sơ đồ chuỗi phản ứng hóa học hữu cơ

Mu6'n chuyen chat nay thanh chat khac ta cho cac chat tac dung vdi nhau trong nhOng didu kien nha't djnh xiic tac, nhiet d6, ap sua't, ..... Chu6i phan ling giiip cac em 6n tap, he thC'

A Giup on tap he thong hoa kien thiic

• Giup de nhd va nhd nhanh kien thUc

• Danh cho hoc s " "

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

ODI

100

^lyctc not daii

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

trong nhOng didu kien nha't djnh (xiic tac, nhiet d6, ap sua't, )

Kifi'n thiic hoa hoc chij yfe'u la kife'n thiic ve sir tuong tac giOa cac chSft xay ra

trong phan ting hoa hoc va dugc diln ta bang phuong trinh hoa hoc

Chu6i phan ling giiip cac em 6n tap, he thC'ng hoa kien thiic mdt each sinh

d6ng va hieu qua nha't

Chudi phan ling giiip d l nhor, nhd lau boi kie'n thiic dirge torn tat ngan ggn

dudi dang cac so do Chu6i phan ling cung giiip ren luyen kha nang van dung kien

thiic, chuSin bj t6't cho cac ki thi Tot nghidp Trung hgc ph6 thdng va Tuyen sinh Dai

hoc - Cao dang

Xin tran trgng gidi thieu cu6'n sach:

SO DO C H U O l PHAN IfNG HOA H O C H C X J C O

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

• Nguyfin tir C trong phan tir ankan d^u d trang thdi lai hoa sp' (cacbon tii:

dian), goc hoa tri bang I09''28'

• Trong phan tir chi c6 lidn kd't a nen nguyen tir C quay dugc d l dang quanh true lien ket don C—C

3 linh chat vat h

• d didu kien thuomg : C, -> C 4 la chat khi

C, -> Ciftla chat long

C|7 tro len la cha't ran

• Khi so nguyen tijr C tang thi phSn tir khoi tang nen t" tang Mach cacbon cang phan nhanh thi be mat tid'p xiic cang giam nen lire hut giua cac phan tix giam nen t" giam

• V i khong c6 lien ket hidro vdi nude ndn tat ca hidrocacbon no deu khdng tan trong nude (ki nude) nhung tan nhieu trong dung moi huti co

4 Tinh chat hoa hoc + Phan umg the halogen ^

Vi (III:

CH4 + CI: ) CH3CI + HCI

Metyl clorua (clometan)

Cac d6ng phSn cua metan cung tham gia phan iJng thfi' tucmg tir metan Vf du:

(san phim chinh) (san ph^m phu)

• 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

lot qua y6'u n6n kh6ng phan ting vori ankan

• Phan umg clo hoa va brom h6a xay ra theo co ch6' goc - day truyln

a) Bir6c khoi mao :

CH2 = CH2 + CH3CH3

Nhdn xet:

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

k6't C - C d^ tao ra cac phan tir nho hem

Gia sir ta c6 so d6 :

ankan khi khac Hon hdp X crackinh -> honh(?pY

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,

+ Phan umg oxi hoa

a) Oxi hoa hodn toan

Khi dd't cac ankan chay tao ra CO,, H-,0 va toa nhilu nhiet C„H2„,2 + Y ^- nC02 + (n + DH.O

W ^ M ; C H 4 + 202 ^ C02 + 2H,0 ^

Nhdn xet: Khi d6't chay m6t hay m6t h6n hop cac hidrocacbon thu6c ciing day d6ng dang ma thu duoc :

" C O 2 < " H 2 0

Hoac : no2 > l.Sncoj

-> Cac hidrocacbon do thu6c day dong ding ankan va

"hh = " H J O - " C O 2 "hh = 2( n o 2 - ^ ' ^ " 0 0 2 )

h) Oxi hoa khdng hodn todn

• Neu khong du oxi, ankan chay khdng hoan toan, khi do ngoai CO2 va HjO con tao ra cac san ph^m nhu CO, mu6i than, khdng nhiimg lam giam nang sua't toa nhiet ma con gay doc hai cho m6i truomg

• Khi CO chat xuc tac, nhiet do thich hop, ankan bi oxi hoa khdng hoan toan tao thanh dSn xua't chiia oxi V i du :

