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Bi tp Axit caboxylic GVHD: Nguyn Th M !h"#ng

BI TP CHNG XII: AXIT CACBOXYLIC V DN XUT
BI 1: AXIT CACBOXYLIC
I. DANH PHP
Bi 1: $%c t&n c'c h#p ch(t )au th*o +anh ph'p ,-!A.:
a/ .H
0
.H
1
.2.H
1
.22H b/ .H
0
.H
1
.2.H
1
.22H
c/ .H
0
.H3.H
0
4.H3.H
0
4.H
1
.22H +/ H22. 5 H
1
. 5 .2 5 .H
1
5 .22H
*/ .H
0
3.H
1
4
1
.H3.2.H
0
4.H
1
.H
1
.22H 6/ .H
0
.H2H.H3.H
1
.H
1
2H4.H
1
.22H
g/ .H
0
3.H
1
4
7
.H8.H3.H
1
4
7
5 .22H h/ H2 5 .3.H
1
.22H4
1
5 .22H
i/ .H
0
.H2H.H3.
1
H
9
2H4.H
1
.22H :
;/ l/
Bi 2: $%c t&n c'c h#p ch(t )au th*o t&n th"<ng = th*o +anh ph'p ,-!A.:
a. b/
c/ +/
*/ 6/
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CH
2
COOH
H
2
NCH
2
CHCH
2
COOH
OCH
2
COOH
Cl
Cl
Cl
OOCCH
3
COOH
CH
2
COOH
Cl
Cl
Cl
C CHCOOH
CH
3
COOH
OH
COOH
OH
NHCOC
6
H
5
C
12
H
24
COOH
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Bi tp Axit caboxylic GVHD: Nguyn Th M !h"#ng
Bi 3: H?y =i@t cAng thBc c(u tCo cho c'c axit cacboxylic cD t&n g%i )au EFy:
a/ Axit i)o=al*ric b/ Axit ph*nylax*tic
c/ Axit aEipic +/ Axit p 5 toluic
*/ Axit phtalic 6/ Axit i)ophtalic
g/ Axit t*r*phtalic h/ Axit Gal*ic
i/ ,)obutyronitril :/ Axit p 5 hi+roxib*nHoic
;/ Axit triG*tylax*tic
II. PHNG T!NH PH"N #NG
Bi 1: Vi@t ph"Ing trJnh phKn Bng xKy ra giLa axit ax*tic = c'c h#p ch(t )au:
a/ MgM Na2HM )au ED nung h#p ch(t thu E"#c
b/ .a32H4
1
)au ED nung nDng h#p ch(t thu E"#c/
c/ NH
0
M )au ED nung nDng h#p ch(t thu E"#c /
+/ .a.2
0
N !.l
9
N .
1
H
9
2H cD GOt H
1
>2
P
EOc N .l
1
Q!
Bi 2: .ho bi@t )Kn phRG tCo thnh ;hi cho c'c h#p ch(t )au EFy t'c +Sng =Ti axit propanoic:
a/ >2.l
1
b/ !Br
0
c/ .H
0
5 .H
1
5 .2Br
+/ 3.H
0
4
1
.H2H M H
U
*/ V2HM .H
0
5 .H
1
,
6/ .
W
H
9
5 .H
1
5 NH
1
g/ .
W
H
9
Xi
h/ XiAlH
P
Bi 3: Hon thnh c'c ph"Ing trJnh phKn Bng )au:
a/
Y
W 9 P
t
C H CH CHCOOH KMnO OH

= + +
b/
Y
0 W P 0 1 P
t C
p CH C H COOH HNO H SO + +
c/ Axit butyric U Br
1

do
P

+/ Axit ol*ic U VMn2

P
U 2H
Z

Y
t

e. Axit ol*ic U Br
1
Q ..l
P

f. Axit ol*ic UH.2

1
2H

g/
W 9 1 1
1
H
C H COOH HOCH CH OH
+
+
h/
W P 1
Fe
o HOC H COOH Br +
Bi $: Vi@t ph"Ing trJnh phKn Bng ;hi cho axit b*nHoic t'c +Sng =Ti c'c h#p ch(t )au:
a/ V2H b/ Al
c/ HN2
0 EOc
Q H
1
>2
P EOc
+/ !.l
9
*/ ++ VMn2
P
M nDng 6/ XiAlH
P
g/ .a2 h/ Na
1
.2
0
i/ Dung +ch NH
0
:/ H
1
M x[c t'c NiM 1Y
Y
.M 1atG
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Trang 0
Bi tp Axit caboxylic GVHD: Nguyn Th M !h"#ng
;/ Axit )un6uric b\c ;h\i l/ .H
0
.lM Al.l
0
Bi %: H?y tJG cAng thBc c(u tCo c]a c'c h#p ch(t ^M _M `M T:
a/ Ax*til*n U .H
0
MgBr

.H
P
U ^
b. ^ U .2
1

_
0 1 1
3 4
H
Z C H O
+

c.
1 1 P P
M M
0 P 0
3 4
H O H SO HgSO
Z T C H O
d.
P 1 1
3 4 T KMnO CH COOH +
III. CHU&I PH"N #NG
Bi 1: Hon thnh c'c chuai phKn Bng )au:
a/
1 1
W 9 0
Cl H O KCN
askt HCl
C H CH A B C
b/
1
W 9 1 1
H O KCN
HCl
X C H CH CH CN Y
c/
[ ]
9 1
1
0 1 0
H PCl H O KCN
HCl
CH COCH CH A B C E
+/
( )
[ ]
Y
9 0 1 9 1 9
1 9
M
0
1
H PCl NH t P O C H ONa
Na C H OH
CH CH COOH A B C D E
+

