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Bi 1

ANDEHIT
1. KHI NIM 1.1. Andehit l hp cht c nhm fomyl(formil) CHO. 1.2. Cng thc tng qut : R(CHO)n ; CxHy(CHO)n vi iu kin : R c th l gc hidrocacbon, c th l H hoc c th khng c R ; (y+n) l s nguyn dng, chn v (y+n)2n+2. Nu l andehit no, n chc : CnH2n+1CHO hay CmH2mO. 1.3. Qui tc gi tn : Ankan ----------------------> Ankanal ( chn mch chnh di nht cha CHO v C trong nhm CHO c STT 1). Axit Cacboxylic -----------> Andehit Cacboxylic. ( hoc Cacboxylandehit) * Mt s cht tiu biu : H CHO (CH2O) : Metanal ; Andehit fomic ; Fomandehit CH3CHO (C2H4O) : Etanal ; Andehit axetic ; Axetandehit CH3CH2CHO (C2H5CHO , C3 H6O) : Propanal ; Andehit propionic ; Propionandehit CH3CH2CH2CHO (C3H7CHO , C4H8O) : Butanal ; Andehit butiric ; Butirandehit CH3CH(CH3)CHO (C3H7CHO , C4H8O) : 2-Metyl propanal ; Andehit isobutiric ; Isobutirandehit CH3CH2CH2CH2CHO (C4 H9CHO , C5H10O ) : Pentanal ; Andehit n-valeric ; n-Valerandehit CH3CH(CH3)CH2CHO (C4 H9CHO , C5H10O) : 3-Metyl butanal ; Andehit isovaleric ; Isovalerandehit CH3CH2CH2CH2CH2CHO (C5H11CHO , C6 H12O) : Hexanal ; Andehit caproic ; Caprolandehit CH2=CHCHO (C2 H3CHO , C3H4O) : Propenal ; Andehit acrilic ; Acrilandehit ; Acrolein CH2=C(CH3)CHO (C3H5CHO , C4H6O) : 2-Metyl propenal ; Andehit metacrilic ; Metacrilandehit CH3CH=CHCHO (C3H5CHO , C4H6O) : 2-Butenal ; But-2-enal ; Andehit crotonic (trans) ; Crotonandehit (trans) C6H5 CH=CHCHO : 3-Phenyl propenal ; Andehit xinamic (trans) ; Xinamandehit (trans) C6H5 CHO : Phenyl metanal ; Andehit benzoic ; Benzandehit ; Fomyl benzen CH3-C6H4-CHO : p-Toluandehit ; Andehit p-toluic ; p-Metylphenyl metanal HOC-C6H4 OH (2 nhm v tr ortho) : Salixilandehit ; Andehit salixilic ; o-Hidroxi bezandehit HOC - CHO : Etandial ; Andehit oxalic ; Oxalandehit ; Glioxal HOC-CH2-CHO : Propandial ; Andehit malonic ; Malonandehit HOC-CH2-CH2-CHO : Butandial ; Andehit sucxinic ; Suxinandehit HOC-C6H4-CHO (2 nhm v tr ortho) : Andehit o-phtalic ; o-Phtalandehit ; o-difomyl benzen HOC-C6H4-CHO (2 nhm v tr para) : Andehit tereptalic ; Tereptalandehit ; p-difomylbenzen HOC-CH=CH-CHO : (cis) : Andehit maleic ; Maleandehit ; Cis-2-butendial 2. TNH CHT HA HC 2.1. Phn ng cng hiro * Ni i C=O ca anehit (cng nh ca xeton) tham gia c phn ng cng hiro (H2) vi cht xc tc Ni hay Pt hay Pd v un nng to nhm CHOH (nhm chc ru bc 1, CH2OH, i vi anehit; nhm chc ru bc 2, CHOH, i vi xeton).
+1 0 -1

R-CH=O Anehit Cht oxh

+2

+ H2 Cht kh
0

R-CH2OH Ru bc nht
0

R-CO-R' Xeton Cht oxh

+ H2 Cht kh

R-CH(OH)-R' Ru bc 2

* Vit phng trnh phn ng cng H2 : Metanal ; Etanal ; Axeton ; Glioxal ; Andehit malonic

