T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Kin thc trng tm

Chng 1. ESTE - LIPIT
I. Kin thc trng tm - Nm vng cng thc cu to ca este (phn gc, phn chc) tnh cht ca este. - Hiu cc khi nim lipit, cht bo, x phng, cht ty ra tng hp. - Bit r cc ng dng ca este, cht bo, cht git ra - Hiu r mi lin h gia hirocacbon v cc dn xut ca hirocacbon. A. Este 1. Cu to phn t ca este n chc
R C O O R'

(lin kt trong nhm C=O bn, nn kh cho phn ng cng) 2. Gi tn Tn este = tn gc hirocacbon + tn gc axit 3. Tnh cht Cc este thng l cc cht lng d bay hi, t tan trong nc, c mi thm c trng. Phn ng thy phn : - Mi trng axit :

R COO R '+ H OH R COOH + R ' OH - Mi trng kim : (phn ng x phng ho)

H + ,t o

R COO R ' + OH R COO + R ' OH

Ch : - Khi thy phn cc este ca phenol :
R COO C 6 H 5 + 2NaOH R COONa + C 6 H 5OH + H 2 O - Khi thy phn mt s este c bit :
to

to

17

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

R COO CH = CH 2 + NaOH R COONa + CH 3 CH = O

to

R' R-COO-C=CH2 + NaOH

Phn ng kh :

to

R-COONa + R'-C-CH3 O

R C O O

R'

LiAlH4

R CH2 OH + R' OH

Tnh cht khc : cc este c gc hirocacbon khng no c th cho phn ng cng (vi hiro, halogen...) v phn ng trng hp ti gc hirocacbon.

4. iu ch
2 4 RCOOH + ROH RCOOR H2O (Mun cn bng ho hc chuyn dch theo chiu to ra este, nn ly d axit hoc ancol v chng ct tch este ra khi hn hp). Phenol khng cho phn ng este ho vi cc axit, ch cho phn ng este ho vi cc anhirit axit (hay clorua axit)

H SO c,t o

C 6 H 5 OH + R C O C R R COO C 6 H5 + R COOH || || O O

to

5. ng dng
Este dng lm dung mi, thu tinh hu c, cht do, keo dn, cht ho do, dc phm. Mt s este c mi thm hoa qu c dng trong cng nghip thc phm v m phm.

B. Lipit 1. Khi nim

Lipit l cc hp cht hu c phc tp gm : cht bo, sp, sterit, photpholipit... Trong chng trnh ph thng ch xt cht bo. Cht bo l trieste ca glixerol vi cc axit monocacboxylic c mch C di (thng C12 ) khng phn nhnh, gi chung l triglixerit.

2. Cu to phn t ca cht bo :

18

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

CH2 CH
1 2 3

OOC OOC

R1 R2 R3

CH2 OOC

(R , R , R l cc gc hirocacbon no hay khng no, ging nhau hay khc nhau) l este 3 chc nn c cc tnh cht nh este.

3. Tnh cht a) Tnh cht vt l Cht bo rn (m) : cha ch yu cc gc axit bo no. Cht bo lng (du) : cha ch yu cc gc axit bo khng no. Khng tan trong nc, d tan trong dung mi hu c. b) Tnh cht ho hc Phn ng thy phn trong mi trng axit : (chm, thun nghch) glixerol v cc axit bo. Phn ng thy phn trong mi trng kim : (nhanh, mt chiu) glixerol v mui natri hay kali ca cc axit bo (l x phng). Phn ng hiro ho : chuyn cht bo lng thnh cht bo rn V d : CH2 OOC C17H33 CH2 OOC C17H35

CH CH2

OOC C17H33 + H2 OOC C17H33

Ni,t

CH CH2

OOC C17H35 OOC C17H35

Triolein (lng)

Tristearin (rn)

Phn ng oxi ho : Cht bo lu trong khng kh, th cc gc axit khng no b oxi ho chm to thnh cc anehit c mi kh chu. Ch : + Ch s x phng ho l s miligam KOH cn dng x phng ho triglixerit v trung ha axit bo t do c trong 1 gam cht bo. + Ch s axit ho l s miligam KOH cn dng trung ha axit bo t do c trong 1 gam cht bo.

4. Vai tr v ng dng
S chuyn ho cht bo trong c th

19

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Cht bo

rut non

axit bo thnh rut glixerol

t bo

CO2 nng lng m m

Cht bo

d tr

ng dng : Dng sn xut x phng, glixerol, cht do, m phm, thuc n, thc phm...

C. Cht git ra
Khi nim Phn loi Cht git ra l cc cht khi dng cng vi nc th lm sch cc vt bn trn cc vt rn m khng phn ng vi cht bn X phng Cht git ra tng hp + + Mui ankyl sunfat, ankyl Mui Na v K ca cc axit bo sunfonat hay ankyl benzensunfonat u a nc ui k nc u a nc ui k nc

c im cu to u im

t gy hi cho da, khng gy Dng c trong nc cng v nhim mi trng (b vi khun t to kt ta vi Ca2+, Mg2+ phn hy) Nhc Khng dng c trong nc cng Khng b vi khun phn hy 2+ 2+ im gy nhim mi trng v to kt ta vi Ca , Mg * Cht ty mu : c phn ng ho hc vi cht bn.
Thng l cc cht c tnh oxi ho mnh nh : nc Gia-ven, nc clo, kh SO2,...

D. Mi lin h gia hirocacbon v cc dn xut 1. Mi lin h gia cc loi hirocacbon

Chuyn hirocacbon no thnh khng no v thm : + Phng php hiro ho : C n H 2n 6 C n H 2n +2 C n H 2n C n H 2n 2
(aren) (ankan) (anken) (ankaien) xt,t o 4H 2 xt,t o H2 xt,t o H2

+ Phng php cracking : C n H 2n +2 C x H 2x +2 + C y H 2y (x + y = n) Chuyn hirocacbon khng no v thm thnh no :

xt,t o

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T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

2 2 R C C R R CH = CH R R CH 2 CH 2 R o o

+H Pd / PbCO3 ,t

+H Ni,t

C n H 2n 6 + 3H 2 C n H 2n
aren

Ni,t o

xicloankan

2. Mi lin h gia hirocacbon v dn xut cha oxi a) Chuyn hirocacbon trc tip thnh dn xut cha oxi Oxi ho hirocacbon iu kin thch hp : 5 xt,t o R CH 2 CH 2 R ' + O2 R COOH + R ' COOH + H 2 O 2 Hirat ho ankin :
CH CH + H 2 O CH3 CH = O Cc ankin khc khi cng nc to ra xeton (ch quy tc Maccopnhicop) : R H C R ' + H 2 O R C CH 2 R ' || O b) Chuyn ho thng qua dn xut halogen
2 R H R X R OH o o

Hg2 + ,H + ,t o

Hg2 + ,H + ,t o

+X as(t )

+ NaOH H 2 O,t

2 Ar H Ar X Ar ONa Ar OH o

+X Fe

+ NaOH p,t

H+

c) Chuyn ancol v dn xut halogen thnh hirocacbon Tch nc t ancol thnh anken : ch quy tc Zaixep R' H 2 SO 4 ,170o C R CH CH C R CH CH C R" H OH H H

R' R"

+ H2O

Tch HX t dn xut halogen thnh anken : ch quy tc Zaixep R' R' KOH R CH CH C R CH CH C + HX o C 2 H5OH,t R" R" H X H H

d) Chuyn ho gia cc dn xut cha oxi

Phng php oxi ho (+ CuO, O2, [Ag(NH3)2]OH, Cu(OH)2 , to) : + Oxi ho nh ancol bc 1 c anehit (oxi ho mnh c axit)

21

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

R CH 2 OH + CuO R CH = O + Cu + H2O R CH = O + H2O2 R COOH + H2O + Oxi ho nh ancol bc 2 c xeton (oxi ho mnh c axit)
t R CH R ' + CuO R C R ' + Cu + H2O || | O OH
4 R C R ' R COOH + R ' COOH || O o

to

H+

KMnO ,H + ,t o

Phng php kh (+ H2, LiAlH4) : Vi anehit v xeton : dng cht kh l H2 + Kh anehit c ancol bc 1 : R CH = O + H2 R CH 2 OH + Kh xeton c ancol bc 2 :
Ni,t o

R C R ' + H2 R CH R ' || | O OH Vi axit v este : dng cht kh l LiAlH4 + Kh axit thnh ancol bc 1 :
4 R COOH R CH 2 OH

Ni,t o

LiAlH

+ Kh este thnh ancol :

4 R COO R R CH 2 OH + ROH

LiAlH

Este ho v thy phn este :

2 4 R COOH + ROH R COO R + H2O

H SO ,t o

R COO R + H O H R COOH + ROH

H + ,t o

R COO R + NaOH R COONa + ROH

3. Cc phng php tng v gim mch C khi iu ch a) Phng php gim mch C Phng php cracking :

to

22

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

C n H 2n +2 C x H 2x +2 + C y H 2y (x + y = n)
ankan anken

xt,t o

Gim 1 C : R COONa + NaOH R H + Na 2 CO3 2R COONa + 2NaOH R H + Na 2 CO3 + K 2 CO3

CaO,t o CaO,t o

b) Phng php tng mch C T dn xut halogen (t hirocacbon iu ch dn xut halogen) :

2 2 4 R X + Mg R Mg X R COOH 3 R X + KCN R CN R COOH T anehit v xeton :

ete

1)CO , 2)H SO

xt,t o

H O + ,t o

H3O ,t R CH O + H CN R CH OH R CH OH

CN CN
R C
R' + H CN R C

COOH COOH
R'
3 R C

H O + ,t o

R'

O OH OH (T cc axit trn, dng LiAlH4 kh thnh ancol tng ng, ri tch nc c hirocacbon) c) K nng Vit c cc phng trnh ho hc biu din mi lin h gia cc cht hu c. Xc nh c cng thc cu to cc cht hu c.

