Carboxylic Acids & their derivatives : Daily Practice Problems (DPP) - 1 Class 12 Notes | EduRev

Class 12 : Carboxylic Acids & their derivatives : Daily Practice Problems (DPP) - 1 Class 12 Notes | EduRev

 Page 1


DPP- Carboxylic acids & their derivatives
SCF-07, 1
st
 floor, Sector-15, Panchkula
9217610408, 8699438881, 8699438882
            ONE CAN CONQUER THE INNERSELF WITH-
DEDICATION,DISCIPLINE & UNSHAKEABLE FAITH IN GOD
Page No.1
Some important facts & points
1. REACTIONS OF CARBOXYLIC ACID 2. ALKANOYL HALIDE (ACYL HALIDE) ?
?
?
RCOONa + 1/2H
2
RCOOH
Na
R = alkyl or aryl
RCOONa + H
2
O
RCOONa + CO
2
+ H
2
O
RCOCl + POCl
3
+ HCl
RCOCl + H
3
PO
3
RCOCl + SO
2
+ HCl
R—CH
3
R—CH
2
—OH
R—C—R + CO
2
+ H
2
O
O
NaOH
Na 2 CO 3
NaHCO 3
PCl 5
PCl 3
SOCl 2
LiAlH 4
HI/P
MnO/300
0
C
or
Ca(OH) 2 ,
N 3 H
P 2 O 5
R—N C O
(RCO) 2
O + H
2
O
NH 3 /
R' OH
R—C—OR' + H
2
O
O
RCONH
2
+ H
2
O
H
+
RCOOR'(Alcoholysis) R—C—Cl
H 2 O
Acyl chloride
RCOOC
6
H
5
RCOCN RCOCOOH
RCOOCOR
—CR
RCHO(Rosenmund' s reaction) R' OH
C 6 H 5 OH
KCN
NH 3
RCOOH
R' COONa
H 2 /Pd-BaSO 4
AlCl 3
Quinoline
—HCl
Pyridine
H 2 O/H
+
RCONH
2
(Ammonolysis) 2-oxoalkanoic acid
RCOOH
RCOOCOR' R' CdCl + RCOR' Alkyl phenyl ketone
O
—CH
2
R
Alkylbenzene
Zn-Hg/HCl
R' Cd
2
O
NaN 3
R—N C O
3. REACTIONS OF ESTER
?
RCOONa + R' OH
R—C—OR' H 2 O/H
+
RCONH
2
+ R' OH
R—C—NH—C
6
H
5
+ R' OH
R—C—R" + Mg
R—CH
2
OH + R' OH
NaOH
NH 3
C 6 H 5 NH 2
R"OH
(i) R"—MgBr
or
Na—C 2 H 5 OH
(ii) H 2 O/H
+
R—C—OR" + R' OH
R—C—OH + R' OH
(It is replacement of alkoxy part of ester with
LiAlH 4
O
O
(Saponification + irreversilbe reaction) O
the alkoxy part of alcohol and named as trans-esterification) O
OH
Br
OR' R"
R' ONa
ß-keto ester
CARBOXYLIC ACIDS
DAILY  PRACTICE  PROBLEMS
Page 2


DPP- Carboxylic acids & their derivatives
SCF-07, 1
st
 floor, Sector-15, Panchkula
9217610408, 8699438881, 8699438882
            ONE CAN CONQUER THE INNERSELF WITH-
DEDICATION,DISCIPLINE & UNSHAKEABLE FAITH IN GOD
Page No.1
Some important facts & points
1. REACTIONS OF CARBOXYLIC ACID 2. ALKANOYL HALIDE (ACYL HALIDE) ?
?
?
RCOONa + 1/2H
2
RCOOH
Na
R = alkyl or aryl
RCOONa + H
2
O
RCOONa + CO
2
+ H
2
O
RCOCl + POCl
3
+ HCl
RCOCl + H
3
PO
3
RCOCl + SO
2
+ HCl
R—CH
3
R—CH
2
—OH
R—C—R + CO
2
+ H
2
O
O
NaOH
Na 2 CO 3
NaHCO 3
PCl 5
PCl 3
SOCl 2
LiAlH 4
HI/P
MnO/300
0
C
or
Ca(OH) 2 ,
N 3 H
P 2 O 5
R—N C O
(RCO) 2
O + H
2
O
NH 3 /
R' OH
R—C—OR' + H
2
O
O
RCONH
2
+ H
2
O
H
+
RCOOR'(Alcoholysis) R—C—Cl
H 2 O
Acyl chloride
RCOOC
6
H
5
RCOCN RCOCOOH
RCOOCOR
—CR
RCHO(Rosenmund' s reaction) R' OH
C 6 H 5 OH
KCN
NH 3
RCOOH
R' COONa
H 2 /Pd-BaSO 4
AlCl 3
Quinoline
—HCl
Pyridine
H 2 O/H
+
RCONH
2
(Ammonolysis) 2-oxoalkanoic acid
RCOOH
RCOOCOR' R' CdCl + RCOR' Alkyl phenyl ketone
O
—CH
2
R
Alkylbenzene
Zn-Hg/HCl
R' Cd
2
O
NaN 3
R—N C O
3. REACTIONS OF ESTER
?