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* iu kin cng hiro vo lin kt i C=O ca anehit, xeton ging nh iu kin cng hiro vo lin kt i C=C, lin kt ba CC. Nhng cng hiro vo C=C, CC d hn so vi C=O, nn anehit, xeton khng no khi cng hiro th hiro cng vo lin kt i C=C, CC ca gc hirocacbon khng no trc ri mi cng vo lin kt i C=O ca nhm chc anehit, xeton sau. Do khi cho anehit, xeton khng no, cng hiro th ta thu c ru bc 1, ru bc 2 no. CnH2n + 2 2k x(CHO)x + (k + x)H2 CnH2n + 2 x(CH2OH)x * Vit phng trnh phn ng cng H2 : Anehit acrilic, Crotonaldehit , Propinal , Metyl vinyl xeton * Trong phn ng andehit cng hiro to ru bc 1 tng ng, th anehit ng vai tr cht oxi ha, cn hiro ng vai tr cht kh. Do ngi ta cn ni dng hiro kh anehit to ru bc 1 tng ng; Hay anehit b kh bi hiro to ru bc mt tng ng. Trong a s trng hp phn ng khc, th anehit th hin tnh kh, nhm chc anehit (CHO) d b oxi ha to thnh nhm chc axit hu c (COOH). 2.2. Phn ng chy CxHy(CHO)0 + (x + y + n )/2 O2 CnH2n +2 x(CHO)x + (3n + x +1)/2 O2 Anehit a chc no mch h CnH2n + 1CHO + (3n + 2 )/2 O2 Anehit n chc no mch h * Ch c anehit n chc no mch h (CTPT c dng Cn H2nO) khi chy mi to s mol H2 O bng s mol CO2. Cc anehit a chc, khng no hoc c vng khi chy u to s mol H2O nh hn s mol CO2. 2.3. Phn ng b oxi ha hu hn bi oxi (ca khng kh) c mui mangan (II) lm xc tc
+1 0 +3

(x + n) CO2 + (y + n)/2 H2O (n + x) CO2 + (n + 1) H2O (n + 1) CO2 + (n + 1) H2O

R-CHO Cht kh

1/2 O2 Cht oxi ha

R-COOH

* Vit phng trnh phn ng v gi tn sn phm : Anehit axetic ; Fomanehit ; Acrolein ; Glioxal ; Bezandehit ; Xinamandehit ; Crotonandehit. 2.4. Phn ng trng gng (trng bc) * Anehit tc dng vi dung dch bc nitrat trong amoniac (dd AgNO3/NH3, thuc th Tollens) to ra kim loi bc (Ag) bm vo thnh bn trong ca ng nghim c mu trng sng c trng. Do ngi ta thng dng phn ng c trng ny nhn bit andehit, cng nh trng lp kim loi bc trn mt thy tinh (to gng soi, bnh thy gi nhit, ). * Trong phn ng ny, anehit ng vai tr cht kh, n b oxi ha to axit hu c tng ng, nhng do trong mi trng baz, amoniac (NH3) c d, nn axit hu c hin din dng mui amoni ca axit hu c. Cn ion bc (Ag+), trong AgNO3/NH3, ng vai tr cht oxi ha, n b kh to ra bc kim loi.
+1 +1 +3 0

R-CHO + 2 AgNO3 + 3NH3 + H2O R-COONH4 + 2 Ag + 2 NH4 NO3 Cht kh Cht oxi ha 1 mol 2 mol * Vit phng trnh phn ng vi : Andehit axetic ; Acrolein ; Anehit oxalic ; Bezandehit ; Andehit metacrilic ; Andehit terephtalic

