3. »i6uche E l a : CH,CHO Ngoai viec tach trirc ti^'p tuf qua trinh chung cat ddu mo, xicloankan con diroc F la: Q H 4 didu che' tuf ankan. V i du : G la: C 4 H , H la: C a C CH3[CH.]4CH, ) 1 1 + Hj Cac phirong trinh hoa hoc : 4. iTng dung (1) A I 4 C , + 1 2 H , 0 ^ 4 A 1 ( 0 H ) , +3CH4 Ngoai viec dung lam nhien Vitu nhu ankan, xicloankan dugc dung lam dung m 6 i , lam nguydn lieu di^u chfi'cac chat khac. (2) CH,COONa + N a O H ^"^''^ > CH4 + Na.CO, xiclohexan t", xt o benzen + 3H. (3) (4) C H 4 + CI, 2CH4 > CH3CI '-'"""^ > Q H , + 2 H , + HCl 5. Cdch viet dong phdn mach vdng (5) 2CH.,C1 + 2Na CM, + 2NaCl • Ve vong 16n nha't roi thu nho dan, chii y t6 hop cac loai nhanh (neu c6). • Them cac nguyen t\X H vao mach de dam bao dung hoa tri I V ciia cacbon. (6) C,H, + C I , CH^Cl + HCl CH, CHj — CH, CH, (7) C , H 4 + H C 1 ->C,H,C1 H,C CH, CHj — C H , C H — CH3 (8) C , H 4 + Br, C,H4Br, xiclopropan xiclohutan metylxk 7 opropan (9) C,H4 + H,0 CjHsOH (10) 3 C , H 4 + 2 K M n 0 4 + 4 H 2 O 3C,H4(OH), + 2 K 0 H + 2MnO, B. B A I T A P C H u 6 l P H A N iTNG (11) CaC, + H , 0 C , H , + Ca{OH), Bai 1. (12) C,H, + 2 H , > C,H6 (6) » C3H5CI (13) C , H , + H , '''^^"-^ >C,H4 (17) (1)^ (14) C,H, + H , 0 Hg-'»4.so"c ^ C H 3 C H O (15) C,H, + H C 1 ->C,H,C1 CH5OH CH4(OH)3 (16) C , H 4 + H , ^'-'"^ ) C , H , (17) C , H , > C,H4 + H, •> Cao su Buna (18) 2 C , H , ^"4Ci.'oo"c ^ C4H4 (19) C4H4 + H , P-'co3.'"c ^ c , H , » C4^10 H (20) nC4H, > (C4He)„ (Cao su buna) Huong Akn giai (21) C4H4 + 2 H , > C4H,o Dap an A la: A I 4 C , (22) C4H,o ' " " " ^ C H 4 + C,He B la: CH.COONa D la: Q H j 8 9
Bai 2. Bai 3. 1. CH4 - U C , H . — . C H , C H O ^ C , H , O H ^ C 4 H , - ^ C 4 H | o Ancol iso-propylic C4H, + 2 H , 0 + H , t 45(rC OiO. t0 2. C H , C O O H + 2NaOH CH4 + Na.CO, + H , 0 5) C4H, + 2 H , C4H,„ 3. A I 4 C , + I 2 H 3 O ^ 3 CH4 + 4A1 ( O H ) , A I 4 C , + 12HC1 3 CH4 + 4AIC1, 6) C4H,o C , H , + CH4 A I 4 C , + 6H,S04 ^ 3 CH4 + 2AU(S04), 7) C H 3 - C H = C H , + H O H C H , - C H - CH3 Cnickinh, .0 l' 4. C,H« CH4 + C , H , OH .100^ c © 1) 2CH,COONa + 2 H , 0 , /^'^f' ^ ) C.H^+ 2C0, + NaOH + H,T 5. C + 2H3 - > CH4 lamlanhnhanh . o . vi k h u a n 6. CO, + 4 H , ^ CH4 + 2 H , 0 2) C,He + CK '"^"^"'^"^ ) C,H,,C1 7. CO + 3 H , ^ CH4 + H , 0 3) 2C2H5CI + 2Na ^ C,H,o + 2 N a a 0 4) C4H,o "''^'"^ > C , H , + CH4 8. CH,COONa + NaOH > CH4 + Na^CO, 5) CH4 + 0 , ) HCHO + H , 0 600" c 6()()"C 6) H C H O + 2 A g O > CO, + H^O + 4Ag>l. © 1) C3H7CI + NaOH,„j„g — ^ CiH^OH + NaCl
Cty TNHHMTVDVVHKhang Vift 2) C,H70H + CuO — ^ C H 3 - C H 2 - C H O + Cu + H3O XI,t ^ / 6) n C H , - C = C H CH3 1 ^ Mn" 3) C H , - C H , - C H O + - O , >CH3-CH,-COOH I I 2 " CH3 CH3 -C-CH- I 4) C H , - C H 2 - C H O + ^ O . > CH3-CH,-COOH C H 3 J„ (Bai 5, 6, 7, 8 ban doc tir viet P T H H ciia cac phan urng) 5) CH3 - C H - C H . + H C I - > C H 3 - C H - C H , ^ * ' Bai 5. Viet P T H H cua cac pu thirc hien chuoi bien hoa sau : CI a. A I 2 O 3 — • A I 4 C 3 — • m e t a n — > • m e t y l c i o r u a — • metilenclorua ^ 6) CH3-CH-CH,+NaOH,„a„g CH3-CH-CH3 + NaOH — • clorofoni — • tetraclometan OH b. axitaxetic natriaxetat — • m e t a n — ^ m e t y l c i o r u a ^ ^ e t a n — ^ etilen 7) C H 3 - C H - C H 3 + C u O ^ C H , - C - C H , + Cu + H . O c. butan — e t a n — e t y l c l o r u a — • b u t a n — • propen — ^ propan OH Bai 6. Bai 4. a) Cong thirc phan ti'r ciia hidrocacbon A la