NARAYANA SR AIEEE -MATERIAL 221 Carboxylic Acids

CARBOXYLIC ACIDS
 ,   NOMENCLATURE :
SYNOPSIS:
 Carbon atom attached to the functional group
INTRODUCTION AND NOMENCLATURE
carbons called  carbon, next one is 
 General Molecular formula of Saturated aliphatic carbon so on ..............
monocarboxylic acids is CnH2n+1-COOH  In common system instead of using the
numerical prefix as per IUPAC system. The
O positon of substituents are indicated by
 ||
is carboxylic acid functional
 C O H  . . etc.
group Ex.

 Most of the aliphatic mono carboxylic acid

a)
obtained by the hydrolysis of natural fats hence
they are also known are fatty acids. - methyl / propionic acid

 Higher members of aliphatic carboxylic acids

 C12  C18  . Known as fatty acids, occur in

natural fat as esters of glycerol. b)

 The common names end with the suffix - ic acid

and have been derived from latin (or) Greek names - chloro – methyl/ Butyric acid
of their natural sources.
NAMING OF AROMATIC ACIDS
Ex: Acid obtained from red ants is formic acid
(HCOOH) (Latin : Formica means – Ant)

 Acetic acid (CH3COOH) is from vinegar (Latin:  Benzene / carboxylic acid (or)
acetum means Vinegar). The chief constituent
of vineger is Acetic acid.
Benzoic aicd

 Butyric acid CH 3  CH 2  CH 2  COOH

from rancid butter (Latin : Butyrum means butter)
 2-phenyl / ethanoic acid
Naming of acids as the derivatives of acetic acid
Except formic acid i.e., methanoic acid (H-COOH)
remaining acids are named as acetic acid.

 Benzene -1, 2-dicarboxylic acid

NOMENCLATURE :
COMMON NAMES :
 Common names are derived from the the
source of particular acid.
NARAYANA SR AIEEE -MATERIAL 222 Carboxylic Acids
ACIDIC NATURE - ORDER OF ACIDIC
STRENGTH

Benzoic acid - Carboxylic acids dissociate in water to give

resonance stabilized carboxylate anions

Phenyl acetic acid -

Phthalic acid -

IUPAC SYSTEM :
IUPAC system of saturated aliphatic mono
carboxylic acids contain
a) Root word is Alk The strength of an acid is given by its P Ka
b) Primary suffix - ane value K a = -logKa where Ka=acid dissociation
c) Secondary suffix - oic acid P
constant
Hence alkanoic acid is the IUPAC name of
saturated aliphatic mono carboxylic acids Lesser the pKa value, stronger the acid
Carboxylic acids are named as Alkanoic acids. i.e.better it is as proton donor,
for strong acid have pKa < 1,
for moderately strong acids pKa 1 to 5
for weak acids pKa 5 to 15
for extreamely weak acids pKa > 15
Carboxylic acids are weaker than mineral
acids but stronger than alcohols and phenols
Carboxylic acids are most acidic organic acids

p Ka value for ethanol is 16 and for phenol
is 10
The pKa of HCl is -7.0, pKa of trifluoroacetic
acid is 0.23, (the strongest organic acid) that
of benzoic acid 4.19 and acetic acid 4.76
respectively.
Phenoxide has non equivalent resonance
structure with negative charge on relatively
more electro positive carbon.
 STRUCTURE OF CARBOXYL GROUP :
In carboxylate ion the negative charge
1) In carboxylic acids, the bonds to the carbon delocalisaion is more on electro negative
lie in one plane and are separated by about oxygen atom. Therefore carboxylic acids are
more acidic than phenol.
120 
2) The carboxylic carbon is less electrophilic than
carbonyl carbon becasue of the possible
resonance structure
NARAYANA SR AIEEE -MATERIAL 223 Carboxylic Acids
EFFECT OF SUBSTITUENS ON THE
ACIDITY OF CARBOXYLIC ACIDS : Electron
with drawing groups increase the acidity of
carboxylic acids by stabilising the carboxylate
ion, the conjugate base through delocalisation
 
of negative charge by inductive effect or
resonance effects.
Electron withdrawing group
4-methoxy / benzoic acid benzoic acid
pKa = 4.46 pKa=4.19
stabilises carboxylate ion