RCOONa + R' OH
R—C—OR' H 2 O/H
+
RCONH
2
+ R' OH
R—C—NH—C
6
H
5
+ R' OH
R—C—R" + Mg
R—CH
2
OH + R' OH
NaOH
NH 3
C 6 H 5 NH 2
R"OH
(i) R"—MgBr
or
Na—C 2 H 5 OH
(ii) H 2 O/H
+
R—C—OR" + R' OH
R—C—OH + R' OH
(It is replacement of alkoxy part of ester with
LiAlH 4
O
O
(Saponification + irreversilbe reaction) O
the alkoxy part of alcohol and named as trans-esterification) O
OH
Br
OR' R"
R' ONa
ß-keto ester
CARBOXYLIC ACIDS
DAILY  PRACTICE  PROBLEMS
DPP- Carboxylic acids & their derivatives
SCF-07, 1
st
 floor, Sector-15, Panchkula
9217610408, 8699438881, 8699438882
            ONE CAN CONQUER THE INNERSELF WITH-
DEDICATION,DISCIPLINE & UNSHAKEABLE FAITH IN GOD
Page No.2
4. OTHER SPECIFIC REACTIONS FOR SPECIFIC SPECIES
?
H 2 O/H
+
NaOH
or NaHCO 3
HCOOCH
3
formaldehyde
hydrogen cyanide
Na 2 CO 3
LiAlH 4
Tollen' s
reagent
K 2 Cr 2 O 7 / H
+
HCN
HCHO
CH
3
—OH
CO + NaOH
H 2 SO 4
Pt
O 2
methanol
HCOOH
Formic acid
H—COONa
HCOONa + CO
2
Ag - mirror
Cu
2
O(red ppt.) Hg
2
Cl
2
CO + H
2
O
H—CONH
2
CH
3
—OH
H 2 SO 4
CH 3 OH
Fehling' s
Solution
HgCl 2
conc. H 2 SO 4
(H) NH 3
methyl formate
sodium formate
formamide
methyl alcohol
?
?
O 2(air) H 2 O/H
+
CH
3
—COONa
PCl 5
K 2 Cr 2 O 7 / H
+
CH
3
—CH
2
—OH
CH
3
—CN
CH
3
—CHO
CH CH
H 2 SO 4 /HgSO 4
(O) CH
3
—COOH
Acetic acid
CH
3
—COONa + CO
2
(CH
3
—CO) 2
O
CH
4
C 2 H 5 OH
4(H) NaOH
Sodalime
NH 3
quick
K 2 Cr 2 O 7 / H
+
(O) oxidation
Ca(OH) 2
C
2
H
5
OH
H 2 SO 4
CH
3
—CONH
2
CH
3
COCl
CH
3
—COOC
2
H
5
CH
3
—CH
2
—OH
CH
3
—CH
3
Cl—CH
2
—COOH
CH
3
—NH
2
CH
3
COCH
3
CH
3
—CO—CH
3
H 2 SO 4
or SOCl 2
NaOH
Na 2 CO 3
or NaHCO 3
LiAlH 4
Pyroligneous acid
H 2
Red P/HI
P 2 O 5
N 3 H
Ca(OH) 2
Cl 2
P
dry distillation
MnO
300
0
C
Page 3


DPP- Carboxylic acids & their derivatives
SCF-07, 1
st
 floor, Sector-15, Panchkula
9217610408, 8699438881, 8699438882
            ONE CAN CONQUER THE INNERSELF WITH-
DEDICATION,DISCIPLINE & UNSHAKEABLE FAITH IN GOD
Page No.1
Some important facts & points
1. REACTIONS OF CARBOXYLIC ACID 2. ALKANOYL HALIDE (ACYL HALIDE) ?
?
?
RCOONa + 1/2H
2
RCOOH
Na
R = alkyl or aryl
RCOONa + H
2
O
RCOONa + CO
2
+ H
2
O
RCOCl + POCl
3
+ HCl
RCOCl + H
3
PO
3
RCOCl + SO
2
+ HCl
R—CH
3
R—CH
2
—OH
R—C—R + CO
2
+ H
2
O
O
NaOH
Na 2 CO 3
NaHCO 3
PCl 5
PCl 3
SOCl 2
LiAlH 4
HI/P
MnO/300
0
C
or
Ca(OH) 2 ,
N 3 H
P 2 O 5
R—N C O
(RCO) 2
O + H
2
O
NH 3 /
R' OH
R—C—OR' + H
2
O
O
RCONH
2
+ H
2
O
H
+
RCOOR'(Alcoholysis) R—C—Cl
H 2 O
Acyl chloride
RCOOC
6
H
5
RCOCN RCOCOOH
RCOOCOR
—CR
RCHO(Rosenmund' s reaction) R' OH
C 6 H 5 OH
KCN
NH 3
RCOOH
R' COONa
H 2 /Pd-BaSO 4
AlCl 3
Quinoline
—HCl
Pyridine
H 2 O/H
+
RCONH
2
(Ammonolysis) 2-oxoalkanoic acid
RCOOH
RCOOCOR' R' CdCl + RCOR' Alkyl phenyl ketone
O
—CH
2
R
Alkylbenzene
Zn-Hg/HCl
R' Cd
2
O
NaN 3
R—N C O
3. REACTIONS OF ESTER
?