CiH,, (vong). Hay viet P T H H cua cac phan I'rng theo chuoi sau dudi dang cong thuc cau tao thu gon. Polipropilen +NaOH +CuO +0, > B - B > D ^ — E ^ xt. t" b) Dung cong thuc cau tao viet PTHH ciia cac phan irng theo so d6 sau : ankan A D cao su isopren ^ i-Br-, - C4H6Br2 ("i9t chat) 5 " CH, » E I > -C - C H - QH,o —< " D C4H6Br-, (hai chat) Hwong dan giai Bai 7. Hoan thanh cac chu6i phan irng sau : DCjH,, ) C,He+ C,H, Mir +D 2) n C H 3 - C H = C H . - XI.I" . f-CH-CH2- a. A B c -CH-CH2- I CH2-OCOCH3 CH. 3)nCH3-CH-CH2-CH3 > r C H 2 = C - C H = CH + 2H, b.CHd A — B F — • CH4 — • H2 CH, CH3 ^ E — * ^ F c. C 3 H 6 — • A | — • A2 — A 3 — • A4 NaOOCCH2COONa xl.t" , f-CH,-C = CH-CH,- 4)nCH2 = C - C H = CH2 d. C 3 H , - B2 — • Glixeron CH. CH3 C E • F de hidro ^ / 5) n C H 3 - C H - C H 2 - C H , CH3-C = CH-CH3^ e. C2H4Br2 CH, CH, B HjSO^d.t'' 12
-£{j^" (-1'""! pluin irnfi hoa hoc HiTii cir - I\'f>uypn \tiiiii Trir&ng g. C3H6 — • C, — • C2 — • C H 3 - C O - C H O C h u o n g 2. HIDROCACBON KHONG NO . , , • , _^ NaOHIg ^ AgNO^/NH, „ H2SO4 +CI2 A. K I E N T H t r c C O B A N h . 1.1 i c l o | * o p a n 2^A - 2 — B —-— D — • 1. A n k e n (olefin) • E F ,_^„„ G • H • pohme /. Cong thifc Chung : C,fl2,. (n >2) 2. Cdu tao _ B • E • G (CjHftO) • T r o n g phan tir c 6 m o t n d i d o i ( C = C ) v d i C l a i h o a sp- t a o g o c 120", phSng k. A t r o n g d o c 6 1 l i e n k^'t a b^n v a m o t l i e n k e t 7t k e r n b6n n e n a n k e n d d t h a m D • F H (C2H6O) g i a p h a n irng h o n a n k a n . Bai 8. V i e t P T H H ci'ia c h u o i p l i a n i r n g t he o s a d o sau : • N g u y e n tir C k h o n g q u a y diroc q u a n h l i a n ket d d i ( C = C ) l a m xuS't h i e n d d n g a. CaC2 • A • B: — • D • F • CH phan k h o n g g i a n ( d d n g phdn cis. trans). 3. Tinh chat vat li • T i r Q - > C 4 la chat k h f , Q C|« l o n g va t r d I6n t d n tai d a n g r a n . < • N h i e t d d n d n g chay va nhiet d o s d i t u o n g d d i tha'p, t i khd'i h o i n h d , t i n h t a n A —•C A ^ G J - * " Cao su Buna t r o n g nirdc k e m . • C a c a n k e n t h i r d n g phfln c u e (|.i ^ 0 ) va fi,„ > \i„,„„ d o d d cac d d n g phan trans - an ken n d n g c h a y a nhiet d p c a o h o n n h u n g l a i s d i d nhiet d d tha'p h o n so v d i cac d d n g phan cis t i r o n g I'rng. +HC1^ B i v ^BN a O H CH4-*- D E C2H5OH • A n k e n hau nhir k h d n g tan t r o n g nude va la nhOng chat k h d n g m a u . 4. Tinh chat hoa hoc c. CH4 — • A - • < ^ J^—• D — • E — • F — • HCHC L i e n ket n c i i a anken k e m ben At hi dut de tao thanh l i e n ket a v d i cac n g u y e n tir +2HCI^ B 7 +NaOH khac nen dh t h a m g i a phan I'rng c d n g , phan i h i g t r u n g h o p va phan ting o x i hda. + Phsin umg cong a) Cgni> //. —> ankan C„H2„ + H , — > C„H2,n.2 Nlian xet : K h i g i a i toan ciin l u u y : Goi X la h d n h o p a n k e n va ban d a u , Y la h d n h o p t h u d u p c sau p h a n iJng. T a cd : • N e u m o t h i d r o e a b o n m a c h h d phan u'ng vira d u v d i t h e o t i le m o l 1: 1 t h i d d la a n k e n . • N e u 2 h a y n h i e u a n k e n c d n g v d i H2 v d i c u n g h i e u suat t h i ta c d the' thay h d n h o p b a n g c d n g t h u c t u o i i g ducmg C - H C-H - + H . C - H - ^, r nank.n p i f = I n 2 Pif = "umk - n,,„ ' Chi'i y: K h d n g the' d u n g each nay neu cac anken c d n g h o p v d i H , k h d n g c u n g h i e u suat.