II. Bi tp p dng A. Trc nghim khch quan 1.

Trong 4 este c cng thc phn t : C3H4O2, C4H6O2, C3H6O2, C4H8O2. Este khi b thu phn to ra hai cht c kh nng tham gia phn ng trng gng l A. C3H4O2 C. C4H6O2 B. C3H4O2 v C4H6O2 D. C3H6O2 v C4H8O2

23

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

2.

Phenyl axetat c iu ch trc tip t A. axit axetic v phenol. B. anhirit axetic v phenol. C. axit axetic v ancol benzylic. D. anhirit axetic v ancol benzylic.

3.

X phng ho este A c cng thc phn t C5H8O4 thu c hai ancol l metanol v etanol. Axit to nn A l A. axit axetic. B. axit malonic (axit propanioic). C. axit oxalic (axit etanioic). D. axit fomic. Cng thc tng qut ca mt este to bi axit no, n chc, mch h v ancol khng no c mt lin kt i, n chc, mch h l A. CnH2n2O2 C. CnH2nO2 B. CnH2n2kO2 D. CnH2n1O2

4.

5.

Cho s chuyn ho sau : C2H5OH X Y CH3COOCH3. X, Y ln lt l A. CH3CHO, CH3COOH C. CH3CHO, CH3CH2OH B. CH3COOH, CH3CHO D. C2H4, CH3CH2OH

6.

t chy hon ton este X thu c n CO2 = n H 2O . Vy X l este A. n chc, mch h, c mt lin kt i C=C. B. no, n chc, mch h. C. no, hai chc, mch h. D. n chc, mch h, c mt lin kt i C=C hay n chc, mt vng no. Cho s chuyn ho : A B CH4 Cc cht phn ng vi nhau theo t l mol 1 : 1. Cng thc khng ph hp vi cht A l A. CH3OOCCH3. C. CH3COONH4. B. CH3COOH. D. HCOOCH3.
+ NaOH + NaOH

7.

24

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

8.

Sp xp theo chiu tng dn v nhit si ca cc cht (1) C3H7COOH, (2) CH3COOC2H5 v (3) C3H7CH2OH, ta c th t : A. (1), (2), (3). B. (2), (3), (1). C. (1), (3), (2). Cho dy chuyn ho :
+ HCN

D. (3), (2), (1).

+ H O,H +
H SO ,180o C

9.

2 2 4 CH3CHO A B D. Cht D l

A. CH3CH2COOH. C. CH2=CHCN.

B. CH2=CHCOOH. D. CH2=CHCH2OH.

10.

Khi thu phn hon ton 265,2 gam cht bo bng dung dch KOH thu c 288 gam mt mui kali duy nht. Tn gi ca cht bo l A. glixerol tristearat (hay stearin). B. glixerol tripanmitat (hay panmitin). C. glixerol trioleat (hay olein). D. glixerol trilinoleat (linolein). Nhn nh no sau y ng ? A. Phn ng ca cht bo vi dung dch kim l phn ng x phng ho. B. Phn ng ca glixerol vi HNO3 c to ra glixerol trinitrat l phn ng este ho. C. C th dng cht git ra tng hp git o qun trong nc cng. D. X phng lm sch vt bn v c phn ng ho hc vi cht bn. Ch s axit l s miligam KOH cn dng trung ha cc axit bo t do c trong 1 gam cht bo. trung ha 14 gam cht bo cn 15 mL dung dch KOH 0,1 M, ch s axit ca cht bo ny l A. 5,6. B. 6. C. 7. D. 14. Nhn nh no sau y ng ? A. X phng v cht git ra tng hp c c ch git ra khc nhau. B. X phng v cht git ra tng hp u c cu to "u a nc" v "ui di k nc". C. Cht git ra tng hp v cht ty mu c c ch lm sch ging nhau. D. X phng v cht git ra tng hp u gy nhim mi trng v khng b phn hy theo thi gian.

11.

12.

13.

25

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

14.

15.

Tng s ng phn cu to ca hp cht n chc c cng thc phn t C3H6O2 l A. 1. B. 2. C. 3. D. 4. un nng hn hp gm 9 gam axit axetic vi 4,6 gam ancol etylic c mt xc tc H2SO4 c. Sau phn ng thu c 6,16 gam este. Hiu sut ca phn ng este ho l A. 52,20%. B. 46,67%. C. 70,00%. D. 45,29%.

B. Trc nghim t lun Cu 1 : a) Ti sao cht bo kh tan trong nc nhng d tan trong xng, du hay benzen ? b) Dng cht git ra tng hp git qun o trong nc cng th c hao ph cht git ra tng hp khng ? c) C th dng nc gia ven thay th x phng hay cht git ra tng hp trong vic lm sch qun o khng ? Cu 2 :
Vit v gi tn cc ng phn este c cng thc phn t C4H6O2. Cu 3 : Vit cc phng trnh ho hc to thnh este khi cho : a) Axit no n chc, mch h phn ng vi ancol no, a chc, mch h. Cho v d vi axit axetic v etylen glicol. b) Axit khng no (c 1 ni i) n chc, mch h phn ng vi ancol no, a chc, mch h. Cho v d vi axit acrylic v glixerol. c) Axit no a chc, mch h phn ng vi ancol khng no (c 1 ni i), n chc, mch h. Cho v d vi axit oxalic v ancol anlylic. Cu 4 : Vit cc phng trnh ho hc thc hin dy chuyn ho sau : a) C4H10 X CH3COOCH3 C2H5OH X Y poli(vinyl axetat) b) Oleinnatri oleataxit oleicaxit stearicnatri stearatcanxi stearat. c) Toluen X benzen cumen Y propan-2-ol Z anlyl clorua T propan-1-ol

26

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Cu 5 : Hon thnh cc phn ng sau :

a) HCOOCH=CH2 + NaOH b) CH3COOH + ?
CH3COOC(CH3)=CH2
to

c) CH3COOC6H5 + 2NaOH d) C6H5OH + (CH3CO)2O e) C6H5COOCH=CHCl + NaOH

Cu 6 : T propan v cc cht v c cn thit hy vit phng trnh ho hc iu ch cc hp cht sau : a) Axit isobutiric ; b) Poliacrylic Cu 7 : Thy phn este E n chc thu c axit mch h c nhnh X v ancol Y. Cho Y qua CuO t nng th thu c sn phm hu c Z. Cho 0,1 mol Z phn ng hon ton vi dung dch AgNO3 trong NH3 th c 43,2 gam Ag. T khi hi ca E i vi He l 4. Hy xc nh cng thc cu to, nu ng dng ch yu ca E v vit cc phng trnh ho hc xy ra. Cu 8 : x phng ho hon ton 50 gam cht bo c ch s axit l 10 v cha 5% tp cht tr cn dng 6,5 gam NaOH. Tnh khi lng glixerol v x phng thu c. Cu 9 :
t chy hon ton 0,1 mol cht bo X ngi ta thu c 5,7 mol kh CO2 v 5,2 mol H2O. Khi thy phn 0,1 mol cht bo X ngi ta thu c 3 axit A, B, C khng phi ng phn ca nhau. Bit rng t B hay C c th iu ch A ch bng mt phn ng. Xc nh cng thc ca X. Cu 10 : Cho 1 mol axit axetic tc dng vi 1 mol ancol etylic n khi phn ng t trng thi cn bng th c 0,667 mol este to thnh. Trong cng iu kin nhit trn : a) Nu xut pht t 0,5 mol axit axetic v 2 mol ancol etylic th c bao nhiu mol este to thnh khi phn ng t ti trng thi cn bng ?

27

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

b) Nu xut pht t 1 mol etyl axetat v 2 mol nc, hi khi phn ng t trng thi cn bng th c bao nhiu mol este tham gia phn ng ?