RCOONa + R' OH
R—C—OR' H 2 O/H
+
RCONH
2
+ R' OH
R—C—NH—C
6
H
5
+ R' OH
R—C—R" + Mg
R—CH
2
OH + R' OH
NaOH
NH 3
C 6 H 5 NH 2
R"OH
(i) R"—MgBr
or
Na—C 2 H 5 OH
(ii) H 2 O/H
+
R—C—OR" + R' OH
R—C—OH + R' OH
(It is replacement of alkoxy part of ester with
LiAlH 4
O
O
(Saponification + irreversilbe reaction) O
the alkoxy part of alcohol and named as trans-esterification) O
OH
Br
OR' R"
R' ONa
ß-keto ester
CARBOXYLIC ACIDS
DAILY  PRACTICE  PROBLEMS
DPP- Carboxylic acids & their derivatives
SCF-07, 1
st
 floor, Sector-15, Panchkula
9217610408, 8699438881, 8699438882
            ONE CAN CONQUER THE INNERSELF WITH-
DEDICATION,DISCIPLINE & UNSHAKEABLE FAITH IN GOD
Page No.2
4. OTHER SPECIFIC REACTIONS FOR SPECIFIC SPECIES
?
H 2 O/H
+
NaOH
or NaHCO 3
HCOOCH
3
formaldehyde
hydrogen cyanide
Na 2 CO 3
LiAlH 4
Tollen' s
reagent
K 2 Cr 2 O 7 / H
+
HCN
HCHO
CH
3
—OH
CO + NaOH
H 2 SO 4
Pt
O 2
methanol
HCOOH
Formic acid
H—COONa
HCOONa + CO
2
Ag - mirror
Cu
2
O(red ppt.) Hg
2
Cl
2
CO + H
2
O
H—CONH
2
CH
3
—OH
H 2 SO 4
CH 3 OH
Fehling' s
Solution
HgCl 2
conc. H 2 SO 4
(H) NH 3
methyl formate
sodium formate
formamide
methyl alcohol
?
?
O 2(air) H 2 O/H
+
CH
3
—COONa
PCl 5
K 2 Cr 2 O 7 / H
+
CH
3
—CH
2
—OH
CH
3
—CN
CH
3
—CHO
CH CH
H 2 SO 4 /HgSO 4
(O) CH
3
—COOH
Acetic acid
CH
3
—COONa + CO
2
(CH
3
—CO) 2
O
CH
4
C 2 H 5 OH
4(H) NaOH
Sodalime
NH 3
quick
K 2 Cr 2 O 7 / H
+
(O) oxidation
Ca(OH) 2
C
2
H
5
OH
H 2 SO 4
CH
3
—CONH
2
CH
3
COCl
CH
3
—COOC
2
H
5
CH
3
—CH
2
—OH
CH
3
—CH
3
Cl—CH
2
—COOH
CH
3
—NH
2
CH
3
COCH
3
CH
3
—CO—CH
3
H 2 SO 4
or SOCl 2
NaOH
Na 2 CO 3
or NaHCO 3
LiAlH 4
Pyroligneous acid
H 2
Red P/HI
P 2 O 5
N 3 H
Ca(OH) 2
Cl 2
P
dry distillation
MnO
300
0
C
DPP- Carboxylic acids & their derivatives
SCF-07, 1
st
 floor, Sector-15, Panchkula
9217610408, 8699438881, 8699438882
            ONE CAN CONQUER THE INNERSELF WITH-
DEDICATION,DISCIPLINE & UNSHAKEABLE FAITH IN GOD
Page No.3
?
?
?
?
?
PCl
5
or SOCl
2
K
2
Cr
2
O
7
/ H
2
SO
4
O
CH
2
CH
3
H
+
Benzoic acid
conc. H
2
SO
4
N
3
H, H
2
SO
4
NH
3
,
H
2
O
conc. HNO
3
+ conc. H
2
SO
4
NaHCO
3
LiAlH
4
Br
2
, Fe
KMnO
4
, hot
373 K
or CrO
3
, 40% H
2
SO
4
(i) CO
2
(ii) H
3
O
+
KMnO
4
, hot
COCH
3
COOH
CH
2
CH
2
CH
3
Mg
Ether
MgBr
Br
CN
Br
COOH
m-bromobenzoic acid
NO
2
COOH
m-nitrobenzoic acid
SO
3
H
COOH
m-sulphobenzoic acid
NH
2
(Schmidt) Sodalime
CH
2
OH
CONa + CO
2
O
CNH
2
O
COC
2
H
5
(reactivity of alcohol) O
CCl
C
2
H
5
OH, H
+
(1
0
> 2
0
> 3
0
) 5. OXALIC ACID, HOOC—COOH
Chemical Nature
?