Sffcld chuSiphan li-ng hda hpc Httu ca- Nguyln XuQn Tru&ng 2CH,-Ci l - C H , + 2H,0 — f ^ CH3 - C H - CH3 + C H 3 - C H , - C H , O H • V i h6n hop X, Y c6 cung s6 mol C, H nSn d6't chay h6n hop A hay B d^u cho OH cung ke't qua : Ancol isopropylic Ancol propylic d6'tX = n^ d6'tY (spchinh) (spphu) ,^ 'o- va r» sinh ra do d6't X = n^Q va nu r, sinh ra do dot Y + Phan iimg trung hop 'CO2 'H,o t", xt -> [-c - C - ]„ Do do khi lam toan, neu gap h6n hop sau khi qua Ni/t° dem ddt (h6n hop Y ) thi thay vl ti'nh toan vdi h6n hop Y (thucmg phufc tap hem X ) ta c6 t h i dung cac Vidu: phan ling dot chay X de ti'nh nco ^ va UH ^ o- "CH, = CH, I-CH.-CH.-,. 12 polietilen (PE) • m^ = mv va nv < nX Mx < M Y ^ d (XA') = = A = ^ = - 1 < 1 (gia sCr t", Xt MY nCH, = (pH p [-CH, —CH-]„ X, Y do o cung dieu kien t°, ap sua't) CH, CH, h) Cdna halogen (CI.. Br,) polipropilen (PP) C„H,„ + X , (dd) cci.^ C„H,„X3 + Phan iimg oxi hoa ! I'' Nhan xet : a) Oxi hda hodn toan : • Phan ling lam mA't mau dung djch brom dirge dung d l nhan bi6't cac hop chait chiJa liSn ket doi, lien ket ba. C„H2„+ ^ "^^'"^ • Khd'i lugng ciia binh dung dung dich brom tang I6n la khoi luong ciia anken Nhan xet : Ih^p thu. • K h i d6't chay mot hidrocacbon hay nhidu hidrocacbon thu6c cung day d6ng • Neu bai toan cho m6t hay mot s6' hidrocacbon mach ho thuoc ciing day d6ng dang thu duoc : dang tac dung voi brom theo t i le mol 1: 1 thi cac hidrocacbon do la anken. "CO2 = " H 2 0 hoac n^o^ = 1-5 n^^^Q ^ Cac hidrocacbon do thu6c day d6ng c) Cons HA (A = halogen, O H " , OSO,H") dang anken hay xicloankan * • Quy tac Mac-c6p-nhi-c6p : K h i c6ng mot tac nhan bat d6'i H A (axit hoac • D6't chay h6n hop ankan + anken ( x i c l o a n k a n ) t h i n^^Q^ > n^^o nucfc) vao liSn ket d6i (C = C) ciia anken thi san p h i m chinh dugc tao thanh do phAn duong ciia tac nhan (H*) gin vao C ciia n6'i d6i mang di6n am lankan = "H2O ' nc02 (cacbon c6 bac tha'p hon) va phdn mang didn am ciia tac nhan (X~) gSn v^o cacbon ciia n6'i d6i mang dien duong (cacbon c6 bac cao hon). V i du : • D o t chay h6n hop anken + a n k i n (ankadien) t h i n^.^^ > n^^^Q va r*CH,-CH-CH3 (spchinh) CH, CH = CH2 + H" cr CI MI • t I • C H , - C H 2 - C H 2 C I (spphu) i) Oxi hda khon^ hodn toan V Dung dich KMn04 loang a nhiet d6 thucmg oxi hoa noi d6i ciia anken thanh 1,2- diol. • Giai thich quy tac : Do g6'c ankyl day electron lam cho lidn ket 71 bj phan cue, 3C„H3„ + 2KMn04 + 4 H , 0 3C„H2n(OH)2 + 2 M n 0 2 l + 2 K O H n6n ion duong dd gdn vao cacbon mang didn am va ngugc lai. Vi du : • Kha nang phan ling c6ng : H I > HBr > HCl > H F 3CH.=CH2 + 2KMn04 + 4 H , 0 ^ 3CH2-CH2 + MnO^J-+ 2 K O H • C6ng H , 0 - > ancol OH OH C H , = C H , + H3O '-^—^ CH.CH^OH t" (mau tim) 17 ' Ancbletylic
Nhdri xet: D i r a v a o sir b i e i i d o i m a u c u a d u n g d i c h ( d u n g d i c h m a u ti'm -> bi II, ANKADIEN (DIOLEFIN) nhat mau va c6 ke't tiia mau den xuS't hifen) phan ung nay duoc dung de nhan r a 1, C o n g thufc C h u n g : C„lii„-i (n S3) sir CO mat cua n6'i d6i, nO'i ba. + Dung djch K M n 0 4 dam dac, o t° cao oxi hoa manh lam dut mach cacbon tai 2, P h a n loai n6'i d6i cho xeton, axit cacboxylic hay C O , tuy theo CTCT cua anken. Phan c a n c l i vao vi trf ciia hai lien ke't d6i ma ngucri ta chia lam 3 loai : ling nay dugc dung de' xac dinh vj tri cua n6'i d6i dua vao ca'u tao cua san • Lien ke't d6i lien : Hai lien ke't d6i of l i ^ n nhau. V i du: ph^m oxi hoa. C H , = C = CH2 propadien (anlen) • Trong cong nghiep ngirofi ta oxi hoa nhe etilen de san xua't C H 3 C H O • Lien kd't doi lien hgp: Hai lien ke't d6i b each nhau m6t lien ke't don. V i du : 2CH2 = C H 3 + 0 , ^^cx,,c.cx, ^ 2CH3CHO CH2=CH-CH=CH2 CH2=C(CH3)-CH=CH2 t° + Phan ling the buta-1,3-dien (butadien) 2- metylbuta - 1,3 - dien (isopren) ' • Lien ke't doi khong lien hgp: Hai lien ke't d6i each nhau nhieu lien ke't don. • 6 nhiet d6 tha'p cac anken d l tham gia phan ling c6ng clo, nhimg b nhiet d6 cao (500 — 600°C) m6t s6' anken dSu day d6ng d i n g c6 t h ^ tham gia phan Vfdu: , 2 3 4 5 ling the' boi d o . V i du : CH2 = C H - CH2 - C H = CH2 penta - 1,4 - dien C H , = C H - C H 3 + C K — 5 5 2 1 ^ C H 3 = C H - C H 3 C 1 + HCl 3, Butadien v a isopren A l y l clorua a) Tinh chat vat li - Butadien hay divinyl la chat khong mau, c6 mui dac trung, t° = - 4''C • A l y l clorua dugc diing de d i l u che glixerol - Isopren hay 2- metylbuta-1,3- dien la cha't long, kh6ng mau, s6i b 34°C CH2=CH-CH2C! + a, + H,0 ^ CH,Cl-CH(OH)-CH2Cl + HCl Deu la nhQng chat khdng tan trong nu6c nhirng tan dugc trong cac dung moi CH2C1-CH(0H)-CH,C1 + 2NaOH ^ C H 2 0 H - C H ( O H ) - C H , O H + 2NaCl huu CO. 5. Dieu che h) Tinh chat hoa hoc + Dehidro ankan tUcfn^ i?ng + Phcin ifng cong C,.H,„,, ^ k i : ^ c „ H 3 „ + H, • Cong hidro p Ni + Dehidrat hoa ancol ti/cmg ifng CH,=CH-CH=CH, + 2H, -> C H 3 - C H 2 - C H 2 - C H 3 C„H3„„OH > C„H,„ + H , 0 Ni -> CH3-CH-CH2-CH3 t^no'c CH2 = C - C H = CH2 +2H2 + Cdn}> H2 vao ankin (xt: Pd) hoar ankadien (xt: Ni) tuang ifng CH, CH3 C„H,„_, + H3 — ^ C„H3„ t° • Cong halogen (X2) vd hidrohalogenua (HX) Butadien cung nhu isopren c6 t h ^ tham gia phan ling cong X2, H X va thucmg Vi du: C H H C H + ^ CH,=CH, t" tao ra h6n hgp cac san phslm c6ng- 1,2 va -1,4. 