Ex. F, Cl
On the otherhand electron donating groups
decrease the acidity of carboxylic acids as
they destabilize the conjgute base
4-nitro benzoic acid
Electron donating group pKa = 3.41
Increasing order of acedic strength when the
carboxylic acid contains
destabilices carboxylate ion Ph < I < Br < Cl < F < CN < NO2 < CF3
decreasing order of acidic strength
Ex. OCH3 CF3COOH > CCl3COOH > CHCl2 COOH>
BrCH 2COOH > HCOOH > ClCH 2COOH>
Increase in the number of Cl atoms at  - C6H5COOH>C6H5 -CH2COOH > CH3CH2COOH
position (-I effect) increases the acidic 
strength and pKa value decrease
CCl3COOH > CHCl2COOH > CF3COOH  CCl3COOH  CHCl2COOH 
CH2ClCOOH > CH3COOH NO2  CH2COOH  NC  CH2COOH 
Increase in the distance of Cl atom from - FCH2COOH  ClCH2COOH  BrCH2COOH 
COOH group decreases the acidic strength
HCOOH  ClCH2CH2C6H5COOH  C6H5CH2COOH 
Cl Cl
| | CH3COOH  CH3CH2COOH
CH 3CH 2 C HCOOH  CH 3 C HCH 2COOH
PREPARATION METHODS OF ACETIC ACID

OXIDATION OF C2H5OH(PRIMARY ALCOHOL):

O ), K C r O  o r  K M n O
CH3-CH2-OH  (   2
   CH3CHO
H SO
2 7

2 4
4

Increase in electronegativity of halogen Ethyl alcohol Acetaldehyde

increases the acidity
CH 3COOH
2 7 
  
( O ), K C r O or K M nO
FCH2COOH  ClCH2COOH  BrCH2COOH  ICH2COOH 
2
 4
 H 2 SO4
Acetic acid
If the -COOH group is in bond with unsaturated From CO2 & CH3-Mg-Br :
carbon acidic strength increases.

HC  C  COOH  C6 H 5COOH
RMg  X  O  C  O Dry ether

CH 2  CH  COOH  CH 3COOH O


 ||
H3 O 
Electron with drawing group on C 6 H 5 of R  C  OMgx   RCOOH  MgX  OH 
aromatic carboxylic acid increases where as
electron donating groups decrease acidity O
||
O=C=O+ CH3  Mg  Br 
 CH  C  O  M gBr
3
NARAYANA SR AIEEE -MATERIAL 224 Carboxylic Acids

O
|| FROM CO2 AND GRIGANARD REAGENT :
CH  C  O  M gBr
3

 CH 3COOH +Mg(Br)OH


 H
3O

Acetic acid
HYDROLYSIS OF ALKYL CYANIDE(ALKYL
NITRILES):

 CH3CN 
Hydrolysis
CH3Cl+KCN H   or OH 

OH O
| ||
FROM ALKYL BENZENE :

CH 3  C  NH   CH 3  C  NH 2 
H O
 CH 3COOH  NH 3
2

 Aromatic carboxylic acids can be prepared by

FROM METHYL ALCOHOL AND CARBON vigorous oxidation of alkyl benzenes with
MONOXIDE chromic acid (or) acidic (or) alkaline potassium
permaganate. The entire side chain is oxidised
    
Cobalt ( or )
 CH3COOH to the carbonyl group irrespecitve of length of
CH3OH+CO Rhodium high pressure
the side chain.
Methyl alcohol Acetic Acid  Primary (or) secondary alkyl groups are
oxidised in this manner tertiary group is not
FROM ACETALDEHYDE :
effected.
1
CH 3CHO  O2 
air
Mn 2
 CH 3COOH
2
Acctaldehyde Acetic Acid

a)
BIOCHEMICAL OXIDATION OF ACETICACID:

C2H5OH 
air
 CH3COOH Toluene Benzoic acid
MicodermaAceti

Ethyl alcohol Acetic Acid

[Vinegar contains 6-10% acetic acid] b)
PREPARATION OF BENZOIC ACID
FROM AMIDES : Propylbenzene Benzoic acid

PREPARATION OF DICARBOXYLIC ACIDS:

FROM KETONE :
Benzamide Benzoic acid
FROM ESTERS :