?
CO
2
+ HCOOH CO + H
2
O
Conc. H 2 SO 4
(—2H 2 O) KMnO 4 /H 2 SO 4
+ 2NH 3
NaOH
C 2 H 5 OH
—H 2 O
+4H
COOH
475K
Oxalic acid
COOH
+H 2 SO 4
CO
2
+ CO + H
2
O
COONa
COONa COONa
COOH NaOH
—H 2 O
COOC
2
H
5
COOH C 2 H 5 OH
+H 2 SO 4
COOC
2
H
5
COOC
2
H
5
(Esterification) PCl 5(Excess) COCl
COCl
+ 2POCl
3
PCl 5(1 mole) COCl
COOH
CO
2
+ CO + HCl
Zn/H 2 SO 4
CH
2
OH
COOH
(Reduction) Glycollic acid
COONH
4
COONH
4
Amm. oxalate
CONH
2
CONH
2
Oxamide
2CO
2
+ H
2
O(Pink colour of KMnO
4
solution is discharged)
Page 4


DPP- Carboxylic acids & their derivatives
SCF-07, 1
st
 floor, Sector-15, Panchkula
9217610408, 8699438881, 8699438882
            ONE CAN CONQUER THE INNERSELF WITH-
DEDICATION,DISCIPLINE & UNSHAKEABLE FAITH IN GOD
Page No.1
Some important facts & points
1. REACTIONS OF CARBOXYLIC ACID 2. ALKANOYL HALIDE (ACYL HALIDE) ?
?
?
RCOONa + 1/2H
2
RCOOH
Na
R = alkyl or aryl
RCOONa + H
2
O
RCOONa + CO
2
+ H
2
O
RCOCl + POCl
3
+ HCl
RCOCl + H
3
PO
3
RCOCl + SO
2
+ HCl
R—CH
3
R—CH
2
—OH
R—C—R + CO
2
+ H
2
O
O
NaOH
Na 2 CO 3
NaHCO 3
PCl 5
PCl 3
SOCl 2
LiAlH 4
HI/P
MnO/300
0
C
or
Ca(OH) 2 ,
N 3 H
P 2 O 5
R—N C O
(RCO) 2
O + H
2
O
NH 3 /
R' OH
R—C—OR' + H
2
O
O
RCONH
2
+ H
2
O
H
+
RCOOR'(Alcoholysis) R—C—Cl
H 2 O
Acyl chloride
RCOOC
6
H
5
RCOCN RCOCOOH
RCOOCOR
—CR
RCHO(Rosenmund' s reaction) R' OH
C 6 H 5 OH
KCN
NH 3
RCOOH
R' COONa
H 2 /Pd-BaSO 4
AlCl 3
Quinoline
—HCl
Pyridine
H 2 O/H
+
RCONH
2
(Ammonolysis) 2-oxoalkanoic acid
RCOOH
RCOOCOR' R' CdCl + RCOR' Alkyl phenyl ketone
O
—CH
2
R
Alkylbenzene
Zn-Hg/HCl
R' Cd
2
O
NaN 3
R—N C O
3. REACTIONS OF ESTER
?
RCOONa + R' OH
R—C—OR' H 2 O/H
+
RCONH
2
+ R' OH
R—C—NH—C
6
H
5
+ R' OH
R—C—R" + Mg
R—CH
2
OH + R' OH
NaOH
NH 3
C 6 H 5 NH 2
R"OH
(i) R"—MgBr
or
Na—C 2 H 5 OH
(ii) H 2 O/H
+
R—C—OR" + R' OH
R—C—OH + R' OH
(It is replacement of alkoxy part of ester with
LiAlH 4
O
O
(Saponification + irreversilbe reaction) O
the alkoxy part of alcohol and named as trans-esterification) O
OH
Br
OR' R"
R' ONa
ß-keto ester
CARBOXYLIC ACIDS
DAILY  PRACTICE  PROBLEMS
DPP- Carboxylic acids & their derivatives
SCF-07, 1
st
 floor, Sector-15, Panchkula
9217610408, 8699438881, 8699438882
            ONE CAN CONQUER THE INNERSELF WITH-
DEDICATION,DISCIPLINE & UNSHAKEABLE FAITH IN GOD
Page No.2
4. OTHER SPECIFIC REACTIONS FOR SPECIFIC SPECIES
?
H 2 O/H
+
NaOH
or NaHCO 3
HCOOCH
3
formaldehyde
hydrogen cyanide
Na 2 CO 3
LiAlH 4
Tollen' s
reagent
K 2 Cr 2 O 7 / H
+
HCN
HCHO
CH
3
—OH
CO + NaOH
H 2 SO 4
Pt
O 2
methanol
HCOOH
Formic acid
H—COONa
HCOONa + CO
2
Ag - mirror
Cu
2
O(red ppt.) Hg
2
Cl
2
CO + H
2
O
H—CONH
2
CH
3
—OH
H 2 SO 4
CH 3 OH
Fehling' s
Solution
HgCl 2
conc. H 2 SO 4
(H) NH 3
methyl formate
sodium formate
formamide
methyl alcohol
?