6 nhiet d6 tha'p uu tien tao ra C H 2 = C H - C H = C H , + H, — ^ CH3-CH,-CH=CH, ra san ph^m cong -1,2, nhiet d6 cao Uu tien tao ra san ph^m c6ng -1,4. + Phan i/ng trung hcq? + Crackinh ankan • Trung hgp — 1,4 d^ cho polime c6 tinh dan h6i cao (cao su) nCH,=CH-CH=CH2 —^'^"'"^ ) [—CH2-CH=CH-CH2—]„ + Loai HXra khoi dan xiidt monohalogen cua ankan tUcfng ifng polibutadien (cao su buna) C„H2„, ,X '^Q";""-"' > C„H2„ + H X p, t°, xt n C H 2 = C - C H = CH2 -CH2-C = CH-CH2|- + Loai X2 ra khoi dan xudt a, P - dihalogen cua ankan tuctng ifng CH, CH3 R - C H X - C H X - R + Zn — ^ R-CH=CH-R + ZnX, poliisopren (cao su isopren) 18 19
p, t ° . Xt n CH2 = C - C H = CH2 -CH2-C = CH-CH2 I CI tir c a c b o n (^^^^ = c = 3,29) d o d o cac a n k - 1 - i n c6 H l i n h d6ng, d ^ b i d u t d ^ clopren p o l i c l o p r e n ( c a o su c l o r e n ) d o n g v a i t r o tac nhftn t r o n g phan l i n g c6ng hoSc phan l i n g t h e ' v d i k i m l o a i . • M o t phSn CO the t r u n g hcrp - 1 , 2 d^' t a o t h a n h p o l i m e k h 6 n g d a n h 6 i . D i e u nay L i e n ke't ba ( C = C ) b a o g6m 1 l i e n ket a va 2 l i e n ket TT k e m b ^ n . T u y n h i e n iii>'' g i a i t h i c h t f n h d a n h o i k e m cm m 6 t s6' l o a i c a o su t 6 n g h a p . , lien ket 71 t r o n g l i e n ket ba hcri b^n h o n lien ke't 71 t r o n g l i e n ke't d o i nen phan nCH,=CH-CH=CH, p. t°, xt iJng c6ng v a o l i e n k e t ba x a y ra k h o hem phan l i n g c6ng v a o l i e n ke't d6i. -CH2-CH- 3. T i n h c h a t v a t l i ^ CH = CH. • ('1 nhiet d6 thircmg : n = 2 ^ 4 la chaft k h i ''^ ' 5. D i e u c h e a n k a d i e n n = 5 - > 16 l a chat l o n g + Dieu clie'hiita - 1J - dien n > 17 l a chat ran a) D e h i d r o h o a b u t a n hoSc buten a n h i ^ t d 6 c a o (GOO^C) c 6 m a t cha't x u c tac Cac a n k i n ra't ft tan t r o n g nude, tan duoc t r o n g m o t so d u n g m d i h i h i c o . I (Cr,03): 4. T i n h c h a t h o a h o c 1^^,, CH.CH^CH^CH, — ^ " • P - " ^ > C H 2 = C H - C H = C H , + 2H3 + Phan ihi}> coni> C4H8 '"'P'"^ ) CH:-CH-CH=CH, + H, a) Cgn^ hicfro: Phan l i n g x a y ra q u a 2 g i a i doan ( g i a i doan 1 t a o san p h ^ m d a n g cis) ' ' b) D e h i d r o h o a va h i d r a t hoa ancol e t y l i c n h d x u c tac ( Z n O hoac M g O v a AUO,) fH Ankin , 4_— >. Anken —> Ankan 2CH,CH,OH MgOiA\,o, ^ CH,=CH-CH=CH, + H ,+ 2H.O xt.t xt,t 400-50(1" C M u 6 ' n d i r n g phan l i n g 6 g i a i doan t h i i nha't ( a n k e n ) n g o a i t i Id m o l 1: 1 c ^ c ) D i tilf a x e t i l e n chu y d u n g cha't x i i c tac t h i c h h o p . * 2CH^CH _^ci/NH.ci '•i^i—> C H , = C H - C = C H — ^ - ^ - ^ CH,=CH-CH=CH, Pd, C H s C H + HV CH,=CH,! d ) T 6 n g hcrp K o n b e ( D u e ) : Ni, t° CH^CH + 2H. CHj-CHj^ 2 C H , = C H - C O O N a + 2 H . O — i ^ ! ^ C H , = C H - C H = C H , + 2C0,T Nhan xet : N e u g o i X l a h 6 n h o p a n k i n v a H , ban d d u , Y l a h 6 n h o p t h u duoc + 2 N a O H + H,T sau phan l i n g . T a c 6 + Dieu cheisopren • nH.pu =nx -nY^a,„^i„pu D e h i d r o h 6 a isopentan v a isopenten (san p h ^ m c r a c k i n h din m o ) ^ H a m l u g n g C, H t r o n g h a i h 6 n h o p X v a Y l a n h u nhau nen k h i g i a i toan d ^ CH3-CH-CH2-CH3 '"•"•"^ ) C H 2 = C - C H = CH2 + 2 H 2 d o n g i a n ta thay d6't chay h 6 n h o p Y bang dd't chay h 6 n h o p X . CH3 CH3 mx = mv v a ny < nx - > Mv < My d (X/Y)(= = r - = _ L = _ L < 1 (g,a MY "X CH3-C = CH-CH3 ^"•'^•"^ ) CH2=C-CH-CH2 + H, su X , Y d o 0 Cling d i e u k i e n ap sua't, nhiet d o ) ^ CgnsX2(X=CI, Br) III. ANKIN • Phan l i n g x a y ra q u a h a i g i a i doan (giai doan 1 c 6 n g trans). M u d ' n d t o g phan 1. C o n g thurc C h u n g : C „ H 2 „ . 2 (n>2) ting a g i a i doan t h i i nha't t h i cSn thuc h i e n a nhiet d 6 tha'p. 2. C a u t a o Q . H : , , —2 ' ^ QiH2„_2X2 ^ > C„H2n_2X4 • T r o n g p h a n tijf c 6 l i e n ke't b a ( C = C ) vdri n g u y a n tir C l a i h o a sp n e n phan t i r Nhan xet: CO ca'u t a o t h a n g , g o c h o a t r i 180°. • N o i c h u n g a n k i n l a m ma't m a u nu6c b r o m c h a m h o n a n k e n . 0 • K h d i lucmg c i i a b i n h d u n g d u n g d i c h b r o m tang l e n l a k h d i l u c n g ciia a n k i n • D 6 d a i l i d n ke't b a ra't ngdn ( 1 , 1 9 A ) nSn electron 6 gSn n h a n va b i nhan hut ha'p t h u . ,, m a n h n e n n g u y e n tir C a n6'i ba c 6 d o a m diSn I o n nha't t r o n g cac l o a i n g u y d n C6ngHX(X^a,Br.I) • Phan l i n g x a y ra q u a h a i g i a i doan v a g i a i doan sau k h o h o n g i a i doan t n r ^ .