Bi 2: Hon thnh c'c chuai phKn Bng )au
a/
0 P 1
PBr LiAlH CO H Mg H
ete
Aitpan!iti" A B C D E F
+ +

b/
0 1 P
P 1
P
/
0 1 1 0 P 0
1 1
3 4 3 4
3 4
CH MgBr CO HgSO H H
CH H O
KMnO
Aetilen A B C C H O D C H O
CH COOH
+ +

c/
0 1 1
1 1 1 1 P
Y Y
1 P
3 4
W 9
M 17Y
K#an
PBr CH O Mg HCl NaCN
ete
HF H O SOCl H H SO
a$l#oa Ni H SO t C
C H Br A B C D E
F % H & K


Bi 3: Hon thnh c'c )I Eb phKn Bng )au EFy:
a/
0
P
H O C'Cl
NH Cl
HC CH HCN A B
+
+
b/
Y
W 9 1 1
3 4
piperidin t C
C H CHO CH COOH T H +
Bi $: Hon thnh chuai )au:
a.
0 0 0 P 1 1 0 1
CH CHO CH COOH CH COONa CH C H CH CHO ClCH CHO
b. H.CH + CH3MgBr (A) + (B)
0 1 P
P 1 P
1
Q
3 4 3 4 3 4 3 4
H O H O KMnO
HgSO H SO
A CO C D E F
+
+
+
IV. 'I(U CH)
Bi 1: Tc tolu*n* = c'c ch(t =A cI cdn thi@tM =i@t )I Eb teng h#p c'c ch(t )au EFy:
a/ Axit toluic
b/ Axit G 5 clob*nHoic
c/ Axit p 5 clob*nHoic
+/ Axit p 5 broG ph*nylax*tic
>VTH: Nguyn Ng%c $an Thanh
Trang P
Bi tp Axit caboxylic GVHD: Nguyn Th M !h"#ng
*/ Axit 1 5 broG 5 P 5 nitrob*nHoic
Bi 2: Vi@t ph"Ing trJnh Eifu ch@ axit butyric tc c'c h#p ch(t hLu cI )au:
a/ Ancol n 5 butylic
b/ Ancol n 5 propylic
c/ M*tyl n 5 propyl x*ton
Bi 3: Tc b*nH*n = axit ax*tic =Ti c'c t'c nhFn =A cI cdn thi@tM h?y teng h#p ra c'c axit:
a/ Axit 1 5 clo 5 9 5 nitrob*nHoic
b/ Axit p 5 broGb*nHoic
c/ Axit G 5 broGb*nHoic
+/ Axit 0 5 nitro 5 P 5 broGb*nHoic
Bi $: Tc axit propionic h?y Eifu ch@ c'c h#p ch(t )au:
a. Axit

- amin!r!inic
b. A"i# lac#ic
c. A"i# me#$lmalnic
Bi %: Tc ax*til*n = c'c ch(t =A cI cdn thi@tM h?y lp )I Eb teng h#p c'c ch(t )au:
a/ !ropyl propionat
b/ gtyl butirat
c/ ,)obutiraGit
+/ !ropionylclorua
Bi *: Teng h#p axit i)obutiric tc c'c ch(t )au = c'c ch(t =A cI cdn thi@t:
a/ !rop*n
b/ !ropan 5 1 5 ol
c/ 1 5 G*tylprop 5 1 5 *n
+/ Ax*til*n
Bi +: Vi@t ph"Ing trJnh Eifu ch@ axit b*nHoic tc c'c h#p ch(t hLu cI )au:
a/ Tolu*n
b/ BroG b*nH*n*
c/ Alcol b*Hylic
+/ B*nHotriclorua
*/ B*nHonitrin
Bi ,: $h teng h#p 1M 0M 9 5 tribroGb*nH*nM ng"<i ta ;hAng thh broG hDa tric ti@p =jng
b*nH*n*M G phKi xu(t ph't tc tolu*n*/ H?y =i@t )I Eb phKn Bng tr&n/
Bi -: Axit n*c=onic 3cD trong x*r*broHit c]a n?o ng"<i4 lG G(t Gu nhanh +ung +ch
VMn2
P
= +ung +ch
1
Br
trong ..l
P/
Vhk blng H
1
QNi cho axit t*tracoHanoic n 5
.
10
H
P7
.22H/ 2xi hDa axit n*c=onic trong Eifu ;imn G?nh limt cho hai axit cD ;h\i l"#ng Gol
blng 19ng = 171g/
H?y )uy ra c(u tCo c]a axit n*c=onic/
Bi 1.: .D hai ch(t Ebng phFn cD thnh phdn .
9
H
1Y
2
1
M Efu cD tonh puang hoCt/ .h(t A t'c
+Sng =Ti Na
1
.2
0
giKi phDng .2
1
= tCo Gu\i puang hoCt/ .h(t B ;hAng cD phKn Bng EDM
nh"ng ;hi Eun nDng =Ti ;ifG lCi cho Gqt trong c'c )Kn phrG l r"#u puang hoCt/ ^'c Enh
c(u tCo hai ch(t/
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