?
O 2(air) H 2 O/H
+
CH
3
—COONa
PCl 5
K 2 Cr 2 O 7 / H
+
CH
3
—CH
2
—OH
CH
3
—CN
CH
3
—CHO
CH CH
H 2 SO 4 /HgSO 4
(O) CH
3
—COOH
Acetic acid
CH
3
—COONa + CO
2
(CH
3
—CO) 2
O
CH
4
C 2 H 5 OH
4(H) NaOH
Sodalime
NH 3
quick
K 2 Cr 2 O 7 / H
+
(O) oxidation
Ca(OH) 2
C
2
H
5
OH
H 2 SO 4
CH
3
—CONH
2
CH
3
COCl
CH
3
—COOC
2
H
5
CH
3
—CH
2
—OH
CH
3
—CH
3
Cl—CH
2
—COOH
CH
3
—NH
2
CH
3
COCH
3
CH
3
—CO—CH
3
H 2 SO 4
or SOCl 2
NaOH
Na 2 CO 3
or NaHCO 3
LiAlH 4
Pyroligneous acid
H 2
Red P/HI
P 2 O 5
N 3 H
Ca(OH) 2
Cl 2
P
dry distillation
MnO
300
0
C
DPP- Carboxylic acids & their derivatives
SCF-07, 1
st
 floor, Sector-15, Panchkula
9217610408, 8699438881, 8699438882
            ONE CAN CONQUER THE INNERSELF WITH-
DEDICATION,DISCIPLINE & UNSHAKEABLE FAITH IN GOD
Page No.3
?
?
?
?
?
PCl
5
or SOCl
2
K
2
Cr
2
O
7
/ H
2
SO
4
O
CH
2
CH
3
H
+
Benzoic acid
conc. H
2
SO
4
N
3
H, H
2
SO
4
NH
3
,
H
2
O
conc. HNO
3
+ conc. H
2
SO
4
NaHCO
3
LiAlH
4
Br
2
, Fe
KMnO
4
, hot
373 K
or CrO
3
, 40% H
2
SO
4
(i) CO
2
(ii) H
3
O
+
KMnO
4
, hot
COCH
3
COOH
CH
2
CH
2
CH
3
Mg
Ether
MgBr
Br
CN
Br
COOH
m-bromobenzoic acid
NO
2
COOH
m-nitrobenzoic acid
SO
3
H
COOH
m-sulphobenzoic acid
NH
2
(Schmidt) Sodalime
CH
2
OH
CONa + CO
2
O
CNH
2
O
COC
2
H
5
(reactivity of alcohol) O
CCl
C
2
H
5
OH, H
+
(1
0
> 2
0
> 3
0
) 5. OXALIC ACID, HOOC—COOH
Chemical Nature
?
?