Sff dd chuSi phan irng hda hpc Hihi cff - Nguyen Xuitn Trir&ng Cty TNHH MTVDVVHKhang Vift CH.CH + HCl ) CH3=CHCI — ^ -CH2 - C H - Cac phuang trinh hoa hoc : » CH = CH + 2AgNO, + 2NH3 -> AgC = C A g i + 2NH4NO3 Cl Bac axetilenua (mau vang nhat) Vinyl clorua Poli(vinyl clorua) R-C = CH + AgNO, + NH3 R - C = C A g i + NH4NO3 CH, = CHCl + HCl CH, - CHCl, ( 1 , 1 — dicloetan) (mau vang nhat) • Phan ung c6ng vao d6ng dang axetilen tuftn theo quy tac Mac-cop-nhi-cop. CH = CH + 2CuCl + 2NH3 -> CuC = CCui + 2NH4CI CHj-C^CH + HCl CH3 - C = CH2 > CH3-CCI2-CH3 D6ng (I) axetilenua (mau do) CI R - C = CH + CuCl + NHj -> R-C = CCui + NH4CI • CH,CHO • Trong day d6ng dang ankin chi c6 axetilen phan utig vdri cdc ion kim loai theo ti le mol 1: 2 con cac ank -1 - in khac phan ling theo ti IS mol 1 : 1 . (kh6ngb^n) • Co the dijng cac phan vrng trfin di nhan bife't axetilen va cac ank - 1- in. • Cac d6ng dang + HjO Xeton ,,»,^„., , - A . I . . . i • Axetilenua kim loai c6 th6' duac tach ra va phan ling vdi dung dich axit thu R,-C=C-R, + H O H ' R, - C H = C - R 2 R.-CH.-COR, duac axetilen (diing di tach cac chat ra khoi nhau) OH Vi du: AgC = CAg + 2 H a -> CH = CH T + 2 A g C l i (khdng bin) • H6n hap khi X (hidrocabon no, hidrocacbon khdng no, khi khac) di cham Nhan xet Neu mot hidrocacbon tac dung v6i nude tao ra andehit axetic thi qua blnh dung dung dich AgNO,/NH, thu duac hdn hap Y. Ta c6 hidrocacbon do la axetilen. " a n k - 1 - in = Hx " (nx > Hy) e) Cong axit axetic Iflbinh ling = ^ a n k - 1 - in xt,f T l k f t lua — Tlmufli ank - I - In C H ^ C H + CH,COOH ^ CH,COOCH = CH, -CH2 - C H - + Phan I'/ng oxi hoa COOCH3 a) Oxi hoa hoan toan (phan I'mg (hay) vinyl axetat poli(vinyl axetat) (PVA) C„H,„ _ , + O: nCO, + (n — 1 )H30 + Phan I'rng dime hoa vii trinie hoa Nhan xet : Khac vdi anken, ankin kh6ng triing hop thanh polime. Hai phan tij axetilen c6 • Neu bai toan cho dot chay mdt hay mdt sd hidrocacbon mach hd, thudc cung th^ c6ng hop vori nhau de' tao thanh vinyl axetilen. day ddng dang thu duac : 2CH = CH ""'f > CH. = CH - C = CH "cOj ^ " H J O '^^^^ " O j *^^'^"co2~^ hidrocacbon dd thudc day vinyl axetilen ddng dang ankin hay ankadien va Ba phan tir axetilen c6 the cong hap vdi nhau d6 tao thanh benzen. "hh = nH20-"co2 ^^^^ " h h = 2(l,5nco2-^o^) 3CH = CH ^ ^ ^ ^ C,H, • Dd't chay hdn hap ankan + ankin (ankadien) hoac anken + ankin (ankadien) + Phan I'fng the hang ion kim loai hoa tri I (Ag*, Cu*) + anken Nguyen tiJ H dinh vao cacbon mang n6'i ba linh d6ng hem ra't nhi^u so vdri H dinh v^o cacbon mang nd'i d6i va nd'i dan, do do no c6 the' bi thay thd' bang - Ne'u nco2 = "H2O ^ "-'kin = "ankan nguydn tir kim loai. Nhu vay, chi c6 axetilen va cac ank - 1 - in mdri tac dung - Neu nco^ "ankan H /
Sadd chuSiphdn li-ng htia hpc HOu ca - Nguyin Xudn Trir&ng D6't chay h6n hap anken + ankin (ankadien) thi Di tirddn xudt ch,'ra Ag cua ankin va ddn xudt chira halogen cua ankan • Phircmg phap tang mach cacbon. > n H , 0 va n. = nCO- - n AgC=C-R+R'Cl -> R'-C=C-R + A g C l i h) Oxi hoa khong hoan roan , Phan ling tuong tir doi v6i dSn x u ^ chufa Cu ciia ankin. Phan ung oxi hoa boi dung dich KMn04: Tuong tu anken, ankin dl bi oxi hoa bdi KMn04 sinh ra cac san ph^m nhu CO,, HOOC — COOH,... 