Ethyl benzoate Benzoic acid

Benzene - 1, 4-dicarboxylic acid
NARAYANA SR AIEEE -MATERIAL 225 Carboxylic Acids
FROM BENZENE : ii)
H 2O
C 6 H 5COOCOCH 3   C 6 H 5COOH  CH 3COOH
Benzoic ethanoic Benzoicacid Ethanoicacid
anhydride

adipic acid.
 FROM ESTERS :

 PREPARATIONS METHODS :
 FROM ALCOHOL :

CH 3  CH 2 8 CH 2 OH 
CrO3  H 2SO 4
iones reagemt

1  Decanol PHYSICAL PROPERTIES :
CH 3  CH 2 8 COOH i) At ordinary temperature, acetic acid is a
colourless liquid with pungent odoured,
Decanoicacid corrosive liquid.
ii) It is miscible with water, alcohol, and ether in
 FROM NITRILES AND AMIDES : all propotions.
Nitriles are hydrolysed to amides and then to iv) It Boils at 391 K. The high Boiling point of
acids in the presence of H+ or OH- as catalyst. acetic acid in comparision to alkanes, alkyl
Mild reaction conditions are used to stop the halides or alcohols of nearly same molecular
reaction at the amide stage. masses is due to more strong hydrogen bonds
O between acetic acid molecules.This also
 
|| explains cyclic dimer formation of acetic acid
R  CN 
H or OH
H2O
 R  C NH 2 in vapour state and in aqueous state but in
liquid state it exist as polymer
 

H or H

 RCOOH
H O
CH 3CONH 2 
3
 CH 3COOH  NH 3
Ex :
Ethanamide Ethanoicacid  Aliphatic carboxylic acids upto nine carbon
atoms are colourless liquids at room
 FROM ACYLHALIDES AND ANHYDRIDES : temperature with unpleasant odours.
Acid chlorides when hydrolysed with water give  The higher acids are wax like solids and
carboxylic acids or more readily hydrolysed
odourless due to their low volatility.
with aqueous base to give carboxylic ions
which on acidification gives corresponding
 Carboxylic acids are higher boiling liquids than
aldehydes, ketones and even alcohols of
carboxylic acid.
comparable molecular masses, due to more
extensive association of carboxylic acid
molecules through intermolecular hydrogen
bonding.
 Simple aliphatic carboxylic acids having upto
H O
Ex : CH 3COCl 
2
 CH 3COOH  Cl  four carbon atoms miscible in water due
intermolecular hydrogen bonding with water.
 Anhydrides on hydrolysis gives corresponding  The solubility decreases with increasing
acid number of carbon atoms. Higher carboxylic
Ex : acids are insoluble in water due to the
increased hydrophobic interaction of
 C6 H5CO 2 O 
H O
 2C6 H5 COOH
2
3.
hydrocarbon part.
Benzoic acid, the simplest aromatic carboxylic
i)
Benzoic anhydride Benzoicacid acid is nearly insoluble in cold water.
NARAYANA SR AIEEE -MATERIAL 226 Carboxylic Acids

 Carboxylic acids are also soluble in less polar

organic solvents like benzene, ether, alcohol,
chloroform etc

CHEMICAL PROPERTIES :
ACTION WITH METALS :
2. CH3COOH + 2Na  2CH3COONa + H 2
Sodium Acetate
ACTION OF CARBONATES AND
BICARBONATES:
Na2CO3  2CH 3COOH  2CH 3COONa  CO2  H 2O
NaHCO3  CH3COOH  CH3COONa  CO2  H2O
- above reactions involves cleavage of O-H bond
ACTION WITH BASES :
Gives Corresponding Salt above reaction involves cleavage of C-OH bond
CH3COOH +NaOH  CH3COONa + H2O
Sodium acetate H.V.Z. REACTION : [  - HALOGENATION]
ACTION WITH ALCOHOL : [ESTERIFICATION]
H3O+
CH3COOH 
Re dP
Cl2
 CH2ClCOOH
CH 3 COOH + C 2 H 5OH  
 CH 3COOC 2 H 5  H 2O
Catalyst
Monochloro acetic acid
Ethyl acetate
ACTION WITH PCl3 / PCl5 /SOCl2 CH2ClCOOH 
Re dP
Cl2
 CH2Cl2COOH
3CH 3COOH  PCl3  3CH 3COCl  H 3 PO3 di-chloro acetic acid
Acetyl chloride
CH2Cl2COOH 
Re dP
 Cl3COOH
CH3COOH  PCl5  CH3COCl  POCl3  HCl Cl2