CO
2
+ HCOOH CO + H
2
O
Conc. H 2 SO 4
(—2H 2 O) KMnO 4 /H 2 SO 4
+ 2NH 3
NaOH
C 2 H 5 OH
—H 2 O
+4H
COOH
475K
Oxalic acid
COOH
+H 2 SO 4
CO
2
+ CO + H
2
O
COONa
COONa COONa
COOH NaOH
—H 2 O
COOC
2
H
5
COOH C 2 H 5 OH
+H 2 SO 4
COOC
2
H
5
COOC
2
H
5
(Esterification) PCl 5(Excess) COCl
COCl
+ 2POCl
3
PCl 5(1 mole) COCl
COOH
CO
2
+ CO + HCl
Zn/H 2 SO 4
CH
2
OH
COOH
(Reduction) Glycollic acid
COONH
4
COONH
4
Amm. oxalate
CONH
2
CONH
2
Oxamide
2CO
2
+ H
2
O(Pink colour of KMnO
4
solution is discharged) DPP- Carboxylic acids & their derivatives
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Page No.4
Objective Questions
1. Chlorination of toluene in presence of light and heat followed by treatment with aqueous NaOH gives
(a) o-Cresol (b) p-Cresol(c) 2,4-Dihydroxytoluene (d) Benzoic acid
2. What is Z in the following sequence of reaction ?
Phenol Z Y X
4 3
3
KMnO
Alkaline
AlCl . Anhyd
Cl CH
dust
Zn
- - - ? - - - ? - -- ? -(a) Benzene(b) Toluene(c) Benzaldehyde(d) Benzoic acid
3. The treatment of an ester with LiAlH
4
 followed by acid hydrolysis produces
(a) two aldehyde(b) one carboxylic acid and one alcohol
(c) two alcohols(d) two acids
4. Methylmagnesium bromide reacts with carbon dioxide. The product formed is
(a) CH
3
COCH
3
(b) CH
3
CH
2
OH(c) CH
3
CHO(d) CH
3
COOH
5. The IUPAC name for,
3
3 2 2
|
CH CH CH CH COC
CH
- - l , is
(a) 3- Methylpentanoyl chloride(b) 3-Methyl butanoyl chloride
(c) 1-Chloro-3-ethylbutanone(d) 1-Chloro-3-methylpentanone
6. The compound formed as a result of potassium permanganate oxidation of ethylbenzene is
(a) Benzoic acid(b) Benzyl alcohol(c) Benzophenone(d) Acetophenone
7. In presence of acid, hydrolysis of methyl cyanide  gives
(a) Acetic acid(b) Methylamine(c) Methyl alcohol(d) Formic acid
8. The acid formed when propyl magnesium bromide is treated with carbon dioxide is
(a) C
3
H
7
COOH(b) C
2
H
5
COOH(c) Both(d) None
9. Carboxylic acids can not be prepared by the hydrolysis of
(a) Acid amides(b) Acid chlorides(c) Acid halide(d) Alkyl halides
10. Pyruvic acid is obtained by
(a) oxidation and hydration of acetaldehyde cyanohydrin
(b) oxidation of acetone cyanohydrin
(c) oxidation of formaldehyde(d) none of these
11. Which of the following has highest solubility in water ?
(a) n-Butyric acid(b) propionic acid(c) isobutyric acid(d) Acetic acid
12. The IUPAC name of CH O
3
C
O
COOH
(a) 4-Methoxybenzoic acid(b) 4-Carboxy-methylbenzoate
(c) 4-Methoxycarbonyl -benzoic acid(d) None of these
13.
HO
O OH
OH
O O
; The IUPAC name of the above acid is
(a) Propane 1,2,3-tricarboxylic acid(b) 3-hydroxyl-1,5-pentanedioic acid
(c) 3-hydroxyl-3-keto-1,5-pentanedioic acid(d) 1,3,5-trihydroxypentane-1,5-dione
Page 5


DPP- Carboxylic acids & their derivatives
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Page No.1
Some important facts & points
1. REACTIONS OF CARBOXYLIC ACID 2. ALKANOYL HALIDE (ACYL HALIDE) ?
?
?
RCOONa + 1/2H
2
RCOOH
Na
R = alkyl or aryl
RCOONa + H
2
O
RCOONa + CO
2
+ H
2
O
RCOCl + POCl
3
+ HCl
RCOCl + H
3
PO
3
RCOCl + SO
2
+ HCl
R—CH
3
R—CH
2
—OH
R—C—R + CO
2
+ H
2
O
O
NaOH
Na 2 CO 3
NaHCO 3
PCl 5
PCl 3
SOCl 2
LiAlH 4
HI/P
MnO/300
0
C
or
Ca(OH) 2 ,
N 3 H
P 2 O 5
R—N C O
(RCO) 2
O + H
2
O
NH 3 /
R' OH
R—C—OR' + H
2
O
O
RCONH
2
+ H
2
O
H
+
RCOOR'(Alcoholysis) R—C—Cl
H 2 O
Acyl chloride
RCOOC
6
H
5
RCOCN RCOCOOH
RCOOCOR
—CR
RCHO(Rosenmund' s reaction) R' OH
C 6 H 5 OH
KCN
NH 3
RCOOH
R' COONa
H 2 /Pd-BaSO 4
AlCl 3
Quinoline
—HCl
Pyridine
H 2 O/H
+
RCONH
2
(Ammonolysis) 2-oxoalkanoic acid
RCOOH
RCOOCOR' R' CdCl + RCOR' Alkyl phenyl ketone
O
—CH
2
R
Alkylbenzene
Zn-Hg/HCl
R' Cd
2
O
NaN 3
R—N C O
3. REACTIONS OF ESTER
?
RCOONa + R' OH
R—C—OR' H 2 O/H
+
RCONH
2
+ R' OH
R—C—NH—C
6
H
5
+ R' OH
R—C—R" + Mg
R—CH
2
OH + R' OH
NaOH
NH 3
C 6 H 5 NH 2
R"OH
(i) R"—MgBr
or
Na—C 2 H 5 OH
(ii) H 2 O/H
+
R—C—OR" + R' OH
R—C—OH + R' OH
(It is replacement of alkoxy part of ester with
LiAlH 4
O
O
(Saponification + irreversilbe reaction) O
the alkoxy part of alcohol and named as trans-esterification) O
OH
Br
OR' R"
R' ONa
ß-keto ester
CARBOXYLIC ACIDS
DAILY  PRACTICE  PROBLEMS
DPP- Carboxylic acids & their derivatives
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Page No.2
4. OTHER SPECIFIC REACTIONS FOR SPECIFIC SPECIES
?
H 2 O/H
+
NaOH
or NaHCO 3
HCOOCH
3
formaldehyde
hydrogen cyanide
Na 2 CO 3
LiAlH 4
Tollen' s
reagent
K 2 Cr 2 O 7 / H
+
HCN
HCHO
CH
3
—OH
CO + NaOH
H 2 SO 4
Pt
O 2
methanol
HCOOH
Formic acid
H—COONa
HCOONa + CO
2
Ag - mirror
Cu
2
O(red ppt.) Hg
2
Cl
2
CO + H
2
O
H—CONH
2
CH
3
—OH
H 2 SO 4
CH 3 OH
Fehling' s
Solution
HgCl 2
conc. H 2 SO 4
(H) NH 3
methyl formate
sodium formate
formamide
methyl alcohol
?