III. Hng dn gii p n A. Trc nghim khch quan

1 B 2 B 3 C 4 A 5 A 6 B 7 D 8 B 9 B 10 C 11 C 12 B 13 B 14 C 15 C

B. Trc nghim t lun Cu 1 : a) Cht bo l trieste ca glixerol v cc axit bo nn phn t c lin kt ho hc t phn cc do t tan trong cc dung mi phn cc mnh nh nc v d tan trong cc dung mi t phn cc nh xng, du hay benzen. b) C th dng bt git git qun o trong nc cng v bt git l mui + + ankyl sunfat, ankyl sunfonat hay ankyl benzensunfonat ca Na hay K , cc 2+ mui ny khi ha tan vo nc s t to kt ta vi cc cation Mg hay 2+ Ca , nn nc cng gn nh khng nh hng n vic lm sch qun o ca bt git. c) Khng th dng nc Gia-ven thay th x phng hay bt git trong vic lm sch qun o v nc Gia-ven cho phn ng ho hc vi cht bn v do cng cho phn ng vi vi si v lm hng vi si. Cu 2 : 4.2 + 2 6 +v= =2 2 c 1 lin kt nhm C=O v mch cacbon ca gc hirocacbon hay gc axit c 1 lin kt hay vng.
CH2=CHCOOCH3 ; metyl acrylat HCOOCH2CH=CH2 anlyl fomiat CH3COOCH=CH2 ; vinyl axetat

28

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

HOO C H C

H CH 3

HOO C H C

CH3 HCOO H CH

CH CH xiclopropyl fomat

trans-prop-1-en-1-yl fomat cis-prop-1-en-1-yl fomat

Cu 3 :
2 4 a) aCnH2n+1COOH + CmH2m+2a(OH)a

H SO c, t o

(CnH2n+1COO)aCmH2m+2a + aH2O
2 4 VD : 2CH3COOH + C2H4(OH)2 (CH3COO)2C2H4 + 2H2O 2 4 b) aCnH2n1COOH + CmH2m+2a(OH)a

H SO c, t o

H SO c, t o

(CnH2n1COO)aCmH2m+2a + aH2O
2 4 VD : 3CH2=CHCOOH + C3H5(OH)3

H SO c, t o

(CH2=CHCOO)3C3H5 + 3H2O
2 4 c) CmH2m+2a(COOH)a + aCmH2m1OH

H SO c, t o

CmH2m+2a(COOCmH2m1)a + aH2O
2 4 VD : (COOH)2 + 2CH2=CHCH2OH

H SO c, t o

(COOCHCH=CH2)2 + 2H2O

Cu 4 :
a) 2C4H10 + 5O2 4CH3COOH + 2H2O
2 4 CH3COOH + CH3OH CH3COOCH3 + H2O 4 CH3COOCH3 C2H5OH + CH3OH

xt,t o

H SO c, t o

LiAlH

C2H5OH + O2 CH3COOH + H2O CH3COOH + CH CH CH3COOCH=CH2

xt,t o
o

enzim,t o

nCH2=CH OOCCH3

xt, t , p

CH2

CH OOCCH3 n

29

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

b) C17H33COO CH2

CH2 OH OH CH2 OH
+ Na2SO4 + H2O
Ni,t
o

C17H33COO CH + 3NaOH 3C17H33COONa + CH

C17H33COO CH2
2C17H33COONa + H2SO4 2C17H33COOH C17H33COOH + H2 C17H35COOH C17H35COOH + NaOH C17H35COONa
to

C17H35COONa + CaCl2 Ca(C17H35COO)2 + 2NaCl

c) C6H5CH3 + 2KMnO4 C6H5COOK + KOH + 2MnO2 + H2O (X)

2C6H5COOK + 2NaOH 2C6H6 + Na2CO3 + K2CO3 C6H6 + CH3CH=CH2 C6H5CH(CH3)2
2 2 4 C6H5CH(CH3)2 C6H5OH + CH3COCH3 (Y)

CaO,t o

H + ,t o

+ O ,H SO ,t o

CH3COCH3 + H2 CH3CHOHCH3
2 4 CH3CHOHCH3 CH3CH=CH2 + H2O (Z)

Ni,t o

H SO c,180o C

CH3CH=CH2 + Cl2 CH2=CHCH2Cl + HCl CH2=CHCH2Cl + NaOH CH2=CHCH2OH + NaCl (T) CH2=CHCH2OH + H2 CH3CH2CH2OH
Ni,t o to

500o C

Cu 5 :
a) HCOOCH=CH2 + NaOH c) CH3COOC6H5 + 2NaOH d) C6H5OH + (CH3CO)2O

xt,t
o

HCOONa + CH3CHO CH3COONa + C6H5ONa + H2O

to

b) CH3COOH + CH CCH3 CH3COOC(CH3)=CH2

CH3COOC6H5 + CH3COOH

e) C6H5COOCH=CHCl + NaOH C6H5COONa + ClCH2CHO

30

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Ch : nguyn t Cl gn vo C c lai ho sp2 khng cho phn ng th vi NaOH khi khng c p sut cao nn sn phm khng c cht HOCH2CHO. Cu 6 : a) iu ch axit isobutiric
CH3CH2CH3 CH3CH=CH2 + H2 CH3CH=CH2 + H2O CH3CHOHCH3 CH3CHOHCH3 + CuO CH3COCH3 + Cu + H2O CN
to H+ , to xt, t o

H3C C O CN H3C C

CH3 + H CN H3C

C OH

CH3

COOH
CH3 H3C
H3O + ,t o

C OH

CH3
02.

OH COOH
H3C C OH
CH2 C CH3 COOH + H2
H SO c

2 4 CH3 CH2 C 180 o C

COOH + H2O

CH3
N i, t
o

CH3

CH CH3

COOH

b) iu ch poliacrylic

CH3CH2CH3 CH2=CH2 + CH4

2CH2=CH2 + O2 2CH3CHO CH3CHO + HCN CH3CH(OH)CN
3 CH3CH(OH)CN CH3CH(OH)COOH 2 4 CH3CH(OH)COOH CH2=CHCOOH + H2O

xt,t o

xt,t o

xt,t o

H O+ , t o

H SO c,180o C

n CH2 CH COOH

xt,t o ,p

CH2

CH COOH n

31

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Cu 7 :
a) E l este n chc nn c cng thc tng qut CxHyO2 Ta c 12x + y + 32 = 100 y = 68 12x V 0 < y 2x +2 0 < 68 12x 2x +2 4,7 < x < 5,6 x = 5 v y = 8

Cng thc phn t ca E l C5H8O2 ancol Y (n chc) + CuO Z (n chc)

v 0,1 mol Z (n chc) + AgNO3 trong NH3 to ra 0,4 mol Ag

Z ch c th l HCHO Y l CH3OH gc axit X l C3H5COO

V axit c nhnh v mch h nn CTCT ca axit l CH2=C(CH3)COOH. Vy cng thc ca A l CH2=C(CH3)COOCH3 (metyl metacrylat). Cc phng trnh ho hc :
CH2=C(CH3)COOCH3 + H2O CH2=C(CH3)COOH + CH3OH
H + ,t o

CH3OH + CuO HCHO + Cu + H2O HCHO + 4[Ag(NH3)2]OH (NH4)2CO3 + 4Ag + 6NH3 + 2H2O
to

to

ng dng : Trng hp E ta c mt loi polime rt thng dng l thy tinh hu c.

xt, p, t
o

COOCH3 CH2 C CH3 n

CH2

C COOCH3 CH3

Cu 8 :
mNaOH trung ha axit t do = 50.10.10-3 = 0,5 gam => m NaOH thy phn cht bo = 6,5 0,5 = 6 gam 6 nNaOH thy phn cht bo = = 0,15 mol 40 100 5 Khi lng cht bo b thy phn = 50 = 47,5 gam 100 (RCOO)3C3H5 + 3NaOH 3RCOONa + C3H5 (OH)3

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T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Theo phn ng : n glixerol =

1 1 n NaOH = 0,15 = 0,05 mol 3 3 m glixerol = 0,05.92 = 4,6 gam p dng nh lut bo ton khi lng : mx phng = mcht bo + mNaOH - mglixerol = 47,5 + 6 4,6 = 48,9 gam

Cu 9 :
t CTPT cht bo X l CxHyO6 y y CxHyO6 + (x+ 3 )O2 xCO2 + H2O 4 2 y 1 x 2 0,1 5,7 5,2
x = 57 v y = 104 X c CTPT l C57H104O6

57 2 + 2 104 =6 2 3 lin kt cho 3 nhm COO cn 3 lin kt cho 3 gc axit.

s lin kt =

Gc ca glixerol l C3H5 3 gc axit c s nguyn t cacbon l 54 v s nguyn t hiro l 99. T B hay C iu ch cht A ch bng mt phn ng A, B, C c cng s 54 nguyn t cacbon l : = 18 . 3 V A, B, C khng phi ng phn ca nhau nn s nguyn t hiro cc gc hiro cacbon phi khc nhau

A l C17H35COOH ; B l C17H33COOH v C l C17H31COOH.