tri-chloro acetic acid

CH3COOH  SOCl2  CH3COCl  SO2  HCl
ACTION WITH NH3 : DEHYDRATION : (FORMATION OF
CH3COOH  NH3  CH3COONH4  
CH3CONH2  H2O ANHYDRIDE)
Ammonium acetate Acetamide
 P O5
O
||
O
||
2CH3COOH  2  CH  C O  C CH  H O
3 3 2

Acetic Anhydride

FORMATION OF ALKANES:
DECARBOXYLATION :

 C H 3 C O O N a  N a O H     C H 4  N a 2 C O 3
C aO
S o d a lim e 

Sodium acetate (Methane)

KOBLE’S SYNTHESIS :
Electrolysis
2CH3COONa+2H2O 


C H 3  C H 3  2 CO 2  2 KO H  H 2

at anode at cathode
NARAYANA SR AIEEE -MATERIAL 227 Carboxylic Acids
FORMATION OF CARBONYL COMPOUNDS: USES :

a)(CH3COO)2 Ca   It is a good solvent.

Calcium acetate In the preparation of acetates, acetones ,acetic

anhydride.
O
||
In the prepararation perfumes, dyes, drugs
CH 3  C  CH 3  CaCO3
For curing meat and fish;
(Acetone)
As vinegar in domestic and cooking purposes.

CH3(COO)2Ca+ (HCOO)2 Ca   i) Methanoic acid is used in rubber, textile,
Calcium acetate Calcium formate dycing, leather and electroplating industries
2CH3CHO+2CaCO3  ii) Hexanedioic acid is used in the manufacture
REDUCTION : of nylon - 6, 6
FORMATION OF ETHYL ALCOHOL:
 iii) Esters of benzoic acid are used in
LiAlH 4
CH3COOH 
 C2H5OH perfumary.
SOdium borohydride (NaBH4) doesnot reduce  iv) Sodium benzoiate is used as a food
the carboxyl group. poesesvative.
FORMATION OF ETHANE :
LEVEL - I
HI  Re d P MODELQUESTION
CH 3COOH   CH 3  CH 3
ACETIC ACID
Ni /  NOMENCLATURE
CH3COOH  3H2  CH3  CH3  2H2O
1. Which of the following can’t be named as a
OXIDATION : Prolonged Oxidation with strong derivative of CH3COOH
oxidising agents gives CO2&H2O 1) CH3CH2COOH 2) (CH3)2CHCOOH
RING SUBSTITUTION : 3) HCOOH 4) (CH3)3C-COOH
 Aromatic carboxylic acids undergo 2. The acid present in red ants is
electrophillic substitution reactions in which 1) HCOOH 2) C6H5COOH
the carboxyl group acts as a deactivating and OH
meta - directing group |
3) CH3COOH 4) C H 3  C H  C O O H
 Do not undergo Friedel - crafts reaction 3. In CH3COOH molecule, the C-C bond is formed
because the carboxyl group is deactivating by
and the catalyst AlCl3 gets bonded to the
1) sp3 - sp3 overlap 2) sp2 - sp2 overlap
carbonyl group.
3) sp - sp overlap
3 2
4) sp3 - sp overlap
4. General formula of saturated monocarboxylic
acid is