?
O 2(air) H 2 O/H
+
CH
3
—COONa
PCl 5
K 2 Cr 2 O 7 / H
+
CH
3
—CH
2
—OH
CH
3
—CN
CH
3
—CHO
CH CH
H 2 SO 4 /HgSO 4
(O) CH
3
—COOH
Acetic acid
CH
3
—COONa + CO
2
(CH
3
—CO) 2
O
CH
4
C 2 H 5 OH
4(H) NaOH
Sodalime
NH 3
quick
K 2 Cr 2 O 7 / H
+
(O) oxidation
Ca(OH) 2
C
2
H
5
OH
H 2 SO 4
CH
3
—CONH
2
CH
3
COCl
CH
3
—COOC
2
H
5
CH
3
—CH
2
—OH
CH
3
—CH
3
Cl—CH
2
—COOH
CH
3
—NH
2
CH
3
COCH
3
CH
3
—CO—CH
3
H 2 SO 4
or SOCl 2
NaOH
Na 2 CO 3
or NaHCO 3
LiAlH 4
Pyroligneous acid
H 2
Red P/HI
P 2 O 5
N 3 H
Ca(OH) 2
Cl 2
P
dry distillation
MnO
300
0
C
DPP- Carboxylic acids & their derivatives
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Page No.3
?
?
?
?
?
PCl
5
or SOCl
2
K
2
Cr
2
O
7
/ H
2
SO
4
O
CH
2
CH
3
H
+
Benzoic acid
conc. H
2
SO
4
N
3
H, H
2
SO
4
NH
3
,
H
2
O
conc. HNO
3
+ conc. H
2
SO
4
NaHCO
3
LiAlH
4
Br
2
, Fe
KMnO
4
, hot
373 K
or CrO
3
, 40% H
2
SO
4
(i) CO
2
(ii) H
3
O
+
KMnO
4
, hot
COCH
3
COOH
CH
2
CH
2
CH
3
Mg
Ether
MgBr
Br
CN
Br
COOH
m-bromobenzoic acid
NO
2
COOH
m-nitrobenzoic acid
SO
3
H
COOH
m-sulphobenzoic acid
NH
2
(Schmidt) Sodalime
CH
2
OH
CONa + CO
2
O
CNH
2
O
COC
2
H
5
(reactivity of alcohol) O
CCl
C
2
H
5
OH, H
+
(1
0
> 2
0
> 3
0
) 5. OXALIC ACID, HOOC—COOH
Chemical Nature
?
?