CH4 + 0 , ^" „ > HCHO + H2O o u r - j

200atni.300"C

• Ne'u mach cacbon dai, khi oxi hoa c6 the' bi be gay : CHiCH,CH,CH3 + O, ' " ' I > 2CH3COOH + H , 0

+ Phan umg phan huy

• Phan hiiy boi nhiet:

1 ()()()" c DSc biet:

• PhSn huy bai clo :

Chu y: N6'u dung hai loai d3n xua't halogen c6 g6c ankyl khac nhau se thu

duoc h6n hop 3 ankan song kho tach khoi nhau vi chiing c6 nhi6t d6 s6i xa'p

XI bang nhau:

R - R + 2NaX

R - R ' + 2NaX

R ' - R ' + 2NaX

• T6ng hop Konbe (Dure)

2RCOONa + 2H.O -^2!^ R - R + 2 C O , t + 2NaOH + H t

Anot Catot

c) Phuang phdp gidm much cachon

• Phuong phap Duma :

RCOONa + NaOH — R H + Na^COj

R X + R'X + 2Na

Vidu:

CaO t' CaO

CH,COONa + NaOH — C H 4 + Na,COi

t"

CH,(COONa), + 2NaOH — S f i 2 _ ^ CH4 + 2NaX03

• Phuong phap crackinh :

Q.^: + 2 —ir2£]Hi2S—^ C,„H2„, + C,„ „,,H2,„ ^, + 2 (m > 2, n > m)

+ Phuong phap gift nguyen mach cacbon

• Hidro hoa anken, ankin, ankadien tuong iJng :

QHi,, + HT ——> C„H2„ + 2

1°

• Di tir ancol no, dcm chiic :

+ Mot so phmmg phap khac

a) Tif nhom cachiia :

J Cong thitc chung: C„H2„ (n>3)

a) Phdn iOi}> cgng md vdni> ci'ia xiclopropan vd xiclohutan

3 » i 6 u c h e

Ngoai viec tach trirc ti^'p tuf qua trinh chung cat ddu mo, xicloankan con diroc

didu che' tuf ankan V i du :

4 iTng dung

Ngoai viec dung lam nhien Vitu nhu ankan, xicloankan dugc dung lam dung

m6i, lam nguydn lieu di^u chfi'cac chat khac

t", xt

o

benzen

+ 3 H xiclohexan

5 Cdch viet dong phdn mach vdng

• 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

(1) A I 4 C , + 1 2 H , 0 ^ 4 A 1 ( 0 H ) , + 3 C H 4 (2) CH,COONa + NaOH ^"^''^ > CH4 + Na.CO, (3) C H 4 + C I , > C H 3 C I + HCl

(4) 2CH4 '-'"""^ > Q H , + 2 H ,

(5) 2CH.,C1 + 2Na CM, + 2NaCl

(6) C,H, + CI, CH^Cl + HCl

(7) C , H 4 + H C 1 ->C,H,C1 (8) C , H 4 + Br, C,H4Br, (9) C , H 4 + H , 0 CjHsOH

(11) CaC, + H , 0 C,H, + Ca{OH),

(13) C , H , + H , '''^^"-^ > C , H 4 (14) C,H, + H , 0 Hg-'»4.so"c ^ C H 3 C H O

9

6) H C H O + 2 A g O > CO, + H^O + 4Ag>l

1) C3H7CI + NaOH,„j„g — ^ CiH^OH + NaCl

2) C,H70H + CuO — ^ CH3-CH2-CHO + Cu + H3O

b axitaxetic natriaxetat — • metan—^ m e t y l c i o r u a ^ ^ etan—^ etilen

c butan — e t a n — e t y l c l o r u a — • b u t a n — • propen — ^ propan Bai 6

a) Cong thirc phan ti'r ciia hidrocacbon A la CiH,, (vong) Hay viet PTHH cua cac phan I'rng theo chuoi sau dudi dang cong thuc cau tao thu gon

• T r o n g phan tir c 6 m o t n d i d o i ( C = C ) v d i C lai hoa sp- tao goc 120", phSng

t r o n g d o c 6 1 lien k^'t a b^n va m o t l i e n ket 7t kern b6n n e n anken dd t h a m

g i a phan irng hon ankan

• N g u y e n tir C k h o n g quay diroc quanh lian ket d d i ( C = C ) l a m xuS't hien d d n g