1) Cn H 2 n 1COOH 2) Cn H 2 nO2
Ex :
3) both 1 and 2 4) None

5. IUPAC name of

1) Benzoic acid
2) 2-phenyl ethanoic acid
3) Benzene 1,2 carboxyllic acid
4) 1-phenyl ethanoic acid
NARAYANA SR AIEEE -MATERIAL 228 Carboxylic Acids
6. Which of the following is a pair of functional PRACTICE QUESITONS
isomers ? (2005E) 17. Which of the following is the strongest acid
1) CH3COCH3, CH3CHO (CPMT77)
2) C2H5CO2H, CH3CO2CH3 1) CH3COOH 2) CH2ClCOOH
3) C2H5CO2H, CH3CO2C2H5 3) CHCl2COOH 4) CCl3COOH
4) CH3CO2H, CH3CHO 18. The correct order of decreasing acid strength
PRACTICE QUESTIONS of trichloroacetic acid (A), trifluoro acetic
7. A compound of general formula CnH2nO2 could acid
be (B), acetic acid (C) and formic acid (D) is
1) an acid 2) a diketone 1) ABC  D 2) AC  B D
3) an ether 4) an aldehyde 3) B  A  D  C 4) B  D  C  A
19. Which of the following orders is true regarding
8. IUPAC name of  - Chloro -  -methyl butyric
the acidic nature of COOH?
aicd 1) Formic acid > Acetic acid > Propanoic acid
1. 3-chloro-2 methyl Butanoic acid 2) Formic acid > Acetic acid < Propanoic acid
2. 2-chloro-3-methyl Butanoic acid 3) Formic acid < Acetic acid < propanoic acid
3. 2-chloro-3- methyl-Butan-4-acid 4) Formic acid < Acetic acid >Propanoic acid
4. 3-chloro-isopentanoic acid MODEL QUESTIONS
9. The carboxylic acid includes the functional PREPARATION
groups
1) carbonyl and amine groups 20. Which of the following can’t form CH3COOH
2) carbonyl and hydroxyl groups from C2H5OH
3) hydroxyl and carboxyl groups A) PCC B) PDC
4) carboxyl, hydroxyl and Alkyl groups C) K2Cr2O7 / H+ D) MICODERMA ACETI
10. The IUPAC name for methyl acetate is 1) A and B only 2) C and D only
1) Ethoxymethane 2) methyl ethanoate 3) Only A 4) All A,B,C,D
3) ethylmethanoate 4) methoxy ethane
21. CH3Cl 
KCN
A ;
11. Functional group in saturated carboxylic acid
is H 3O 
A   B (Final product) In this reaction
 C| |  ‘B’ is
1) COOH 2)
O 1) CH3COOC2H5 2) CH3COOH
3) -OH 4) None 3) HCOOH 4) CH3CONH2
12. Which of the following is called ethanoic acid
22. CH3OH  (i ) X
 CH3COOH. In this reaction
1) HCOOH 2) CH3COOH ( ii ) Rh ; 

‘X’ is
3) CH3CH2COOH 4)  CH 3 3 CCOOH 1) CO2 2) CO 3) MgO 4)C
13. IUPAC name of CH3COOC2H5
1) Methyl propionate 2) Ethyl ethanoate 23. . What is A ?
3) Aceto ethane 4) Ethoxy ethane
14. Common name of CH3CH2COOH 1) C6 H 6 2) C6 H 5COOH
1) Propionic acid 2) Butyric acid
3) Vinegar 4) Methanoic acid 3) C6 H 5 NH 2 4) C6 H 5CN
MODEL QUESTIONS
PRACTICE QUESTIONS
ACIDIC NATURE

15. The weakest acid among the following is 24. CH3-Mg-Br+CO2 X 
H 3O
 Y. In this reaction
1) CH3COOH 2) CH3CH2COOH ‘Y’ is
3) (CH3)2CHCOOH 4) (CH3)3C COOH
1) HCOOH 2) CH3COOH
16. The weeker acid among the following is
3) C2H5COOH 4) HCHO
1) CH 3COOH 2) ClCH 2COOH 25. Methyl cyanide on hydrolysis gives following
1) Acetic acid 2) Acetaldehyde
3) Cl3COOH 4)  CH 3 2 CHCOOH 3) Acetone 4) Methyl amine
NARAYANA SR AIEEE -MATERIAL 229 Carboxylic Acids

CH3CH2OH+O2  x
26.  Vinegar, In this reaction 34. Which of the following reduces carboxylic acid
‘X’ is directly to primary alcohols (CPMT1977)
1)(CH3COO)2Mn 2)CH3COOH 1) LiAIH4 2) Na + C2H5OH
3) Micoderma Aceti 4) K2Cr2O7/H  3) Lindlars Catalyst 4) H2
27. Organic esters on hydrolysis yield 35. Which reagent can convert acetic acid into
ethanol ?
1) alcohols 2) carboxylic acids
3) ethers 4) both 1 & 2 1) Sn + HCl 2) H2 + Pt
28. Which of the following acid is present in 3) LiAlH4 + ether 4) Na + Alcohol
vinegar (CPMT97) 36. An organic compound A gives effervescenses
1) Hydrochloric acid 2) Acetic Acid on treatment with aqueous saturated sodium
3) Tartaric acid 4) Citric acid bicarbonate. ‘A’ can be
 1) An alkane 2) An alkyl halide
29. C6 H 5COOC2 H 5 
H 3O

