ALLEN® Carboxylic Acid and Their Derivatives 1

CH3
CARBOXYLIC ACID AND
THEIR DERIVATIVES 5. {kkjh; KMnO4
¾¾¾¾¾ ® "X"
H+
1. lwph-I rFkk lwph-II dk lqesy dhft, % OCH3
lwph-I lwph-II mijksDr vfHkfØ;k ij fopkj dj mRikn "X" dks
O
(a) R–C–Cl®R–CHO (i) Br2/NaOH igpkfu, %
(b) R–CH2–COOH ®R–CH–COOH (ii) H2/Pd–BaSO4 CHO
Cl
O
(1) X-
(c) R–C–NH2®R–NH2 (iii) Zn(Hg)/lkUæ HCl
O
OCH3
(d) R–C–CH3®R–CH 2–CH 3 (iv) Cl2/yky P, H 2O
CH2OH
uhps fn, x;s fodYiksa eas ls lgh mÙkj pqfu, %

®
(1) (a)–(ii), (b)–(i), (c)–(iv), (d)–(iii) (2) X-
(2) (a)–(iii), (b)–(iv), (c)–(i), (d)–(ii)
(3) (a)–(ii), (b)–(iv), (c)–(i), (d)–(iii) OCH3
(4) (a)–(iii), (b)–(i), (c)–(iv), (d)–(ii)
COOH
2. fn, x;s vfHkfØ;k esa 'X' D;k gS ?
CH2OH (3) X-
+ vkDtsfyd vEy 210°C X
CH2OH (eq[; mRikn)
CH2 CH–OH OCH3
(1) (2) CH3
CH2 CH2
CHO CH2OH (4) X-
(3) (4)
CHO CHO
OH
CH3 COOH
"A"
3. 6. KMnO4
'A'
H2SO4, D (çeq[k mRikn)
OCH3 OCH3 KMnO4
'B'
mijksDr vfHkfØ;k esa vfHkdeZd "A" gS@gSa : H2O, 273K (çeq[k mRikn)
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(1) NaBH4, H3O+

mijksDr jklk;fud vfHkfØ;kvksa ds fy, lgh
(2) LiAlH4
(3) {kkjh; KMnO4, H+ dFku fuEufyf[kr esa ls igpkfu, :
(4) HCl, Zn-Hg (1) ;kSfxd 'A' rFkk ;kSfxd 'B' nksuksa
4. mijksDr vfHkfØ;k ij fopkj dj mRikn "A" dks
MkbdkcksZfDlfyd vEy gSA
igpkfu, %
(2) ;kSfxd 'A' rFkk ;kSfxd 'B' nksuksa MkbvkWy gSA
CH2NH2 CH2NO2

(1) (2) (3) ;kSfxd 'A' MkbvkWy gS vkSj ;kSfxd 'B'

H MkbdkcksZfDlfyd vEy gSA
CONH2 C=N—OH
(4) ;kSfxd 'A' MkbdkcksZfDlfyd vEy rFkk ;kSfxd
(3) (4)
'B' MkbvkWy gSA

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2 Carboxylic Acid and Their Derivatives ALLEN®
O 10. fuEufyf[kr vfHkfØ;k esa fojfpr eq[; mRikn gS :
NH2 COOH
7. KOBr
¾¾® A
SOCl , CH3OH
(eq[; mRikn) 2
eq[;
N NH2
Br
H mRikn
O
CO2CH3
NH2 LiAlH
B
¾¾®
H3O+ (1)
(eq[; mRikn) N NH2×HCl
Br H×HCl
mijksDr vfHkfØ;kvksa esa mRikn A rFkk mRikn B gSa] CO2M
Cl
Øe'k%
NH2 (2)
N NH2
(1) NH2
, H

®
Br CO2 CH3
NH2 (3)
(2) NH2 N NH2×HCl
, H
Br COCl
NH2 (4)
(3) NH2
, N NH2
NH2 H
(4) NH2 11. fuEufyf[kr vfHkfØ;k dk eq[; mRikn gS:
,
CH3 O
(i) alcoholic NH3
Br Br
CH3–CH–CH2–CH2–C–Cl (ii) NaOH, Br2
8. dejs ds rki ij tyvi?kVu ds fy, (iii) NaNO2,HCl eq[; mRikn
vfHkfØ;k'khyrk dk lgh Øe gS: (iv) H2O
(1) (A) > (B) > (C) > (D) Br
(2) (D) > (A) > (B) > (C)
(3) (D) > (B) > (A) > (C) (1) CH3–CH–CH–CH2OH
(4) (A) > (C) > (B) > (D) CH3
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O
(2) CH3–CH–CH2–CH2–CH2OH
9. O CH3
(3) CH3–CH–CH2–CH2OH
O
CH3
eSysbd ,ugkbMªkbM
eSysbd ,ugkbMªkbM dks fuEu eas ls fdlds }kjk (4) CH3–CH–CH2–CH2–Cl
fufeZr fd;k tk ldrk gS : CH3
(1) trans-C;wV-2-bZu Mkbvksbd vEy dks xeZ
12. fuEufyf[kr esa ls dkSu lh ,d vfHkfØ;k izksisukbd
djdsA
vEy ugha nsxh\
(2) cis-C;wV-2-bZu Mkbvksbd vEy dks xeZ djdsA
(3) cis-C;wV-2-bZu Mkbvksbd vEy dh ,sYdksgkWy (1) CH3CH2COCH3 + OI–/H3O+
rFkk vEy ls vfHkfØ;k djdsA (2) CH3CH2CH3 + KMnO4 (Heat),OH–/H3O+
(3) CH3CH2CCl3 + OH–/H3O+
(4) trans-C;wV-2-bZu Mkbvksbd vEy dh ,sYdksgkWy
(4) CH3CH2CH2Br + Mg, CO2 dry ether/H3O+
rFkk vEy ls vfHkfØ;k djdsA