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 khf, Q C|« l o n g va t r d I6n t d n tai d a n g ran

• N h i e t d d n d n g chay va nhiet d o sdi t u o n g d d i tha'p, t i khd'i h o i n h d , t i n h tan

t r o n g nirdc k e m

• Cac anken t h i r d n g phfln cue (|.i ^ 0 ) va fi,„ > \i„,„„ d o d d cac d d n g phan trans

- anken n d n g chay a nhiet d p cao hon n h u n g l a i sdi d nhiet d d tha'p hon so vdi cac d d n g phan cis tirong I'rng

• 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

L i e n ket n ciia anken k e m ben At hi dut de tao thanh lien ket a v d i cac nguyen tir

khac nen dh t h a m g i a phan I'rng c d n g , phan ihig t r u n g hop 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 :

G o i X la h d n h o p anken va ban d a u , Y la hdn h o p t h u dupc sau phan iJng T a

c d :

• 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 theo t i le m o l 1: 1 t h i

d d la a n k e n

• N e u 2 hay nhieu anken c d n g v d i H2 v d i c u n g hieu suat t h i ta c d the' thay hdn

hop bang c d n g thuc t u o i i g ducmg C - H

nank.n pif = 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

hieu suat

Sffcld chuSiphan li-ng hda hpc Httu ca- Nguyln XuQn Tru&ng

• V i h6n hop X, Y c6 cung s6 mol C, H nSn d6't chay h6n hop A hay B d^u cho

cung ke't qua :

'CO2 va r» sinh ra do d6't X = n^Q va nu r, sinh ra do dot Y ' H, o

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

phan ling dot chay X de ti'nh nco ^ va UH ^

M Y

< 1 (gia sCr

X, Y do o cung dieu kien t°, ap sua't)

h) Cdna halogen (CI Br,)

C„H,„ + X, (dd)

Nhan xet :

• 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

• Khd'i lugng ciia binh dung dung dich brom tang I6n la khoi luong ciia anken

• Neu bai toan cho m6t hay mot s6' hidrocacbon mach ho thuoc ciing day d6ng

dang tac dung voi brom theo ti le mol 1: 1 thi cac hidrocacbon do la anken

• Quy tac Mac-c6p-nhi-c6p : Khi c6ng mot tac nhan bat d6'i H A (axit hoac

nucfc) vao liSn ket d6i (C = C) ciia anken thi san phim chinh dugc tao thanh

do phAn duong ciia tac nhan (H*) gin vao C ciia n6'i d6i mang di6n am

(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 :

• Giai thich quy tac : Do g6'c ankyl day electron lam cho lidn ket 71 bj phan cue,

n6n ion duong dd gdn vao cacbon mang didn am va ngugc lai

• Kha nang phan ling c6ng : H I > HBr > HCl > HF

+ Phan iimg trung hop

CH, polipropilen (PP)

! I''

+ Phan iimg oxi hoa

a) Oxi hda hodn toan :

• Dot chay h6n hop anken + ankin (ankadien) thi n^.^^ > n^^^Q va

i) Oxi hda khon^ hodn toan

17

Nhdri xet: D i r a v a o sir biei 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

nhat mau va c6 ke't tiia mau den xuS't hifen) phan ung nay duoc dung de nhan ra

sir CO mat cua n6'i d6i, nO'i ba

n6'i d6i cho xeton, axit cacboxylic hay CO, tuy theo CTCT cua anken Phan

ling nay dugc dung de' xac dinh vj tri cua n6'i d6i dua vao ca'u tao cua san

ph^m oxi hoa

• Trong cong nghiep ngirofi ta oxi hoa nhe etilen de san xua't C H 3 C H O

t°

+ Phan ling the

• 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 th^ tham gia phan

ling the' boi d o V i du :

• Lien ke't d6i lien : Hai lien ke't d6i of li^n nhau V i du:

C H , = C = CH2 propadien (anlen)

• Lien kd't doi lien hgp: Hai lien ke't d6i b each nhau m6t lien ke't don V i du :