CO
2
+ HCOOH CO + H
2
O
Conc. H 2 SO 4
(—2H 2 O) KMnO 4 /H 2 SO 4
+ 2NH 3
NaOH
C 2 H 5 OH
—H 2 O
+4H
COOH
475K
Oxalic acid
COOH
+H 2 SO 4
CO
2
+ CO + H
2
O
COONa
COONa COONa
COOH NaOH
—H 2 O
COOC
2
H
5
COOH C 2 H 5 OH
+H 2 SO 4
COOC
2
H
5
COOC
2
H
5
(Esterification) PCl 5(Excess) COCl
COCl
+ 2POCl
3
PCl 5(1 mole) COCl
COOH
CO
2
+ CO + HCl
Zn/H 2 SO 4
CH
2
OH
COOH
(Reduction) Glycollic acid
COONH
4
COONH
4
Amm. oxalate
CONH
2
CONH
2
Oxamide
2CO
2
+ H
2
O(Pink colour of KMnO
4
solution is discharged) DPP- Carboxylic acids & their derivatives
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Page No.4
Objective Questions
1. Chlorination of toluene in presence of light and heat followed by treatment with aqueous NaOH gives
(a) o-Cresol (b) p-Cresol(c) 2,4-Dihydroxytoluene (d) Benzoic acid
2. What is Z in the following sequence of reaction ?
Phenol Z Y X
4 3
3
KMnO
Alkaline
AlCl . Anhyd
Cl CH
dust
Zn
- - - ? - - - ? - -- ? -(a) Benzene(b) Toluene(c) Benzaldehyde(d) Benzoic acid
3. The treatment of an ester with LiAlH
4
 followed by acid hydrolysis produces
(a) two aldehyde(b) one carboxylic acid and one alcohol
(c) two alcohols(d) two acids
4. Methylmagnesium bromide reacts with carbon dioxide. The product formed is
(a) CH
3
COCH
3
(b) CH
3
CH
2
OH(c) CH
3
CHO(d) CH
3
COOH
5. The IUPAC name for,
3
3 2 2
|
CH CH CH CH COC
CH
- - l , is
(a) 3- Methylpentanoyl chloride(b) 3-Methyl butanoyl chloride
(c) 1-Chloro-3-ethylbutanone(d) 1-Chloro-3-methylpentanone
6. The compound formed as a result of potassium permanganate oxidation of ethylbenzene is
(a) Benzoic acid(b) Benzyl alcohol(c) Benzophenone(d) Acetophenone
7. In presence of acid, hydrolysis of methyl cyanide  gives
(a) Acetic acid(b) Methylamine(c) Methyl alcohol(d) Formic acid
8. The acid formed when propyl magnesium bromide is treated with carbon dioxide is
(a) C
3
H
7
COOH(b) C
2
H
5
COOH(c) Both(d) None
9. Carboxylic acids can not be prepared by the hydrolysis of
(a) Acid amides(b) Acid chlorides(c) Acid halide(d) Alkyl halides
10. Pyruvic acid is obtained by
(a) oxidation and hydration of acetaldehyde cyanohydrin
(b) oxidation of acetone cyanohydrin
(c) oxidation of formaldehyde(d) none of these
11. Which of the following has highest solubility in water ?
(a) n-Butyric acid(b) propionic acid(c) isobutyric acid(d) Acetic acid
12. The IUPAC name of CH O
3
C
O
COOH
(a) 4-Methoxybenzoic acid(b) 4-Carboxy-methylbenzoate
(c) 4-Methoxycarbonyl -benzoic acid(d) None of these
13.
HO
O OH
OH
O O
; The IUPAC name of the above acid is
(a) Propane 1,2,3-tricarboxylic acid(b) 3-hydroxyl-1,5-pentanedioic acid
(c) 3-hydroxyl-3-keto-1,5-pentanedioic acid(d) 1,3,5-trihydroxypentane-1,5-dione
DPP- Carboxylic acids & their derivatives
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Page No.5
14. Which of the following is the correct decreasing order of acidic strength of
(i) methanoic acid(ii) ethanoic acid(ii) propanoic acid(iv) butanoic acid
(a)(i) > (ii) > (iii) > (iv)(b)(iv) > (iii) > (ii) > (i)(c)(i) > (iv) > (iii) > (ii) (d)(iv) > (i) > (ii) > (iii) 15. The major product of nitration of benzoic acid is
(a) 3- Nitrobenzoic acid(b) 4-Nitrobenzoic acid
(c) 2-Nitrobenzoic acid(d) 2,4-Dinitrobenzoic acid
16. Reaction of ethyl formate with excess of CH
3
MgI followed by hydrolysis gives
(a) n-Propyl alcohol(b) Ethanal(c) Propanal(d) isopropyl alcohol
17. Carboxylic acid group does not give the usual addition and elimination reactions of aldehydes & ketones because
(a) O - H bond is more polar than  >C =O group(b) Carboxylate ion gets ionised
(c) Carboxylate ion gets stabilised by resonance(d) It exists as - COOH and there is no carbonyl group
18. Formic acid and acetic acid may be distinguished by reaction with
(a) Sodium(b) Mercuric chloride
(c) 2,4-Dinitrophenylhydrazine(d) Sodium ethoxide
19. The acid amide is converted into acid with evolution of nitrogen gas by
(a) HCl(b)       NaOH(c) HNO
2
   (d) P
2
O
5
20. Which one of the following esters is obtained by the esterification of propan-2-ol with ethanoic acid?
(a)(CH
3
) 2
CHCOOCH
3
(b) CH
3
COOCH
2
CH
3
(c) CH
3
COOCH(CH
3
) 2
  (d)       (CH
3
) 2
CHCOOCH
2
CH
3
21. Which of the following has the maximum acidic strength?
(a) o-Nitrobenzoic acid(b) m-Nitrobenzoic acid(c) p-Nitrobenzoic acid (d) p-Nitrophenol
22. Which of the following carboxylic acids under goes decarboxylation easily ?
(a) 6 5 2
C H CO CH COOH - - -(b) 6 5
C H CO COOH - -(c) 6 5
C H CH COOH
|
OH
- -(d) 6 5
2
C H CH COOH
|
NH
- - 23. The molecular weight of benzoic acid in benzene as determined by depression in freezing point method corresponds
to
(a) Ionization of benzoic acid(b) Dimerization of benzoic acid
(c) Trimerization of benzoic acid(d) Solution of benzoic acid
24. Which one of the following esters cannot undergo self Claisen condensation ?
(a) CH
3
–CH
2
–CH
2
–COOC
2
H
5
(b) C
6
H
5
COOC
2
H
5
(c) C
6
H
11
–CH
2
–COOC
2
H
5
(d) C
6
H
5
–CH
2
COOC
2
H
5
25. When propionic acid is treated with aqueous sodium bicarbonate, CO
2
 is liberated . The ‘C” of CO
2
 comes from
(a) methyl group(b) carboxylic acid group (c) methylene group(d) bicarbonate
26. Benzoyl chloride is prepared from benzoic acid by
(a) Cl
2
, hv(b) SO
2
Cl
2
(c) SOCl
2
(d) Cl
2
, H
2
O
27. Which of the following acids has the smallest dissociation constant ?
(a) CH
3
CHFCOOH(b) FCH
2
CH
2
COOH(c) BrCH
2
CH
2
COOH(d) CH
3
CHBrCOOH
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