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* Phn ng trng gng cn c vit theo cc cch khc nh sau: R-CHO + Ag2O R-COOH + 2Ag R-CHO + 2[Ag(NH3)2]OH R-COONH4 + 2Ag + 3NH3 + H2O R-CHO +2[Ag(NH3)2]NO3 + H2O R-COONH4 +2Ag + 2NH4NO3 + NH3 R-CHO + 2[Ag(NH3)2]+ + H2O R-COO- + 2Ag + 2NH4+ + NH3 * Trong hu ht trng hp khi cho anehit n chc tc dng vi dung dch bc nitrat trong amoniac th vi 1 mol anehit n chc, sau khi thc hin phn ng trng gng s thu c 2 mol bc kim loi. Tuy nhin vi anehit fomic (HCHO), mc d l anehit n chc n gin nht, nhng sau khi thc hin phn ng trng gng vi lng d dd AgNO3 trong amoniac th 1 mol anehit fomic thu c 4 mol Ag. Nguyn nhn l trong cu to ca fomanehit coi nh c cha 2 nhm chc CHO, nn vi lng d AgNO3/NH3, n tham gia c phn ng trng gng hai ln v do thu c 4 mol Ag t 1 mol HCHO. H-CHO + 2AgNO3 + 3NH3 + H2O H-COONH4 + 2Ag + 2NH4NO3 H-COONH4 + 2AgNO3 + 3NH3 + H2O NH4O-COONH4 + 2Ag + 2NH4NO3 HCHO + 4AgNO3 + 6NH3 + 2H2O (NH4)2CO3 + 4Ag + 4NH4NO3 Bi tp 1 A l mt hp cht hu c n chc. Ly 672 cm3 hi A (ktc) cho tc dng hon ton vi lng d dung dch bc nitrat trong amoniac, thu c m gam kim loi. em m gam kim loi ha tan ht trong dung dch HNO3 long, thu c 704 ml kh NO 27,3C; 1,4 atm. a. Xc nh CTCT ca A. b. Vit mt phn ng minh ha A c tnh oxi ha v mt phn ng minh ha A c tnh kh. S: HCHO Bi tp 2 A l mt hp cht hu c c cha mt loi nhm chc trong phn t, phn t A cha nhiu hn mt nguyn t cacbon. Ly 210 cm3 hi A ( 136,5C; 608 mmHg cho tc dng hon ton lng d dd AgNO3/NH3, thu c m gam kim loi. em m gam kim loi trn ha tan ht trong dung dch H2SO4 (c, nng), thu c 224 cm3 mt kh c mi hc (ktc). a. Xc nh CTCT ca A. Bit rng dA/H2 < 35. b. Vit phn ng A : b kh bi H2; b oxi ha hon ton v b oxi hu hn bi O2. S: HOC-CHO Bi tp 3 Hn hp H gm hai anehit no mch h A, B. Cho 10,2 gam hn hp H tc dng va vi dung dch AgNO3/NH3 th thu c 64,8 gam Ag. Mt khc, nu ly 12,75 gam hn hp H cho ha hi ht 136,5C, p sut 2 atm th thu c th tch hi l 4,2 lt. a. Xc nh CTCT c th c ca A v B nu s mol ca chng trong hn hp bng nhau. b. Cho hn hp H trn tc dng vi lng d dung dch AgNO3/NH3, thu c dung dch D. Cho dung dch H2SO4 d vo dung dch D thy c to kh thot ra. Xc nh CTCT ng ca A, B. S: a. H-CHO, HOC-CH2-CHO; CH3-CHO, HOC-CHO b. H-CHO, HOC-CH2-CHO

Bi tp 4 Cho 11,76 gam hn hp A gm hai anehit no, mch h bay hi th thu c 4,928 lt ( 27,3C; 1,4 atm). Nu cho lng hn hp A trn tc dng vi lng d dung dch AgNO3/NH3 th thu c 120,96 gam bc kim loi. Nu cho lng hn hp A trn phn ng ht vi H2 th cn dng 8,064 lt H2 (ktc). Xc nh CTCT, c tn v tnh phn trm khi lng mi anehit trong hn hp A. S: 51,02% HCHO; 48,98% HOC-CH2-CHO

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2.5. Phn ng vi ng (II) hiroxit trong dung dch kim, un nng * Andehit b oxi ha bi ng (II) hiroxit trong dung dch kim un nng to thnh axit hu c tng ng, nhng trong mi trng kim nn axit hin din dng mui, cn Cu(OH)2 b kh to thnh ng (I) oxit khng tan, c mu gch.
+1 +2 +3 +1