C H 2 = C H - C H = C H 2 CH2=C(CH3)-CH=CH2

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

V f d u : , 2 3 4 5

CH2 = CH - CH2 - CH = CH2 penta - 1,4 - dien

3, B u t a d i e n v a isopren

a) Tinh chat vat li

- Butadien hay divinyl la chat khong mau, c6 mui dac trung, t° = - 4''C

- Isopren hay 2- metylbuta-1,3- dien la cha't long, kh6ng mau, s6i b 34°C

Deu la nhQng chat khdng tan trong nu6c nhirng tan dugc trong cac dung moi huu CO

h) Tinh chat hoa hoc + Phcin ifng cong

• Cong halogen (X2) vd hidrohalogenua (HX)

Butadien cung nhu isopren c6 th^ tham gia phan ling cong X2, H X va thucmg tao ra h6n hgp cac san phslm c6ng- 1,2 va -1,4 6 nhiet d6 tha'p uu tien tao ra

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?

• Trung hgp — 1,4 d^ cho polime c6 tinh dan h6i cao (cao su) nCH,=CH-CH=CH2 —^'^"'"^ ) [ — C H 2 - C H = C H - C H 2 — ] „

19

• M o t phSn CO the t r u n g hcrp - 1 , 2 d^' tao thanh polime k h 6 n g dan h 6 i D i e u nay

iii>'' g i a i t h i c h tfnh d a n h o i k e m cm m 6 t s6' loai cao su t 6 n g hap ,

n C H , = C H - C H = C H , p t°, xt C H 2 C H

-C H = -C H

5 D i e u c h e a n k a d i e n

+ Dieu clie'hiita - 1J - dien

a) D e h i d r o h o a butan hoSc buten a nhi^t d 6 cao (GOO^C) c 6 m a t cha't x u c tac

• T r o n g phan 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

CO ca'u tao thang, g o c hoa t r i 180°

0

• D 6 d a i l i d n ke't b a ra't ngdn (1,19 A ) nSn electron 6 gSn nhan va b i nhan hut

m a n h nen n g u y e n tir C a n6'i ba c 6 d o a m diSn Ion nha't t r o n g cac loai n g u y d n

3

4

+

a)

tir cacbon (^^^^ = c = 3,29) d o d o cac a n k - 1 - i n c6 H l i n h d6ng, d ^ b i dut d ^

d o n g vai t r o tac nhftn t r o n g phan l i n g c6ng hoSc phan ling the'vdi k i m loai

L i e n ke't ba ( C = C ) bao g6m 1 lien ket a va 2 lien ket TT k e m b^n T u y nhien

lien ket 71 t r o n g lien ket ba hcri b^n hon lien ke't 71 trong lien ke't d o i nen phan

iJng c6ng v a o lien ket ba xay ra k h o hem phan ling c6ng vao lien ke't d6i

T i n h c h a t v a t l i ^

• ('1 nhiet d6 thircmg : n = 2 ^ 4 la chaft k h i ''^ '

n = 5 - > 16 la chat l o n g

n > 17 la chat ran 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

H a m l u g n g C, H t r o n g hai h 6 n h o p X va Y la n h u nhau nen k h i giai toan d ^

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

Sff dd chuSi phan irng hda hpc Hihi cff - Nguyen Xuitn Trir&ng

C H C H + HCl ) CH3=CHCI — ^ - C H 2 C H

-Cl Vinyl clorua Poli(vinyl clorua)

CH, = CHCl + HCl CH, - CHCl, ( 1 , 1 — dicloetan)

• Phan ung c6ng vao d6ng dang axetilen tuftn theo quy tac Mac-cop-nhi-cop

CI

cl) Con^ mfdc (hidrat hoa)

• Axetilen + H2O Andehit axetic

vinyl axetat poli(vinyl axetat) (PVA)

+ Phan I'rng dime hoa vii trinie hoa

Khac vdi anken, ankin kh6ng triing hop thanh polime Hai phan tij axetilen c6

th^ c6ng hop vori nhau de' tao thanh vinyl axetilen

2CH = CH ""'f > CH = CH - C = CH

vinyl axetilen

Ba phan tir axetilen c6 the cong hap vdi nhau d6 tao thanh benzen

3CH = CH ^ ^ ^ ^ C,H,

+ Phan I'fng the hang ion kim loai hoa tri I (Ag*, Cu*)