C17H35COO CH2 Cng thc cht bo l :

Cu 10 :

C17H33COO CH C17H31COO CH2

33

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

2 4 CH3COOH + CH3OH CH3COOCH3 + H2O Ban u : 1 1 0 0 Phn ng : 0,667 0,667 0,667 0,667 TTCB : 1 0,667 1 0,667 0,667 0,667

H SO c, t o

Kc =

[este] [H 2 O] 0,6672 = =4 [axit] [ancol] (1 0,667)2

H SO c, t o

a) Gi x l s mol axit phn ng :

2 4 CH3COOH + CH3OH CH3COOCH3 + H2O Ban u : 0,5 2 0 0 Phn ng : x x x x TTCB : 0,5 x 2x x x

Vi Kc c tnh theo trn : 4= x2 (0, 5 x)(2 x)

Gii phng trnh ta c x = 0,465 mol s mol este to thnh l 0,465 mol b) Gi x l s mol este phn ng
2 4 CH3COOCH3 + H2O CH3COOH + CH3OH Ban u : 1 2 0 0 Phn ng : x x x x TTCB : 1x 2x x x [axit] [ancol] K 'c = [este] [H 2 O]

H SO c, t o

V cng iu kin nhit trn nn hng s cn bng ca phn ng nghch 1 1 vi phn ng ca cu a): K 'c = = Kc 4 1 x2 = 4 (1 x)(2 x) Gii phng trnh ta c x = 0,457 mol S mol este tham gia phn ng l 0,465 mol.

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T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Chng 2. CACBOHIRAT
I. Kin thc trng tm
Nm vng cu trc phn t ca cc hp cht cacbohirat vit CTCT ca cc hp cht dng : mch h v mch vng. Glucoz CTPT : C6H12O6 CTCT :

CH2OH 5 O H H H 4 1 OH H OH 3 2 OH H OH -Glucoz (vng)

CH2OH H 5 O H H 4 OH H C 1 OH 3 2 H OH Glucoz (mch h)

O H

CH2OH 5 O OH H H 4 1 OH H OH 3 2 H H OH -Glucoz (vng)

Phn t c nhiu nhm OH k nhau nn c tnh cht ca poliancol. Trong phn t v -glucoz, nhm OH ti nguyn t C s 1 c gi l nhm OH hemiaxetal c kh nng m vng. Phn t c nhm CHO nn c tnh cht ca anehit. Fructoz CTPT : C6H12O6 CTCT :
6

HOCH2
5

CH2OH OH
3 2

HOCH2 CH2OH [CHOH]3 CO CH2OH

5

OH OH 2

H
4

H
4

H OH Gc -fructoz

OH Mch h

3 CH2OH H 1 OH Gc -fructoz

Phn t c nhiu nhm OH k nhau nn c tnh cht ca poliancol Trong phn t v -fructoz, nhm OH ti nguyn t C s 2 c gi l nhm OH hemixetal c kh nng m vng.
OH - Fructoz Glucoz Fructoz c tnh kh trong mi trng kim.

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T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Saccaroz
CTPT : C12H22O11 CTCT :
6

CH2OH

H
4

HOCH2
1 2

O HO
4

H
5

OH
3

H
2

H
3

HO

CH2OH
6

OH

OH

Gc -glucoz

Gc -fructoz

Phn t c nhiu nhm OH k nhau nn c tnh cht ca poliancol. Khi thy phn to ra glucoz v fructoz. Khng cn nhm OH hemiaxetal hay hemixetal nn khng th m vng khng c tnh kh. Mantoz CTPT : C12H22O11 CTCT :
6 6

CH2OH

CH2OH O

H
4

H
1 4

H
1

OH
3

H
2

OH
3

H
2

HO

OH OH

OH

Gc -glucoz

Gc -glucoz

Phn t c nhiu nhm OH k nhau nn c tnh cht ca poliancol. Khi thy phn to ra glucoz. Cn 1 nhm OH hemiaxetal nn c th m vng c tnh kh. Tinh bt CTPT : (C6H10O5)n CTCT :

36

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

CH2OH H
4 5

CH2 O H
2

O H
2

H
1

H
4

H
1

H OH
3

H OH
3

OH

Amiloz (khng nhnh) Lin kt -1,4-glicozit

Xenluloz

n Amilopectin (c nhnh) Lin kt -1,4- v -1,6-glicozit

OH

CTPT : (C6H10O5)n hay [C6H7O2(OH)3]n (mi mt xch c 3 nhm OH t do) CTCT :

6

CH2OH H
4 5

O
1

H OH
3

H
2

OH

Xenluoz (khng nhnh) Lin kt -1,4-glicozit

1. Tnh cht ca poli ancol

Glucoz, fructoz, saccaroz, mantoz : tc dng vi Cu(OH)2 to dung dch xanh lam. Xenluloz tan trong dung dch [Cu(NH3)4](OH)2 Glucoz, fructoz, saccaroz, mantoz, xenluloz : cho phn ng vi anhirit ca axit cacboxylic v HNO3 c / H2SO4 c.

2. Tnh cht ca nhm - CH=O

Glucoz, fructoz, mantoz : cho phn ng cng vi H2 (xc tc Ni). Phn ng trng bc : glucoz, fructoz, mantoz.

3. Tham gia phn ng thy phn : isaccarit v polisaccarit.

37

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

K nng Xc nh ng cc nhm chc c trong phn t cc hp cht monosacarit, isaccarit v polisaccarit tnh cht ho hc ca cc hp cht. Gii cc bi tp v hp cht cacbohirat. II. Bi tp p dng A. Trc nghim khch quan 1.
Saccarit l A. hp cht a chc, c cng thc chung l Cn(H2O)m. B. hp cht tp chc, a s c cng thc chung l Cn(H2O)m. C. hp cht cha nhiu nhm hiroxyl v nhm cacboxyl. D. hp cht ch c ngun gc t thc vt.

2.

Glucoz ha tan c Cu(OH)2 v A. glucoz c tnh axit yu B. glucoz c nhm CHO C. glucoz c nhiu nhm OH k nhau D. glucoz c tnh kh. Nhn xt no sau y khng ng ? A. Saccaroz v mantoz u thuc nhm isaccarit. B. Saccaroz v mantoz c cng cng thc phn t. C. Saccaroz v mantoz u to ra hai phn t glucoz khi b thy phn. D. Saccaroz khng c tnh kh, mantoz c tnh kh. Nhn xt no sau y ng ? A. Trong dung dch mantoz c th m vng cn saccaroz th khng. B. Saccaroz v mantoz u c nhm OH hemiaxetal. C. Saccaroz v mantoz u to ra hai phn t glucoz khi b thy phn. D. Saccaroz v mantoz u c phn ng vi dung dch Ag[(NH3)2]OH.

3.

4.

5.

nhn bit cc l mt nhn ng cc cht dung dch : saccaroz, mantoz, etanol, fomalin ta ch cn dng A. Cu(OH)2/OH . C. dung dch Br2.

B. dung dch Ag[(NH3)2]OH. D. vi sa.

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T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

6.

Qu trnh thy phn tinh bt bng enzim khng to ra A. extrin. B. saccaroz. C. mantoz. D. glucoz. Trong cc cht : saccaroz ; tinh bt ; xenluloz ; mantoz ; fructoz ; extrin, s cht c th tham gia phn ng thy phn l A. 3. B. 4. C. 5. D. 6. Pht biu no sau y khng ng ? A. Saccaroz c dng trong cng nghip trng gng. B. Glucoz v saccaroz c sinh ra khi thy phn xenluloz. C. Glucoz v mantoz c sinh ra khi thy phn tinh bt. D. Xenluloz l nguyn liu sn xut ancol etylic. Tinh bt, xenluloz, saccaroz, mantoz u c kh nng tham gia A. phn ng vi [Cu(NH3)4](OH)2. B. phn ng kh vi Cu(OH)2 khi un nng. C. phn ng thy phn. D. phn ng vi Cu(OH)2 nhit phng.

7.

8.

9.

10.

Trong cc cht sau : xenluloz, fructoz, fomalin, mantoz, glixerol, tinh bt, c bao nhiu cht c th phn ng vi Cu(OH)2 iu kin thch hp ? A. 2 B. 3 C. 4 D. 5

B. Trc nghim t lun 1.

in du (+) vo c xy ra phn ng v du () vo khng xy ra phn ng. Glucoz Fructoz Saccaroz Mantoz Tinh Xenluloz bt

[Ag(NH3)2]OH CH3OH/HCl Cu(OH)2 Cu(OH)2, to (CH3CO)2O HNO3/H2SO4

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T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Nc Br2 H2O/ H
+

2. 3. 4. 5.