3QH, + 8KMn04 ^ 3KOOC — COOK + SMnO^i + 2KOH + 2 H 2 O ^ B. BAI TAP C H u 6 l PHAN UNG C 2 H 2 + 2KMn04 + 3 H 2 S O 4 ^ 2C02t + 2MnS04 + K,S04 + 4 H 2 O Bai 1. SCHj-C^CH + 8KMn04 + 12H,S04 -)• (NaOOC)2CH=CH + SCO,! + 8MnO, + 4K,S04 + I 2 H 2 O 5CH3COOH Nhan xet : Co th^ diing phan ung lam mat mau dung dich thu6'c tim di nhan C2H5OH C2H4Br2, biet cac ankin. So vdi anken thi t6c d6 phan utig didn ra cham hon. n 5. Dieu che + Dieu che axetilen C2H,C1 a) Ti( metan : Phuomg phap chi'nh d^ di6u ch6' axetilen trong c6ng nghi6p hifin nay la nhiSt phan metan a 1500°C, phan iJng thu nhiet manh. 1500°C 2CH4 H,0 QH|o h) Tic than da, da v6i -> CaC, (dat den) CH Hiro'ng dan giai { 500° C Than da -> than c6'c (C) 1. NaOOC-CH=CH-COONa + 2 N a O H — ^ C2H4 + 2Na2C03 ; CaCOj - ) C a O + CO,T 2. C2H4 + B r 2 - > C2H4Br2 CaO + 3C 2000° c CaC + CO 16 di^n 3. C2H4Br2 + Zn ^ C2H4 + ZnBr2 CaC, + 2H,0 ^ Ca(OH), + C H ^ t '"''^ 4. C3H4 + [O] + H 2 O '""^""'^ > C2H4(OH)2 Nhan xet : 6 nhOng nod c6ng nghidp din khi chua phat trien nguofi ta thuong Hoac vidt: C2H4 + 2KMn04 + 2H2O C2H4(OH)2 + 2Mn02 + 2KOH di^u che Q H , theo phuong phap trdn. 5. nCH2=CH2-> [-CH2-CH2-],, ; c) TCr C va H2: 2C + H , "^""^"""^ ) CH, 6. C 4 H , o '^^"''"'^ ) C 2 H , + C 2 H 4 di$n ' ' Ni.l" d) Tii muoi axetilenua 7. C H . + H , ' -> C 2 H , AgC = CAg + 2HC1 -> C H = C H T + 2AgCl^ 8. CjHe - ->C2H4 + H2; CuC = CCu + 2HCl ^ C H s C H T + 2CuCli 9. C H 4 + H2O . , C2H3OH + Dieu chedong dang cua axetilen loang, I a) Dehidio hoa ankan ti/crng I'/ng ' Q,H2„ + 2 ^ > C,iH2„ _ 2 + 2 H 2 10. C H , O H - ^ i ^ ^ C 2 H 4 + H2O - mrc h) Di ti( dan xudt di halogen 11. C2H5CI + NaOH — ^ C2H.,0H + N a Q H X I I 12. Q H , O H + HCl C2H5CI + H2O an col R, - C - C - R , + 2KOH -> R , - C s C - R 2 + 2KX + 2H,0 I I 1 3 . C H , + Cl2 ->C2H,C1 +HC1 X H
Sffdb chudipItdn li-ng luiu lt(>c HCru cff ~ Nguyin Xu&n Trir&ng cry TNHHMTVDVVHKhang Vi?l Bai2. 2. CH3 - C H - C H , + NaOH C H , - C H - C H , + NaBr 1. Ancol butylic ^ Butilen ^ Butan ^ MetanAxetilen Br OH 3. nCH,-CH=CH, -> f - C H - C H 2 ^ 8 7 6 Etilen « - Brometilen C3H4 + ZnBr, 3. CH,=CH-CH=CH, + Br, Br Br © 1. 2CH,COONa + 2H,0 _ J ! E ^ C 2 H , + 2CO. + 2NaOH + H^.T ^CH2-CH=CH-CH2 2. CH6 — ^ C H 4 - i - H, Br Br 3. C3H4 + 2KMn04 + 2H,0 ^ C3H4(OH)2 + 2MnO, + 2KOH 4. CH,=CH-CH=CH, + Br, ->• C H , - C H - C H - C H2 4. a H 4 + HCI ^ C,H,C1 " " 1 ^ 1 I I Br Br Br Br 5. CH,C1 + 2 Na + C\-C.H, -> C4H,o + 2NaCl 5. nCH2=CH-CH=CH: [-CH2-CH=CH-CH2-]„ 6. C4H,o ^"^'^'"'^ > CH4 + C,H, 6. CH2=CH-C=CH + H2 CH2=CH-CH=CH2 7. C,H, + [O] + H.O "^^""-^ ) C,H,(OH)3 © 1. CH.,-CH=CH2 + HBr -> CH3 - C H - CH3 7. 2CH=CH ) CH,=CH-OCH Br
Sar ad chuSi ph6n lirng hda hpc HOu ctr - Nguyin XuSn Tru&ng 2) C H , = C - C H ^ C H 2 'l' > f-CH2-C = CH-CH2-' Bai 4. CH, CH3 2 3 4 ^ Cao su buna 1. Glucoza *• Rirooi etylic — ^ B u t a d i e n - 1,3