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

nguydn tir kim loai Nhu vay, chi c6 axetilen va cac ank - 1 - in mdri tac dung

diroc vdi dung djch AgNO,/NHi cho ke't tiia mau vang, tac dung vdi dung djch

CuCl/NH, cho ket tiia mau do

Cty TNHH MTVDVVHKhang Vift

Cac phuang trinh hoa hoc : »

CH = CH + 2AgNO, + 2NH3 -> AgC = C A g i + 2NH4NO3

Bac axetilenua (mau vang nhat)

R - C = CH + AgNO, + NH3 R - C = C A g i + NH4NO3

(mau vang nhat)

CH = CH + 2CuCl + 2NH3 -> CuC = CCui + 2NH4CI

D6ng (I) axetilenua (mau do)

R - C = CH + CuCl + NHj -> R-C = CCui + NH4CI < ^

(mau do)

Nhgn xet ;

• 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

• Co the dijng cac phan vrng trfin di nhan bife't axetilen va cac ank - 1- in

• Axetilenua kim loai c6 th6' duac tach ra va phan ling vdi dung dich axit thu

duac axetilen (diing di tach cac chat ra khoi nhau)

Vi du: AgC = CAg + 2 H a -> CH = CH T + 2AgCli

• H6n hap khi X (hidrocabon no, hidrocacbon khdng no, khi khac) di cham qua blnh dung dung dich AgNO,/NH, thu duac hdn hap Y Ta c6

" a n k - 1 - in = Hx " (nx > H y ) Iflbinh ling = ^ a n k - 1 - in

T l k f t lua — Tlmufli ank - I - In

+ Phan I'/ng oxi hoa a) Oxi hoa hoan toan (phan I'mg (hay)

Sadd chuSiphdn li-ng htia hpc HOu ca - Nguyin Xudn Trir&ng

D6't chay h6n hap anken + ankin (ankadien) thi

> n H , 0 va n = n CO- - n

h) Oxi hoa khong hoan roan

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 ^

C 2 H 2 + 2KMn04 + 3 H 2 S O 4 ^ 2C02t + 2MnS04 + K,S04 + 4 H 2 O

SCHj-C^CH + 8KMn04 + 12H,S04 -)•

5 C H 3 C O O H + SCO,! + 8MnO, + 4K,S04 + I 2 H 2 O

Nhan xet : Co th^ diing phan ung lam mat mau dung dich thu6'c tim di nhan

biet cac ankin So vdi anken thi t6c d6 phan utig didn ra cham hon

5 Dieu che

+ Dieu che axetilen

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

2 C H 4

Than da CaCOj - CaO + 3C

500° C

-> than c6'c (C) ) C a O + CO,T

2000° c CaC + CO

16 di^n

CaC, + 2 H , 0 ^ Ca(OH), + C H ^ t '"''^

Nhan xet : 6 nhOng nod c6ng nghidp din khi chua phat trien nguofi ta thuong

di^u che Q H , theo phuong phap trdn

c) TCr C va H2: 2C + H , "^""^"""^ ) C H ,

di$n ' '

d) Tii muoi axetilenua

AgC = CAg + 2HC1 -> C H = C H T + 2AgCl^

CuC = CCu + 2HCl ^ C H s C H T + 2CuCli

+ Dieu chedong dang cua axetilen

a) Dehidio hoa ankan ti/crng I'/ng '

Di tirddn xudt ch,'ra Ag cua ankin va ddn xudt chira halogen cua ankan

• Phircmg phap tang mach cacbon

AgC=C-R+R'Cl -> R'-C=C-R + A g C l i , Phan ling tuong tir doi v6i dSn x u ^ chufa Cu ciia ankin

B BAI TAP C H u 6 l PHAN UNG Bai 1

Sffdb chudipItdn li-ng luiu lt(>c HCru cff ~ Nguyin Xu&n Trir&ng

1,2- dibrompropan Propilen glicol

Hiro'ng dan giai

CH,=CH-CH=CH, > C4H.Br4

Cao su buna

Vinylaxetilen <— C^H,

Hirong dan giai

1 HO-CHo-CH.-COONa + NaOH — ! ^ CHi-CH.-OH + Na.COj