Vit cc phng trnh ho hc thc hin dy chuyn ho sau : Saccaroz X ancol etylic Y Z ancol etylic Da vo cu to hy gii thch ti sao mantoz cho phn ng trng bc. T xenluloz v cc cht v c cn thit, hy vit cc phng trnh ho hc iu ch xenluloz trinitrat, xenluloz iaxetat. Phn bit cc dung dch sau ng trong cc l mt nhn : a) mantoz, fructoz, saccaroz. b) glucoz, saccaroz, h tinh bt, glixerol un nng dung dch cha 3,42 gam saccaroz vi dung dch H2SO4 long thu c dung dch X. Kim ho dung dch X bng dung dch NaOH ri cho phn ng hon ton vi Cu(OH)2 d thu c 1,44 gam kt ta gch v dung dch Y. Axit ho dung dch Y bng dung dch H2SO4 long ri un nng cho n ht saccaroz th em trung ha bng lng d dung dch NaOH long ta c dung dch Z. Tnh khi lng Ag sinh ra khi cho dung dch Z phn ng vi lng d dung dch AgNO3 trong NH3. Cho xenluloz phn ng vi anhirit axetic thu c 6,6 gam CH3COOH v 11,1 gam hn hp X gm xenluloz triaxetat v xenluloz iaxetat. Tnh phn trm khi lng ca xenluloz triaxetat trong hn hp X. Thy phn hon ton 2,54 gam hn hp X gm saccaroz v mantoz thu c hn hp Y. Bit rng hn hp Y lm mt mu va 100ml nc brom 0,15M. Tnh khi lng Ag to ra nu em 2,54 gam hn hp X cho phn ng lng d AgNO3 trong NH3.

6.

7.

8.

III. Hng dn gii p n A. Trc nghim khch quan

Cu p n 1 B 2 C 3 C 4 B 5 A 6 B 7 C 8 B 9 C 10 C

B. Trc nghim t lun

40

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

1.
Glucoz
[Ag(NH3)2]OH CH3OH/HCl Cu(OH)2 Cu(OH)2, t
o

Fructoz + + + + + +

Saccaroz Mantoz + + + + + + + + + + + +

+ + + + + + +

Tinh bt + + +

Xenluloz + + +

(CH3CO)2O HNO3/H2SO4 Nc Br2 H2O/ H

+

2.

Cc phng trnh ho hc thc hin dy chuyn ho : C12H22O11 + H2O C6H12O6 + Glucoz (X) C6H12O6 2C2H5OH + 2CO2 C2H5OH + CuO CH3CH=O + Cu + H2O (Y)
to
enzim

H+ , t o

C6H12O6 Fructoz

2CH3CH=O + O2 2CH3COOH (Z)

4 CH3COOH C2H5OH

Mn 2 + , t o

LiAlH

3.

Mt trong hai gc glucoz ca mantoz cn nhm OH hemiaxetal nn c th m vng to ra nhm CHO, v vy mantoz cho phn ng trng bc.

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T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

CH2OH H
4 5

CH2OH O
2

H
1

H
4

O
2

H OH
3

HO

H OH
3

H
1

OH

hemiaxetan

OH
6

OH
6

CH2OH H
4 5

CH2OH O
2

H
1

H
4

OH
H OH
2

O C H

H OH
3

HO

OH

OH

4.

T xenluloz v cc cht v c cn thit, hy vit cc phng trnh ho hc iu ch xenluloz trinitrat, xenluloz iaxetat. + iu ch xenluloz trinitrat : [C6H7O2(OH)3]n + 3nHNO3 c [C6H7O2(NO3)3]n + 3nH2O + iu ch xenluloz iaxetat : (C6H10O5)n + nH2O nC6H12O6
H+ , to
enzim

to

C6H12O6 2C2H5OH + 2CO2

C2H5OH + O2 CH3COOH + H2O
2 5 2CH3COOH (CH3CO)2O + H2O

enzim

PO

[C6H7O2(OH)3]n + 2n(CH3CO)2O [C6H7O2(OOCCH3)2OH]n + 2nCH3COOH

5.
a) Phn bit : mantoz, fructoz, saccaroz. Dng nc brom nhn bit dung dch mantoz. Dng dung dch AgNO3 trong NH3 nhn bit fructoz. Cn li l saccaroz. b) Phn bit : glucoz, saccaroz, h tinh bt, glixerol - Dng dung dch I2 nhn bit h tinh bt. - Dng nc brom nhn bit dung dch glucoz: mt mu nc brom.

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T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

- Thm vi git dung dch H2SO4 vo 2 mu th cn li ri un nh khong 3 pht, sau trung ha bng dung dch NaOH ri nhn bit sn phm thy phn ca saccaroz bng dung dch AgNO3 trong NH3 do to Ag kt ta.

6.
Phn ng thy phn : C12H22O11 + H2O C6H12O6 + C6H12O6 Glucoz Fructoz Trong mi trng kim, fructoz chuyn ho thnh glucoz.
H+ , t o

(1)

C5H11O5CHO + 2Cu(OH)2 + NaOH Cu2O + C5H11O5COONa + 3H2O (2) 1, 44 Theo (2) : s mol glucoz = s mol Cu2O = = 0, 01 (mol) 144 y cng chnh l tng s mol glucoz v fructoz trong dung dch X to ra (1). Theo (1) : 1 S mol saccaroz thy phn = s mol (glucoz v fructoz) = 0,005 mol 2 6,84 0, 005.342 S mol saccaroz cn li trong Y = = 0,015 (mol) 342 Theo (1) : S mol (glucoz v fructoz) trong Z = 2 s mol saccaroz trong Y = 2.0,015 = 0,03 (mol) Trong mi trng kim, fructoz chuyn ho thnh glucoz: C5H11O5CHO + 2[Ag(NH3)2]OH 2Ag + C5H11O5COONH4 + 3NH3 + H2O (3)

s mol Ag = 2 s mol (glucoz v fructoz) = 2.0,03 = 0,06 (mol)

Khi lng Ag thu c = 0,06.108 = 6,48 (gam).

7.
[C6H7O2(OH)3]n 2nCH3COOH 1 x + 2n(CH3CO)2O

[C6H7O2(OOCCH3)2OH]n 1 x 2n 2nx

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T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

[C6H7O2(OH)3]n+ 3n (CH3CO)2O [C6H7O2(OOCCH3)3 ]n + 3nCH3COOH 1 1 3n y y 3ny Ta c : Khi lng CH3COOH = 6,6 gam 2nx +3ny = 0,11 mol (1) Khi lng xenluloz iaxetat v xenluloz triaxetat = 11,1 gam 246nx + 288ny = 11,1 gam (2) Gii h phng trnh (1) v (2 ) ta c : nx = 0,01 v ny = 0,03 Khi lng xenluloz triaxetat = 8,64 gam 8,64 Vy %mxenluloz triaxetat trong hn hp X = 100 = 77,84 %. 11,1

8.
S mol Br2 = 0,1.0,15 = 0,015 mol C12H22O11 (Sac) + H2O C6H12O6 (Glu) + C6H12O6 (Fruc) x x x C12H22O11 (Man) + H2O 2C6H12O6 (Glu) y 2y Ch c glucoz phn ng vi Br2 : CH2OH[CHOH]4CHO + Br2 + H2O CH2OH[CHOH]4COOH + 2HBr x + 2y x + 2y x + 2y = 0,015 mol (1) Theo : 254(x + y) = 2,54 gam (2) Gii h phng trnh (1) v (2) ta c : x = y = 0,005 mol Mt phn t mantoz cha 1 nhm CHO nn : 1 mol mantoz + phn ng vi 2 mol [Ag(NH3)2]OH 2 mol Ag 0,005 mol mantoz khi phn ng to ra 0,01 mol Ag Khi lng Ag sinh ra l : 0,01.108 = 1,08 (gam)

44

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Chng 3. AMIN - AMINO AXIT - PROTEIN

I. Kin thc trng tm
Nm vng cng thc cu to ca amin, amino axit, protein tnh cht c bn cc cht. Amin R"

NH2

NH

R'

R'
+

Amin bc I

Amin bc II

Amin bc III

Nguyn t N cn cp electron t do nn amin c kh nng nhn H c tnh baz (tng t NH3). Nhm R y electron (nhm ankyl) lm tng lc baz, nhm R ht electron (nhm phenyl) lm gim lc baz. Amino axit (H2N)aR(COOH)b c bit -amino axit : R CH COOH (nhm NH2 gn vo C s 2) | NH 2 Phn t c ng thi 2 nhm NH2 v COOH l hp cht lng tnh. Protein ... NH CH CO NH CH CO ... R R Phn t c nhiu nhm peptit CONH tham gia phn ng thy phn.
1 2

1. Tnh cht Amin

Tnh baz : phn ng vi H . Cc amin bc I phn ng vi axit HNO2 ancol v kh N2. Ring amin thm + Phn ng vi HNO2 ( 0 5 C) mui iazoni.
o o +

45

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

+ Do nh hng ca nhm NH2 i vi vng benzen tc dng vi dung dch Br2 kt ta trng. + Do nh hng ca vng benzen i vi nhm NH2 lm gim tnh baz rt t tan trong nc v gn nh khng phn ng vi nc Phn ng vi ankyl halogenua amin bc cao hn. Amino axit Tnh lng tnh : + To mui ni (ion lng cc) nn d tan trong nc. + Phn ng vi axit v baz. Phn ng este ho (do c nhm COOH). Phn ng vi HNO2 (do c nhm NH2). Phn ng trng ngng poliamit sn xut t tng hp. Ring -amino axit c phn ng trng ngng polipeptit protein. Protein Phn ng thy phn cc -amino axit. Phn ng vi Cu(OH)2 sn phm mu tm. Phn ng vi HNO3 kt ta vng. Ch : + Lin kt peptit ch c hnh thnh gia cc -amino axit. + Nu phn t peptit cha n gc -amino axit khc nhau th s c n! ng phn loi peptit. K nng So snh tnh baz ca cc amin. Da vo cu to gii thch tnh cht vt l v ho hc ca amin v amino axit. Vit phng trnh ho hc ca phn ng trng hp, trng ngng iu ch cc loi t. Gii cc bi tp v amin, amino axit, protein.