8 ) C,H, + 4 [ 0 ] '""^'^""^ > HOOC —COOH f-CH-CH, + nNaOH-> nCHjCOGNa + CH-CH2- I Hoac vilt: 3C,H, + 8KMnO, + 4HjO 3(COOH), + 8Mn02 + 8 K O H OCOCH3 OH 9) CH,-CHCl3 ^ CH = CH + 2HC1 10) CH = CH + 2HC1-> CH, - CHCl, e 1) CaCO, 900" r ^ CaO + CO. 2000"f 11) AgC ^ CAg + 2HCI -> CH = CH + 2AgCli 2) CaO + 3 C ^ CaC, + CO 12)CH = CH + A g , 0 -> AgC = CAg + H , 0 3) CaQ + 2H2O - > C2H2 + Ca(OH)2 Hoac Viet: CH = CH + 2f AgCNHO^J^OH" AgC = CAg + 4NH3 + 2H2O Hay CO the vid't CaC, + 2H" -> C2H2 + Ca-* 13) 2C2H, 4) C2H2 ) CH2=CH-C=CH 14) 2CH4 lilm lanh nhanh > LI C.H2 i + l O 3H2 Pd > CH,=CH-CH=CH, 5) CH2=CH-C=CH + H2 Bai 6. Ni -> CH3-CH,-CH=CH, 6) CH2=CH-CH=CH2 + H2 1. Tetrabrom axetilen — A x e t i l e n — ^ Andehit axetic — A x i t axetic 7) CH3-CH2-CH=CH2 + H . ^' > C4H10 — V i n y l axetat — ^ Polivinyl axetat — ^ Polivinylancol 8) C4H,o > CH4 + C 3 H , 2. Da v6i — ^ Voi s6'ng CaC. C.H. Vinyl axetilen e 1) C2H4Br2 + 2KOHd ) C2H2 + 2KBr + 2H2O — ^ Divinyl — ^ Buten — ^ Butan — P r o p e n . 2) C2H2 + 4 [ 0 ] '''"^^""^ ) HOOC-COOH 3. Dibrom etilen —!—> Axetilen — ^ Axit oxalic — ^ Oxalat natri 3) HOOC-COOH + 2NaOH ^ (COONa). + 2H2O — ^ Hidro — ^ Etilen — ^ Etilen glycol — ^ Axit oxalic. 4) NaOOC-COONa + 2NaOH -> H . + 2Na2C03 I Pd 4. C.H.. ^ CH,COOCH=CH2 — -> P.V.A 5) H2 + C2H2 > CH2=CH2 dd KMnO. 6) CH2=CH2 + [O] + H . ^ HO-CH.-CH,-OH Cupren CH,CHO 7 ) HO-CH2-CH2-OH + 4[0] '''"'^""^ > HOOC-COOH + 2H2O OH I O 1) C2H2 + C H 3 C O O H — ^ CH3-COOCH=H2 5. C H . - C ^ C H - ^ C H 3 - C - C H 2 CH3-C-CH3 CH3-C-CH3 2) nCH3-COOCH=CH2 -CH-CH2- OH OH O ^0CbCH3 6. RBr, -> C,H. A — UB E ^ -CH-CHo 3) C H 3 C O O H = CH, + NaOH CHjCOONa + C H 3 C H O 4) C2H2 + H2O ^2lo"r >CH3CHO Hirong dan giai Ca 5) n C H ^ C H 280"(• [-CH=CH-1 O I) C2H4Br4 + 2Zn C,H, t + 2ZnBr2 Hay (CH)2„ 2) CH^CH + H , 0 ) CH3CHO • © 1) CH3-C=CH + H 2 O ^ CH3 - C - C H 2 OU—OU ( 3) CH,CHO+ ^ O . - ^ ^ ^ C H . C O O H OH OH 4) C H 3 C O O H + CH=CH -> CH3COOCH=CH2 I 2) C H 3 - C - C H 2 +H2O 5) nCH3COOCH=CH, -CH-CH2 - CH3-C-CH3 OH OCOCH 3 OH 30
OH I Hudng dan giai 3)CH3-C-CH3 -> C H 3 - C - C H 3 + H.O (1) 2CH, ,- '.^'"u"': . >CH = CH + 3 H , lam lanh nhanh ^ OH O .0 (2) 2 C H = C H — ^ ^ ^ ^ C H = C - C H = CH2 1) CH.Br. + 2KOH > Q H ^ t + 2KBr + 2H,0 2) 3 Q H , > QH, (3) CH = C - C H = C H 2 + H 2 Pd/PdC03 >CH,^CH-CH=:CH. 3) QHft + QH4 ^ Q H , - C H , - C H 3 4) Q H , - C H . - C H , > QH,-CH=CH, + H , (4) CH2 = C H - C H ^ C H 2 + 2 H 2 >CH3-CH2-CH;-CH3 5) Q H , - C H = CH, - -CH-CHj-^ (5) CH3-CH2-CH2-CH3-^5^^CH4+CH3-CH=CH2 Bai 9. Vid't phuomg trinh hoa hoc cua cac phan urng trong chu6i bife'n h6a sau (bifi't 6) Q H , + H: CH,=CH: A, B, C, D, E, F la cac hidrocacbon): Bal 7. Hoan thanh so do phan urng sau : Hu-tfng dan giai A: C H : ; B: Q H , ; C: C,H^- D: C H , ; E: C H 4 606 I5i«)"c (I) 2CH, ,, , , , , >CH s C H + 3 H , lam lanh nhanh ^ (1) (3) CH, -C2H2 C4H 4"4 (2> 2CH = CH- 11.1 ->CHsC-CH-CH, C2H6 C2H4 (3) C H = C - C H = C H . + 3 H - ^CH3 - C H - C H 2 - C H 3 Hirong dan giai (4) C H 3 - C H 2 - C H 2 - C H 3 >CH3-CH3+CH2^CH;, ^lA I5()()"c (1) 2CH, -»-CH = CH + 3 H , lam lanh nhanh (5) C H 3 - C H 3 ) C H ^ C H + 2H2 (2) 3CH^CH ^ )CH 6"6 (6) C H ^ C H + H , '"^"''"^ >CH2^CH2 (3) 2 C H ^ C H ) C H ^ C - C H = CH, XI.I (7) CH3-CH3 -j-CHj =CH2 +H2 Pd/PdCO (4) CH = CH + H , ^CH2 =CH2 (8) CH2=CH2+H2 ^CH3-CH3 (5) C H s C H + 2 H 2 - ^ J p ^ C H 3 - C H 3 Bal 10. Viet phiromg trinh hoa hoc ctia cac phan li^ng trong chu6i bie'n hoa sau (bie't Bai 8. Hoan thanh so do phan irng sau : A, B, C, D, E la cac hidrocacbon): (1) C3H8 (8) CH4 C4H4 Hirong dan giai A: CH4; B: C,H,: C ' .H,o; D: QH^; E: C H 4 32 33