R-CHO + 2Cu(OH)2 + OH R-COO + Cu2O + 3H2O Cht kh Cht oxi ha Kt ta mu gch * Vit phng trnh phn ng : CH3-CHO + 2Cu(OH)2 + NaOH CH3-COONa + Cu2O + 3H2O CH2=CH-CHO + 2Cu(OH)2 + KOH CH2=CH-COOK + Cu2O + 3H2 O HOC-CHO + 4Cu(OH)2 + 2NaOH NaOOC-COONa + 2Cu2O + 6H2O C6H5-CHO + 2Cu(OH)2 + NaOH C6H5-COONa + Cu2O + 3H2O * n gin ha, ngi ta b qua mi trng kim trong phn ng trn. R-CHO + 2Cu(OH)2 R-COOH + Cu2O + 2H2 O * Thay v dng Cu(OH)2 trong dung dch kim un nng, ngi ta cn dng dung dch Fehling (dung dch hn hp gm ng (II) sunfat, mui tartrat natri kali, xt v nc, CuSO4 NaOOC-(CHOH)2-COOK NaOH H2O) oxi ha anehit to axit hu c tng ng, nhng trong mi trng kim nn axit hin din dng mui, cn Cu2+ b kh to ng (I) oxit c mu gch. Do , c th cn c phn ng c trng ny nhn bit anehit. * Vi 1 mol anehit n chc sau khi phn ng vi Cu(OH)2/OH-, t s thu c 1 mol Cu2O. Ring vi H-CHO, sau khi cho tc dng vi lng d Cu(OH)2/ OH, t s thu c mui cacbonat (mi trng kim) hay kh CO2 thot ra (nu b qua mi trng kim). V trong cu to ca H-CHO coi nh c cha 2 nhm CHO trong phn t. 2.6. Phn ng cng dung dch Natri bisunfit bo ha (NaHSO3 ) * Anehit (R-CHO) v metyl xeton (R-CO-CH3) tc dng c vi dung dch bo ha natri bisunfit (NaHSO3) to hp cht cng bisunfit khng tan, c mu trng. Tng qut, cc xeton khc khng tham gia phn ng ny v chng ngi lp th (cc nhm th qu ln, khng ch bn nhm ln cng lin kt vo mt nguyn t cacbon (C). R-CHO + NaHSO3 R CH(OH)SO3Na * Ngi ta thng dng phn ng c trng ny tch ly ring anehit (R-CHO) cng nh metyl xeton (RCO-CH3 ) ra khi hn hp cc cht hu c. Cho hn hp cc cht hu c c cha anehit hoc metyl xeton tc dng vi dung dch natri bisunfit bo ha th ch c anehit hoc metyl xeton tc dng to hp cht cng khng tan, c mu trng. Sau lc ly sn phm cng bisunfit ny ri cho tc dng vi dung dch axit clohiric (dd HCl) hoc dung dch xt (dd NaOH) s ti to c anehit, cng nh metyl xeton. Bi tp 5 Tch ly ring tng cht ra khi hn hp gm: bezanehit, stiren, toluen v phenol. Bi tp 6 Tch ly ring tng cht ra khi hn hp gm: Axeton, benzen, ru benzylic v n-butyl axetilen.