II. Bi tp p dng A. Trc nghim khch quan 1.

Dy cc cht c xp theo c sp xp theo th t tng dn mnh ca tnh baz l A. (C6H5)2NH < C6H5NH2 < (C2H5)2NH < C2H5NH2 < NH3

46

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

B. C2H5NH2 < (C2H5)2NH < C6H5NH2 < NH3 <(C6H5)2NH C. C2H5NH2 < (C2H5)2NH < C6H5NH2 < NH3 <(C6H5)2NH D. (C6H5)2NH < C6H5NH2 < NH3 < C2H5NH2 < (C2H5)2NH

2.

3.

Thc hin phn ng trng ngng 2 amino axit : glyxin v alanin thu c ti a s ipeptit l A. 1. B. 2. C. 3. D. 4. Cho nc brom vo dung dch anilin, thu c 16,5 gam kt ta 2,4,6-tribromanilin. Khi lng anilin tham gia phn ng l A. 30 gam. B. 34 gam. C. 36 gam. D. 32 gam. Ho cht c dng phn bit ba dung dch : H2NCH2COOH, HOOCCH2CH(NH2)COOH, H2NCH2CH2CH(NH2)COOH l A. phenolphtalein. B. giy qu tm. C. AgNO3 dung dch trong NH3. D. dung dch HCl. Dy gm cc cht tan nhiu trong nc to thnh dung dch trong sut l A. imetylamin, anilin, glyxin. B. imetylamin, glyxin, anbumin. C. etylamin, 2,4,6-tribromanilin, alanin. D. etylamin, alanin, axit glutamic. A l mt amino axit c phn t khi l 147. Bit 1 mol A tc dng va vi 1 mol HCl v 0,5 mol A tc dng va vi 1 mol NaOH. Cng thc phn t ca A l A. C5H9NO4. C. C5H25NO3. B. C4H7N2O4. D. C8H5NO2.

4.

5.

6.

7.

Nhn nh no sau y khng ng ? A. Cc amin u c tnh baz do nguyn t nit c i electron cha tham gia lin kt. B. Cc amino axit u c cn bng gia dng phn t vi dng ion lng cc. C. Thy phn n cng cc protein u thu c cc -amino axit. D. Cc amino axit u tham gia phn ng trng ngng to thnh polipeptit

47

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

8.

Cc cht trong dy no sau y u tc dng vi dung dch HCl ? A. ClH3NCH(NH2)COOH, H2NCH2COOH HOOCCH2CH2CH(NH2)COOH,

B. ClH3NCH2COOH, ClH3NCH2COONa, H2NCH2COOH C. HOOCCH2CH2CH2COOH, ClH3NCH2COONa, CH3COONH4 D. HOOCCH2CH2CH(NH2)COOH, ClH3NCH2COOH, CH3COONH4

9.

S hp cht hu c c cng cng thc phn t C3H7O2N, u tc dng c vi dung dch HCl v dung dch NaOH l A. 1. B. 2. C. 3. D. 4. Cho 0,1 mol X c cng thc H2NCxHyCOOH phn ng ht vi HCl to 11,15 gam mui. X l A. axit aminoaxetic B. axit 2-aminopropanoic C. axit 2-amino-3-phenylpropanoic D. axit 2-amino-3-metylbutanoic

10.

B. Trc nghim t lun 1. 2.

Vit cng thc cu to v gi tn cc ng phn, ch r bc ca cc amin c cng thc phn t C4H11N. a) Trong phng th nghim nn chn ho cht no ra sch l cha anilin ? b) kh mi tanh ca c dnh trn cc vt dng trong nh bp ta nn dng cht g ? c) V sao khng nn git o qun c cht liu l t tm hay len bng x phng c kim cao ? Vit cc phng trnh ho hc xy ra (nu c) khi cho : a) Metylamin phn ng vi : H2O, H2SO4, CH3I, HNO2, dung dch CuSO4. b) Anilin phn ng vi : H2O, dung dch Br2, HCl, HNO2/ HCl (0 5 C). Cho hp cht X c cng thc : NH2 CH2 CO NH CH CO NH CH COOH
CH3 CH CH3 CH3
o

3.

4.

48

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

5.

a) Hp cht X thuc loi hp cht hu c g ? c to thnh t cc amino axit no ? Hy gi tn y v tn vit gn ca X. b) Hp cht X c bao nhiu ng phn cu to loi peptit ? Cho bit tn thu gn ca cc ng phn . a) Ch dng nc v dung dch HCl, hy phn bit 4 l mt nhn cha 4 cht lng : ancol etylic, phenol, anilin, benzen. b) Phn bit 5 l mt nhn cha 5 cht dung dch : NH2CH2COOH, C2H5NH2, CH3COOH, HOOC(NH2)CHCOOH, NH3.

6.

7.

8.

Khi cho amin X n chc vo dung dch cha hn hp NaNO2 v HCl thy c kh thot ra. Mt khc khi cho X tc dng vi dung dch FeCl2 d thu c khi lng kt ta ng bng khi lng X tham gia phn ng. a) Vit cc phng trnh ho hc. b) Xc nh cng thc cu to ca X. Cho 0,1 mol -amino axit phn ng va vi 100ml dung dch NaOH 1M, sau phn ng thu c 11,1 gam mui khan. Xc nh cng thc cu to ca -amino axit . t chy hon ton 17,8 gam hp cht amino axit c ly t thin nhin ngi ta thu c 13,44 L kh CO2, 12,6 gam nc v 1,12 L N2. Mt khc, khi cho 0,1 mol A phn ng ht vi hn hp NaNO2 v HCl, ngi ta thu c 2,24 L kh N2. Cc cht kh u o iu kin tiu chun. a) Xc nh cng thc cu to thu gn ca A. b) A c tan c trong nc khng ? V sao ?

III. Hng dn gii p n A. Trc nghim khch quan

Cu p n 1 D 2 D 3 B 4 B 5 D 6 A 7 D 8 A 9 D 10 A

B. Trc nghim t lun 1.

Cch vit ng phn amin : 4 2 + 2 11 + 1 = 0 mch C no v h C4H11N + v = 2

49

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Ch c 2 ng phn mch C l : C C C C v C C C . | C Gn nhm NH2 vo cc nguyn t C ca cc mch c cc ng phn amin bc I : C C C C NH2 C C C C

butylamin

NH2 but-2-ylamin (hay sec-butylamin) C

NH2

NH2

C 2-metylprop-1-ylamin (hay isobutylamin)

:
C C C NH C C C

C 2-metylprop-2-ylamin (hay tert-butylamin)

Chn nhm NH vo gia mch C c cc ng phn amin bc II

NH C C C C NH C

metylpropylamin

ietylamin

C isopropylmetylamin

- Gn 3 nhm ankyl vo nguyn t N c amin bc III : C

C C N C etylimetylamin

2.

3.

a) Trong phng th nghim nn dng dung dch axit (nh dung dch HCl long) ra sch l cha anilin v anilin l mt baz, cc axit phn ng vi anilin to ra mui tan. b) kh mi tanh ca c dnh trn cc vt dng trong nh bp ta nn dng gim hay chanh v mi tanh ca c l do hn hp nhiu amin to ra. Cc axit c trong chanh hay gim phn ng vi cc amin ny lm mt mi tanh. c) T tm hay len c to thnh t cc polipeptit. Khi git o qun bng x phng c kim cao th cc polipeptit s b thy phn trong mi trng kim nn lm hng qun o . Cc phng trnh ho hc :

50

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

a)

CH3NH2 + H2O
CH3NH2 + CH3I

CH3NH3

+ +

+ OH

2CH3NH2 + H2SO4
CH3NH2 + HNO2 b) C6H5NH2 + HCl C6H5NH2 + 3Br2

2CH3NH3 + SO2 4
(CH3)2NH + HI CH3OH + N2 + H2O

+ 2CH3NH2 + 2H2O + CuSO4 Cu(OH)2 + 2CH3 NH3 + SO2 4 + C 6 H5 NH3 + Cl

+

Br3C6H2NH2 + 3HBr

4.