(1) C H , - C H ^ - C H ^ - C H ^ "" >CH^+CH3-CH =CH^ (7) CH2=CH2+H2 >CH3-CH3 (2) CH^-CH=CH2+H2-^^^^CH3-CH2-CH3 (8) CH3-CH3 > C H ^ C H + 2H2 (3) CH.-CH.-CH, >CH^+CH^=CH^ (9) CH= CH + | 0 2 - ^ ^ 2 C 0 2 + H 2 0 (4) CH3-CH2-CH2 -CH3 ) C H 3 - C H 3 + C H 2 =CH2 (10) C4H4+5O2—^4C02+2H20 • (5) CH3-CH3 " " " > C H ^ C H + 2H3 (11) c,H,+y02-^4C02+3H20 (6) CH^CH + H, ^'^"''^'^"^ )CH2^CH2 (12) C4H,„+y02-^4C02+5H20 (7) CH3-CH3^^^^CH2-CH2 + H2 (13) C2H4+4O2—^2C02+2H20 (5) CH3=CH2+H2 >CH3-CH3 (14) C2H^+-^02^%2C02+3H20 Bai 11. Viet phirong trinh hoa hoc cua cac phan irng trong chu6i bien hoa sau (bifi't A , B, C, D, E, F, G la cac hidrocacbon) : Bai 12. Hoan thanh chu6i bid'n doi sau : (4) PE (5) Propan - > X ^-^ etyl hidrosunfat (2) |(4) AUCs-^ A - ^ B C 0 2 ^ E etylen oxit Huo'ng dan giai G-^ F X la CH,=CH3 (7) (1) C H , = C H , ) (-CH3-CH.-)„ Hirong dan giai A : CH4; B: C,H,; C: QH4; D: C4H,; E. QH,o; F: C H 4 ; G: C H ^ (2) QHg ) CH4 + CH,=CH3 (1) Al^C3 + i 2 H 2 0 >3CH^+4A1(0H)3 (3) CH,=CH2 + H O S O , H > CHj-CH.OSO.H (4) C H , = C H , + ) CH2-CH2 (2) 2CH, 'f'"'"^; , > C H ^ C H + 3H2 - - - Bai 13. Hoan thanh chu6i bid'n d6i sau : ^ l a m lanli nhanli 2 Metan A — ^ B — ^ C — ^ polime (3) 2 C H = C H - ^ ^ ^ C H ^ C - C H = CH2 Huo'ng dan giai (4) C H ^ C - C H ^ C H , ' ' ^ ' ^ ' ' ^ ' ^ " 3 >CH2 = C H - C H = C H 2 AlaaH,,BlaCH,=CH-C=CH,Dla CH2=CH-CH=CHohoSc J CH,=CH-CH(C1)=CH2. Polime la poll (butadien) hoSc poll (cloropren) (5) CH2 - C H - C H = C H , + 2H2 )CH3 - C H j - CH2 - CH3 Bai 14. Hoan thanh chu6i bien d6i sau : (6) CH3 - C H , - C H 2 - C H 3 >CH3 - C H 3 + C H 2 = C H 2 ( X ) (hidrocacbon) ( Y ) - > etyl clorua. X , Y c6 the' la Cha't n^o ? Hoan thanh so do phan iJng tren. 34 35
Cty TnrHHUTTVTfvmiinang rip Hirdnng dan giai 5 2CH, c»cig.NH4Ci ^ c H , = C H - O C H (X) (hidrcKacbon) -> (Y) -> etyl clorua ' • l(X)"C X c6 the' la C2H2 hoac C4H,o 6. C H , = C H - C ^ H -K H, ' " ' ^ ' ' ^ > CH,=CH-CH=CH, - Ne'u X la Q H , thl Y la C,H4 hoSc QH^ - Ne'u X la C4H,o thl Y \h C.H^ 7. nCH2=CH-CH=CH2 — ^ ^ H ^ - C H = CH-CH2>„ V J?0 V i du: X la C4H10 thl Y la QHj Crackinf! C4H 10 ^ CH,=CH, + C H , - C H , -» C H 3 — C H , — C H , - < : H , 8. CH,=CH—CH=CH, + 2H2 "* t"c CH3-CH3 + a, ) CH3CH2C1 + H Q Bai 17. Hoan thanh chu6i phan umg sau : B^i 15. Hoan thanh chudi bie'n d6i sau: C,H •2"6 (A,B. D chi chura 2 nguyen t6 C va H ) C4H4 (A) (5)' (6) (3) (2) C H 4 ^ A2H2 ^ C2H4 JII^ PE Axetilen (1) etan ,,(8) \B)_(5)^ (D)' C2H4(OH)2 Hirong dan giai Hv&ng dan giai (1) HC=CH + 2H, ) QH^ , c.H, > CH4 +C,H4 (2) H C ^ C H + > CH,=CH, (3) CH,=CH.+ H. 2, 2CH4 Q H , + 3H, (4) 2C,H, ) CH3=CH-C^H 13 2C,H, "^"^'Z'^"^"^' > CH,=CH-C=CH 1()()"C (5) CH,=CH-C=CH + 3 H , "'""^ > CHj-CH^-CH^-CHj Pil/HfiCO, „ „ 4. CM, lU ^ QH4 (6) C H j - C H . - C H . - C H , ''"''""^ > Q H , + CH2=CH, t"c Bai 16. Hoan thanh chu6i phan umg sau : 5. C,H4 + H , Q-2"6 H (1) (2) (3) A L4^3 C CH. CH3CI CH2CI2 6. QHfi "'-'"^ > C,H4 + H3 (4) (5) (7) Cao Su BuNa 7. nC,H4 - " - i ^ B ^ K'H2-CH,-f„ C 2 H 2 — ^ C4H4 ^ C4H, 8. 3QH4 + 2KMn04 + 4 H : 0 -> 3C,H4(OH), + 2MnO, + 2KOH (8) C4H10 li 18. Hoan thianh chu6i phan I'mg sau : CsHgCI Hirang dan giai 1. AI4C3 + 3H.O -> 4Al(OH)3 +3CH4 HgCOONa JIL CH. C• 2H" 2, J I U 11 Toluen TNI 2. CH4 + CU -» CH,C1 + H Q 3. CH3C1 + a. CHjQ, + HCl C2H6 p - CloToluen 15(X)"C,lln 4. 2CH4 > Q H , + 3H2