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 ALLEN® Carboxylic Acid and Their Derivatives 3
13. vfHkfØ;kvksa ds fuEufyf[kr lsVksa esa eq[; mRikn
A rFkk B gSa :
OH
+
A ¬¾¾¾
LiAlH 4
H O+
¾¾
H 3O
¾® B
H 2 SO 4
3
CN

OH OH

(1) A = ,B=
OH CHO

OH OH

(2) A = ,B=
CHO CO2H

OH

®
(3) A = ,B= COOH
NH2

OH OH

(4) A = ,B=
NH2 CHO

14. vfHkfØ;kvksa ds fuEu Øe esa foor Ja[kyk

lajpuk okyk ,d ;kSfxd A (v.kq lw=k C6H12O2)
C4 dkcksZfDlfyd vEy nsrk gSA A gS %

A ¾¾¾
LiAlH4
H O+
® B ¾¾¾¾
vkWDlhdj.k
® C 4 - dkcksZfDlfyd vEy
3

(1) CH3 – CH2 – COO – CH2 – CH2 – CH3

OH
(2) CH3–CH2–CH–CH2–O–CH=CH2
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(3) CH3 – CH2 – CH2 – COO – CH2 – CH3

(4) CH3 – CH2 – CH2 – O – CH = CH – CH2 – OH

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4 Carboxylic Acid and Their Derivatives ALLEN®
SOLUTION 5. Official Ans. by NTA (3)
CH3 CO2H
1. Official Ans. by NTA (3)
alkaline KMnO 4
Sol. Match list-I & list-II Sol. ¾¾¾¾®
H +

O O
H OCH3 OCH3
(a) R–C–Cl Pd–BaSO
2
R–CH (a) – (ii) (X)
4

Rosenmund Reduction 6. Official Ans. by NTA (4)

Sol. KMnO COOH
Cl /P ¾¾®
4

(b) R–CH2–COOH H 2O R–CH–COOH H2SO4, D COOH

2
Cl
dicarboxylic acid
HVZ reaction (b)-(iv) (A)
OH
O KMnO
Br2 ¾¾¾¾® 4

(c) R–C–NH 2 R–NH2 (c) - (i) H SO , 273K

2 4

®
NaOH OH
Diol
Hoffmann Bromamide reaction
(B)
O 7. Official Ans. by NTA (4)
Zn(Hg)
(c) R–C–CH3 con. HCl R–CH2–CH3 (d) - (iii)
O
Clemmenson reduction NH2
NH2 (KOBr)
Sol.
2. Official Ans. by NTA (1)
O Br Br [A]
CH2OH COOH 110°C CH 2 C=O O
Sol. +
CH2OH COOH CH 2 C=O
O NH2 LiAlH4 NH2
D H3O+
CH2=CH2+2CO2 Br Br (B)

3. Official Ans. by NTA (3) 8. Official Ans. by NTA (1)

Sol. R–C–Cl > R–C–O–C–R >
CH3 COOH

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Sol. "A" O O O
Reactivity towards
OCH3 OCH3 Hydrolysis
CH3 COOH R–C–OR > R–C–NH2
AlkalineKMnO4
H
+ ;
O O
OCH3 OCH3 A>B>C>D
4. Official Ans. by NTA (3) 9. Official Ans. by NTA (2)
Sol. Cis but 2-enoic acid
O O
CºN C – NH2 C – OH O
H3O H3O CH – CO2H D CH – C
Sol. D O
CH – CO2H CH – C
'A' Complete
Major hydrolysis O
product Maleic anhydride
(partial hydrolysis)

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 ALLEN® Carboxylic Acid and Their Derivatives 5
10. Official Ans. by NTA (3) 13. Official Ans. by NTA (3)

Sol. Sol.

O
COOH C–Cl
SOCl2, + HCl
NH2 CH OH NH2
N 3 N
H H
+HCl CH3OH 14. Official Ans. by NTA (3)
O (A) [C6H12O2]
C–OCH3
Sol. CH3–CH2–CH2–C–O–CH2–CH3
O
NH2.HCl
N (1) LiAlH4
H (2) H3O+

11. Official Ans. by NTA (3) CH3–CH2–CH2–CH2–OH + CH3 –CH2–OH

®
(B)
O [O]
alc. NH3
Sol. CH3–CH–CH2–CH2–C–Cl
CH3–CH2–CH2–C–OH [C4 carboxylic acid]
CH3
O
CH3 O
NaOH, Br2
CH3–CH–CH2–CH2–C–NH2

NaNO2,HCl
CH3–CH–CH2–CH2–NH2
CH3
CH3–CH–CH2–CH2–N+Cl–
CH3
H2 O

CH3–CH–CH2–CH2–OH
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CH3

12. Official Ans. by NTA (4)

Sol. All gives propanoic acid as product but option 4

gives butanoic as product

Mg
CH3CH2CH2Br Dry ether CH3CH2CH2MgBr
CO2
O
CH3–CH2–CH2–C–OMgBr
H3O+
O
CH3–CH2–CH2–C–OH
Butanoic acid