5.

C6H5NH2 + HNO2 + HCl C6H5N2 Cl + 2H2O a) Hp cht X l mt tripeptit. c to thnh t 3 -amino axit : glyxin, valin v alanin. Tn y ca X l : Glyxylvalinalanin Tn vit gn ca X l : Gly-Val-Ala b) X c to thnh t 3 -amino axit nn X c s ng phn loi peptit l : 3! = 1 2 3 = 6 ng phn. Tn thu gn ca 6 ng phn l : Gly-Val-Ala ; Gly-Ala-Val ; Val-Gly-Ala ; Val-Ala-Gly ; Ala-Gly-Val ; Ala-Val-Gly. a) Phn bit 4 l mt nhn cha 4 cht lng : ancol etylic, phenol, anilin, benzen. Trch cc mu th ri cho cc mu th vo nc, ch c ancol etylic tan. un nh 3 mu th cn li, phenol tan trong nc nng to thnh dung dch trong sut. Sau cho 2 mu th cn li vo dung dch HCl, ch c anilin tan : C6H5NH2 + HCl C6H5NH3Cl Cn benzen khng tan. b) Phn bit 5 l mt nhn cha 5 dung dch : NH2CH2COOH, C2H5NH2, CH3COOH, HOOC(NH2)CHCOOH, C6H5NH2. Cho qu tm vo cc mu th : + Mu th lm qu tm ho xanh l C2H5NH2 . + 2 mu th khng lm i mu qu tm l NH2CH2COOH, C6H5NH2.

51

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Cho dung dch Br2 vo 2 mu th ny, mu th to kt ta trng l C6H5NH2, cn li l NH2CH2COOH. C6H5NH2 + 3Br2 Br3C6H2NH2 + 3HBr + 2 mu th lm mu qu tm ho l : CH3COOH v HOOC(NH2)CHCOOH. Cho hn hp NaNO2 v CH3COOH ( to ra HNO2) vo 2 mu th ny, mu th c kh bay ra l HOOC(NH2)CHCOOH, cn li l CH3COOH.

6.

HOOC(NH2)CHCOOH + HNO2 HOOC(OH)CHCOOH + N2 + H2O a) Cc phng trnh ho hc : HCl + NaNO2 HNO2 + NaCl X (amin n chc) phn ng vi HNO2 c kh bay ra

X l amin bc I c cng thc CxHyNH2

CxHyNH2 + HNO2 CxHyOH + N2 + H2O 2CxHyNH2 + 2H2O + FeCl 2 Fe(OH)2 + CxHyNH3Cl b) Xc nh cng thc cu to : Gi a l s gam X tham gia phn ng 2CxHyNH2 a + 2H2O + FeCl 2 Fe(OH)2 + CxHyNH3Cl 90 a 2(12x + y + 16)

12x + y + 16 = 45 12x + y = 29 y = 29 12x cp nghim hp l l x = 1 v y = 5 7. cng thc cu to ca X l CH2CH2NH2. S mol NaOH = 0,1.1 = 0,1 (mol)
(H2N)aCxHy(COOH)b + bNaOH (H2N)aCxHy(COONa)b + bH2O 1 0,1 b 0,1 1 0,1

b = 1 Cng thc phn t c dng (H2N)aCxHy(COOH) Khi lng mui = (16a + 12x + y + 67).0,1 = 11,1 gam 12x + y + 16a = 44 12x + y = 44 16a a = 1 12x + y = 28 x = 2 v y = 4

52

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

CTCT : CH3CH(NH2)COOH. a = 2 12x + y = 12 x = 1 v y = 0 CTCT : (NH2)2CCOOH : loi v khng ph hp vi ho tr cacbon.

8.
a) n C = n CO2 = 13,44 = 0,6 (mol) mC = 0,6.12 = 7,2 (gam) 22,4

mH =

12,6 2 =1,4 (gam) 18 2, 24 n N2 = = 0,1 (mol) m N = 28.0,1 = 2,8 (gam) 22,4

mO = 17,8 (7,2 + 1,4 + 2,8) = 6,4 (gam) t CTPT ca A c dng : CxHyOzNt m m m 7, 2 6, 4 2, 8 =3:7:2:1 x : y : z : t = C : mH : O : N = : 1, 4 : : 12 16 14 12 16 14

CTPT ca A c dng : (C3H7O2N)n Theo : 0,1 mol A phn ng vi HNO2 (NaNO2 + HCl) 0,1 mol N2

phn t A cha 1 nhm NH2 phn t A ch c 1 nguyn t N. CTPT ca A l C3H7O2N. V amino axit A c ly t thin nhin A l -amino axit CTCT ca A : NH2CH(CH3)COOH
b) A tn ti dng ion lng cc : NH3CH(CH3)COO trong nc l dung mi phn cc.
+

nn d tan

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T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Chng 4. POLIME
I. Kin thc trng tm a) Hiu cc khi nim Monome, polime, mt xch, h s polime ho
mt xch

n CH2

CH2

xt, t , p

CH2

CH2 n

h s polime ho

polime

b) Bit cc vt liu polime : Cht do, vt liu compozit, t, cao su. c) Phn loi ng cc polime : Theo ngun gc : polime thin nhin, tng hp v nhn to. Theo cch tng hp : polime trng hp v trng ngng. d) Nm vng tnh cht : Tnh cht vt l : + Hu ht l cht rn, khng c nhit nng chy nht nh. + Mt s c tnh do, mt s c tnh n hi, mt s c tnh dai... Tnh cht ho hc : + Phn ng gi nguyn mch polime : Phn ng cng : khi mch chnh hay nhm th c lin kt bi. Phn ng th : th vo mch chnh hay th cc nhm chc. + Phn ng ct mch polime : Cc polime c to thnh do phn ng trng hp thng b nhit phn : polistiren, cao su... Cc polime c to thnh do phn ng trng ngng thng b thy phn : cc polime c nhm CONH ; CO ...
+ Phn ng khu mch polime : to cc cu ni SS hay CH2 hnh thnh mng li. K nng Vit c phn ng trng hp, ng trng hp v trng ngng. T monome xc nh c polime v ngc li Vit c cc s phn ng iu ch :

54

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

+ 5 loi cao su : cao su buna ; cao su isopren ; cao su cloropren ; cao su buna-N ; cao su buna-S. T nguyn liu u l kh thin nhin v sn phm du m. + 7 loi t : nilon-6 ; nilon-7 ; nilon-6,6 ; lapsan, olon (nitrin), visco, xenluloz axetat. + Mt s polime thng gp : PE, PVC, PVA, PMMA, PS... t nguyn liu u l kh thin nhin v sn phm du m Gii cc bi tp nh lng v polime, tnh hiu sut.

II. Bi tp p dng A. Trc nghim khch quan 1.

C bao nhiu vt liu polime trong cc vt liu sau : gm, g, nha, la, len, compozit, protein. A. 4. B. 5. C. 6. D. 7. Dy chuyn ho no sau y khng ng ? A. C2H2 C4H4 C4H6 Cao su buna B. C2H2 CH3CHO C2H5OH C4H6 Cao su buna C. C2H2 C2H3OH C2H5OH C4H6 Cao su buna D. C2H2 C2H6 C2H5Cl C2H5OH C4H6 Cao su buna

2.

3.

4.

T cht u l etilen v cc nguyn liu v c khc c th iu ch PVC vi s phong trnh ho hc ti thiu l A. 3. B. 4. C. 5. D. 6. Nhm gm cc loi t c ngun gc xenluloz l : A. t tm ; vi si ; len. B. len ; t nilon-6 ; t axetat. C. vi si ; t visco. D. t tm ; vi si. Nhn xt no sau y ng ? A. Cc loi si vi, si len u l t thin nhin. B. T nilon-6 l t nhn to. C. T visco l t tng hp. D. T xenluloz axetat l t ho hc.

5.

55

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

6.

Pht biu no sau y ng ? A. Cao su buna l sn phm ng trng hp ca buta-1,3-ien v natri. B. Cao su thin nhin l sn phm trng hp ca cloropren. C. Cao su buna-S l mt loi copolime. D. Cao su buna-N l sn phm ca phn ng trng ngng. Phng php iu ch polime no sau y ng ? A. Trng ngng caprolactam to ra t nilon-6. B. ng trng hp axit terephtalic v etylen glicol c poli(etylen terephtalat). C. ng trng hp buta-1,3-ien v vinyl xianua c cao su buna-N. D. Trng hp ancol vinylic c poli(vinyl ancol). Dy chuyn ho no sau y khng ng ? A. Tinh bt extrin Mantoz Glucoz Glicogen B. Tinh bt Saccaroz Glucoz CO2 Glucoz C. Tinh bt extrin Mantz Glucoz CO2 D. Tinh bt extrin Saccaroz Glucoz Cng thc no sau y khng phi ca cao su ?