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3. NG DNG 3.1. Anehit l hp cht trung gian m t iu ch c ru bc 1 (R-CH2OH) v axit hu c (RCOOH) tng ng. * Vit phng trnh cng H2 v O2 : Metanal ; Anehit oxalic; Glioxal ; Anehit oxalic ; Anehit propionic. 3.2. Fomanehit (H-CHO) c dng lm cht st trng (dung dch formol, formalin), iu ch nha phenolfomanehit, glucose, ru metylic, axit fomic, Phenol + Fomandehit Nha phenolfomanehit Fomandehit Glucoz (Glucose) Metanal + Hiro Metanol Anehit fomic + Oxi (KK) Axit fomic 3.3. Thc hin phn ng trng gng, trng c lp kim loi bc vo b mt thy tinh (to gng soi, bnh thy gi nhit, linh kin in t,) 4. IU CH 4.1. Oxi ha hu hn ru bc nht bng CuO, un nng, c anehit. Hay oxi ha hu hn ru bc mt bng oxi ca khng kh c bt kim loi ng lm xc tc, un nng, thu c anehit R-CH2OH + CuO R-CHO + Cu + H2O R-CH2OH + O2 R-CHO + H2O * Vit phng trnh phn ng : Ru etylic ; Metanol ; Ru alylic ; Ru benzylic Benzanehit ; Anehit oxalic 4.2. T axetilen iu ch c anehit axetic CHCH + H2O [CH2 =CH-OH] CH3-CH=O 4.3. T metan iu ch c fomanehit CH4 + O2 H-CHO + H2O Cch khc (qua nhiu giai on): CH4 CH3Cl CH3OH H-CHO Bi tp 7 A l mt anehit n chc, cha mt lin kt i C=C trong phn t, mch h. t chy hon ton a mol A ri cho sn phm chy hp th hon ton vo dung dch nc vi trong c d th thu c 400a gam kt ta. a. Xc nh cc CTCT c th c ca A. c tn cc cht ny. b. A c mch cacbon phn nhnh. Xc nh CTCT ng ca A. Vit phng trnh phn ng ca A vi: - H2, c Ni lm xc tc, un nng - Dung dch natri bisunfit bo ha - Dung dch brom - Dung dch bc nitrat trong amoniac - ng (II) hiroxit trong dung dch xt, un nng - Oxi, c mui Mn2+ lm xc tc - Phn ng trng hp A S: C3H5CHO Bi tp 8 A l mt cht hu c, cha mt loi nhm chc trong phn t, mch h. t chy ht a mol A ri cho sn phm chy hp th ht vo bnh ng nc barit (dung dch Ba(OH)2) d th thu c 788a gam kt ta, khi lng bnh

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tng 212a gam. Nu cho a mol A tc dng vi lng d dung dch bc nitrat trong amoniac th thu c 432a gam bc kim loi. a. Xc nh cc CTCT c th c ca A. b. A c cu to mch thng, cc nhm ln xa nhau nht. Xc nh CTCT ng ca A. c tn A. Vit phng trnh phn ng ca A vi: - Kh hiro c Nicken lm xc tc, un nng - Nc brom - Cu(OH)2, t - Ag2O/NH3 - O2, Mn2+ - Phn ng oxi ha hon ton A bi CuO, un nng, to ra cc cht v c - Phn ng trng hp A S: A: Trans-butenial Bi tp 9 Thm 58 gam B vo 200 gam dung dch 22% ca mt anehit n chc A (B l ng ng k tip sau A), c dung dch D. Ly 101t dung dch D cho tc dng ht vi dung dch bc nitrat trong amoniac th thu c 43,2 gam Ag. a. Tnh nng % ca A v B trong dung dch D. b. Xc nh CTCT ca A, B. Bit rng A c cha nhiu hn 1 nguyn t Cacbon trong phn t. S: 17,05%A; 22,48%B CH3CHO; CH3CH2CHO Bi tp 10 X, Y l hai anehit n chc, khng no, u cha mt lin kt i C=C, mch h, hn km nhau mt nhm metylen trong phn t. Cho 8,4 gam X vo 300 gam dung dch c ha tan Y nng 2,8%, thu c dung dch D. Cho dung dch D tc dng ht vi dung dch AgNO3 trong NH3, thu c 58,32 gam Ag. a. Tnh nng phn trm ca X, Y trong dung dch D. b. Xc nh CTCT ca X, Y. Bit rng Y c mch cacbon phn nhnh. c tn X, Y. S: 2,72%% X; 2,72% Y; X: Acrolein; Y: Anehit metacrilic Bi tp 11 A l mt anehit n chc. Ly 0,2 mol A cho tc dng hon ton vi lng d dung dch AgNO3 trong NH3 th thu c 86,4 gam kim loi. a. Xc nh A. b. Ly 10 gam dung dch A c nng 36% em oxi ha bng O2 , c mui Mn2+ lm xc tc, thu c dung dch B. Cho lng dung dch B ny tc dng hon ton vi lng d dd AgNO3/NH3 th thu c 30,24 gam Ag. Tnh hiu sut phn ng oxi ha A, bit rng A b oxi ha ch to ra axit hu c tng ng. S: A: H-CHO; HS: 83,33% Bi tp 12 A l mt anehit n chc. Ly 0,01 mol A cho tc dng hon ton vi 100 ml dung dch AgNO3 1M trong amoniac. Cho lng d dung dch NaCl vo dung dch thu c sau phn ng trng bc th thu c 8,61 gam kt ta trng. a. Xc nh A. b. Ly 7,5 gam dung dch A nng 20% em oxi ha bng O2 nhm thu axit hu c tng ng, thu c dung dch B. Cho lng d dd AgNO3/NH3 vo dch B, sau khi kt thc phn ng, ly kim loi thu c em ha tan ht trong dung dch HNO3 m c th thu c 2,688 lt mt kh mu nu duy nht (ktc). Tnh hiu sut phn ng oxi ha A bng O2. Tr phn ng oxi ha A bng oxi, cc cc phn ng khc u c hiu sut 100%. S: H-CHO; 80%