7.

8.

9.

A.

B.

n
Cl
C. D.

CN

10.

Pht biu no sau y khng ng ? A. T nilon-6,6 l polime c hnh thnh do cc lin kt peptit. B. T lapsan c tng hp t axit terephtalic v etylen glicol. C. T nitron thuc loi t vinylic. D. Len, bng l cc loi polime thin nhin.

56

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

B. Trc nghim t lun 1.

a) Vit cc phng trnh ho hc iu ch cc polime bng cc phng php : trng hp, ng trng hp, trng ngng. b) Vit phng trnh ho hc minh ha cho s chuyn ho t polime ny sang polime sang polime khc. c) Cho polime sau : ( NH [CH 2 ]5 CO )n Polime trn c iu ch bng nhng phng php no ? Vit phng trnh ho hc ca phn ng iu ch polime . Vit cc phng trnh ho hc iu ch cc polime sau : a) PVA, PVC, thy tinh hu c plexiglas (PMMA) t butan v cc cht v c cn thit. b) Cao su buna-S v cao su cloropren t cc sn phm ca du m l hexan, butan, etan. c) Poli(etylen-terephtalat) cn gi l t lapsan t cc nguyn liu u l p-xilen v etilen. d) Keo dn ure-fomanehit t cc kh CO2, NH3 v CH4. iu ch cao su buna-N ngi ta xut pht t nguyn liu hu c ban u l kh butan v metan. a) Vit cc phng trnh ho hc xy ra. b) Tnh th tch kh butan v kh metan cn dng ( ktc) iu ch 1 tn cao su buna-N. Bit hiu sut chung ca c qu trnh l 45%. Trc kia ngi ta iu ch cao su buna theo phng php ca Le-be-ep t nguyn liu u l tinh bt. Vit cc phng trnh ho hc v tnh khi lng bt m cha 90% tinh bt cn sn xut 1 tn cao su. Bit rng hiu sut trung bnh ca mi giai on l 60%.

2.

3.

4.

III. Hng dn gii p n A. Trc nghim khch quan

Cu p n 1 C 2 C 3 A 4 C 5 D 6 C 7 C 8 A 9 B 10 A

57

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

B. Trc nghim t lun 1.

a) + Phng php trng hp :

n CH CH3

CH2

xt,t o ,p

CH CH3

CH2
n

+ Phng php trng ngng : nNH 2 [CH 2 ]6 COOH ( NH [CH 2 ]6 CO )n + H 2 O + Phng php ng trng hp :
xt,t o ,p

n CH2

CH CH CH2 + n CH CH2

xt,t o ,p

CH2

CH CH CH2 CH CH2
n

b)

CH2

CH OOCCH3 n

+ nNaOH

CH2

CH OH n

+ nCH3COONa

c) + iu ch bng phng php trng hp : CH2 CH2 CO H2O nH2C CH2 CH2 NH
+ iu ch bng phng php trng ngng :
xt,t o

NH

[CH2]5

CO

nNH 2 [CH 2 ]5 COOH ( NH [CH 2 ]5 CO ) n + H 2 O

2.

a) + iu ch PVA : CH3CH2CH2CH3 CH3CH=CH2 + CH4

xt,t o 1500o C

2CH4 CH CH + 3H2

58

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Hg ,H ,t CH CH + H2O CH3CHO

2+

+ o

2CH3CHO + O2 2CH3COOH CH CH + CH3COOH CH2=CHOOCCH3 n CH2 + iu ch PVC : CH3CH2CH2CH3 CH3CH3 + CH2 = CH2 CH2 = CH2 + Cl2 CH2Cl CH2Cl CH2ClCH2Cl CH2 = CH Cl + HCl
500o C xt,t o xt,t o ,p
xt,t o

Mn 2+ , t o

CH OOCCH3

CH 2 CH OOCCH3 n

n CH 2

CH

xt,t o ,p

CH2

CH Cl
n

Cl + iu ch thy tinh hu c :
xt,t o xt,t o

CH3CH2CH2CH3 CH3CH=CH2 + CH4 CH4 + O2 CH3OH CH3CH=CH2 + H2O CH3CHOHCH3 CH3CHOHCH3 + CuO CH3COCH3 + Cu + H2O CN CH3 C O CN CH3 C
3 CH3 CH3

H + ,t o to

CH3 + HCN CH3

CH3

OH COOH
H O + ,t o

C OH

CH3

OH COOH

CH3

C OH

2 4 CH3 CH2 o

H SO c 180 C

C CH3

COOH + H2O

59

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

CH2

C CH3

2 4 COOH + CH3OH CH2 to

H SO c

COO

CH3 + H2O

CH2

C CH3

COO

CH3

xt,t o ,p

CH3 COOCH3

CH2

C CH3
n

b) + iu ch cao su buna-S : CH3CH2CH2CH3 CH2=CHCH=CH2 + 2H2

xt,t o

CH3CH2CH2CH2CH2CH3
xt,t o

rifominh

+ 4H2

CH3CH3 CH2=CH2 + H2
+ CH 2=CH2
H+

CH2CH3

CH2CH3

xt, to

CH=CH2 + H2

xt, to, p nCH2=CH-CH=CH2 + nCH=CH2

CH2-CH=CH-CH2

CH-CH2

n
+ iu ch cao su cloropren : CH3CH2CH2CH3 CH3CH=CH2 + CH4
xt,t o 1500o C

2CH4 CH CH + 3H2
xt,t CH CH CH2=CHCCH
o

60

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

CH 2 = CH C CH + HCl CH 2 = CH C = CH 2 | Cl
n CH2=CH C=CH2 Cl
xt, p, to

CH2 CH

C Cl

CH2 n

c) iu ch t lapsan :
3CH2=CH2 + 2KMnO4 + 4H2O CH3 CH3
+ KMnO4 , t
o

3CH2OH-CH2OH + 2KOH + 2MnO2 KOOC COOK

KOOC

COOK + H2SO4

HOOC

COOH + K2SO4

nHOOC

tO, xt COOH + n HO CH2 CH2 OH OC

nH2O

CO O CH2 CH2 O

d) Keo dn ure-fomanehit CO2 + 2NH3 (NH 2 )2 CO + H 2 O CH 4 + O2 HCHO + H 2 O (NH 2 )2 CO NH 2 CO NH CH 2 OH ( NH CO NH CH 2 ) + nH 2 O

H + ,t o H + ,t o xt,t o 180o C, 200 atm

3.

a) Cc phng trnh ho hc : CH3CH 2 CH 2 CH3 CH 2 = CH CH = CH 2 + 2H 2

2CH4 CH CH + 3H2
1500o C xt,t o

CH CH + HCN CH 2 = CH CN

xt,t o

61

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

nCH 2 = CH CH = CH 2 + nCH 2 = CH CN ( CH 2 CH = CH CH 2 CH 2 CH )n | CN b) Th tch kh butan v kh metan cn dng : T 4 phng trnh ho hc trn ta c s : n mol C4H10 v 2n mol CH4 1 mol cao su buna-N 58n gam 107n gam x? 10 gam 106 58n 543056 (gam) 107n
6

xt,t o ,p

Khi lng C4H10 theo l thuyt cn dng = x =

Th tch C4H10 theo l thuyt = 209345,8 L

Th tch C4H10 theo thc t : 100 3 = 209345,8 = 465212, 9 L 465,213 m 45 Theo s trn : s mol CH4 = 2 s mol C4H10

Th tch CH4 = 2 th tch C4H10 = 930,426 m3. 4. Cc phng trnh ho hc :

xt, t (C6H10O5)n + nH2O nC6H12O6
o

C6H12O6 2C2H5OH + 2CO2

2 3 2C2H5OH CH2=CHCH=CH2 + 2H2O + H2 o

enzim

Al O ,MgO 450 C

xCH2=CHCH=CH2 ( CH 2 CH = CH CH 2 )x T phn ng trng hp : khi lng C4H6 = khi lng cao su buna = 1 tn = 106 gam T 4 phn ng trn ta c : (C6H10O5)n nC6H12O6 2nC2H5OH nC4H6 Cao su buna 162n gam 54n gam ? 106 gam

xt,t o ,p

62

T V B H TR NG TM KI N TH C V GI I BI T P HA H C 12

D&3H

Khi lng tinh bt cn dng theo l thuyt =

Khi lng tinh bt cn dng theo thc t =

106.54n (gam) 162n

106.54n 100 100 100 100 100 2,86.106 gam = 2,86 tn 162n 90 60 60 60 60

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