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Bi tp 13 X l mt cht hu c. t chy hon ton 3,6 gam X thu c CO2 v H2O. Cho sn phm chy hp th ht vo bnh ng dung dch Ba(OH)2, khi lng bnh tng 7,44 gam. Trong bnh c 15,76 gam kt ta. Nu un nng dung dch trong bnh, thy to thm 3,94 gam kt ta na. a. Xc nh CTPT, CTCT v c tn X. Bit rng CTPT ca X cng l cng thc n gin ca n. b. T X vit cc phn ng iu ch mi hai (12) este n chc no, khng no m s nguyn t cacbon trong phn t nh hn 5. Cc cht v c, xc tc coi nh c sn. S: H-CHO Bi tp 14 X l mt cht hu c. t chy m gam X, cn dng 13,44 lt khng kh (ktc) (khng kh cha 20% kh oxi theo th tch). Cho sn phm chy (gm CO2 v H2O) hp th ht vo bnh ng 1,2 lt dung dch Ba(OH)2 0,1M, khi lng bnh tng 8,48 gam. Dung dch trong bnh Ba(OH)2 gim 7,28 gam so vi khi lng dung dch trc khi hp th sn phm chy. a. Tnh m. b. Xc nh CTPT ca X. c. Cho bit X cha mt loi nhm chc, X tc dng dung dch Fehling to kt ta mu gch. Xc nh CTCT v c tn X. d. Bng nm (5) phn ng iu ch nm cht hu c cha mt loi nhm chc (ch gm cc nguyn t C, H, O). Cc cht v c, xc tc thch hp c sn. S: m = 4,64g HOC-CHO Bi tp 15 (B TSH mn Ha hc) A, B l cc hp cht hu c trong phn t ch cha mt trong cc nhm chc OH, - CHO v COOH. Cho 24,3 gam hn hp cha A v B tc dng vi 200 ml dung dch AgNO3 2,5 mol/l trong amoniac, lc tt c Ag+ b kh ht thnh Ag kim loi. Ly cc mui amoni to thnh cho tc dng ht vi dung dch H2SO4 v chng ct ly hn hp axit hu c. Cho Na2CO3 t t vo hn hp axit n ht thot kh th thu c 4,923 lt CO2 ( 210C v 744,8 mmHg) v dung dch cha 34,9 gam hn hp hai mui ca hai axit hu c. a. Tm CTPT v CTCT ca A, B. b. Tnh % khi lng ca A, B trong hn hp ban u. S: 54,32% CH3-CHO; 45,68% CH3-CH2-COOH Bi tp 16 Hn hp A gm X v Y l hai hp cht hu c n chc m trong phn t c cha mt trong cc nhm chc: ru (-OH), anehit (CHO), axit (COOH) v phn t cha nhiu hn mt nguyn t cacbon. Cho 15,72 gam hn hp A tc dng vi 100 ml dung dch AgNO3 2M trong amoniac. Tt c Ag+ b kh ht to kim loi, amoniac cn d trong mi trng. Cho cc mui amoni thu c cho tc dng ht vi dung dch H2 SO4 th thu c axit hu c tng ng. Cho Xa (Soda, Na2CO3) t t vo hn hp axit hu c trn cho n ht to kh th thu c 2,8 lt CO2 (ktc) v dung dch thu c c cha 21,7 gam hn hp hai mui ca ca hai axit hu c. a. Xc nh CTPT, CTCT ca A v B. b. Tnh % khi lng ca X, Y trong hn hp A. S: 57,25% CH3COOH; 42,75% CH2=CH-CHO

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