 A  C2 H 5OH , 3) A carboxylic acid 4) A ketone
What is A ? 37. An organic compound reacts (i) with metallic
sodium to liberate hydrogen and (ii) with
1) C6 H 6 2) C6 H 5 NH 2 Na2CO3 solution to liberate CO2. The compound
is (1998E)
3) C6 H 5C2 H 5 4) C6 H 5COOH 1) an alcohol 2) a craboxylic acid
MODEL QUESTIONS 3) an ether 4) an ester
PROPERTIES : PRACTICE QUESTIONS
30. Which of the following has highest boiling 38. Number of hydrogen bonds present between
point? two acetic acid molecules when they are
existing as dimers
1) C2 H 5OH 2) CH 3COOH
1) 1 2) 0 3) 3 4) 2
3) CH 3COCH 3 4) HCOOCH 3 39. Which compound will give brisk effervescence
O of CO2 on treatment with NaHCO3 ?
31.
||
Fruity smell 1) ethyl alcohol 2) acetaldehyde
CH 3  C  O H  X  3) acetone 4) acetic acid
compound. Then ‘X’ is 40. Which part of - COOH group is involved in the
1) Aldehyde 2) Chloroform reaction of acid with metals ?
3) Alcohol 4) Base O
||
1) group 2) only -OH group
32. The products formed when PCl5 reacts with C
acetic acid are 3) COOH group 4) all carboxylic group
41. Acetic acid reacts with ethanol in the presence
1) CH 3COCl , H 3 PO3 of H2SO4 to form ‘X’ and water. Which of the
following is ‘X’?(2000M)
2) CH 3COCl , H 3 PO4
1) CH3CH2COOC2H5 2) CH3COCH3
3) CH 3COCl , HCl 3) CH3COC2H5 4) CH3COOC2H5

4) CH3COCl, POCl3 , HCl 42. CH 3 - COOH  CH 3 COCl

33. Which of the following will give readily a Here the reagent is
hydrocarbon ? 1) Cl2 2) Red P + Cl2
3) CHCl3 4) PCl5
1) R - COOK 
 electrolysis
43. Acetic acid exists in a dimer state in benzene
due to (CPMT87)
2) RCOO Ag  
2 l
1) condensation reaction
2) hydrogen bonding
3) CH3CH3 
2 l / hv
3) presence of carbonyl group
4) (CH3)2 CCl2  
2 5 C H OH 4) presence of a - hydrogen
NARAYANA SR AIEEE -MATERIAL 230 Carboxylic Acids
44. W hich hydrogen atom of acetic acid is 54. The reagent used for converting ethanoic acid
replaced by Cl2 in presence of P ? to ethanol is (1996E)
1)  - hydrogen 1) LiAIH4 2) BH3
2)carboxylic hydrogen 3) PCl3 4) K2Cr2O7/H+
3) both 55. Acetyl chloride can’t be obtained from Acetic
4) oxygen of carboxy group acid with following reagent.
45. Acetic acid reacts with PCl5 to form(1998E) 1) PCl3 2) PCl5
1) LiAIH4 2) CHCl2COOH 3) SOCl2 4) S 2Cl2
3) CH3COCI 4) CH3COOCI 56. Carboxylic acids dissolve in aq. NaOH
46. In the following reaction, X and Y are because the acids undergo
respectively : 1) Protonation 2) Deprotonation
3) Carboxylation 4) Decarboxylation
CH3COOH+NH3  X 

 Y+H2O (2002E) 57. In the preparation of an ester the commonly
1) CH3CONH2,CH4 used dehydration agent is
2) CH3COONH4,CH3CONH2 1) Phosphorus pentoxide
3) CH3CONH2, CH3COOH 2) Anhydrous calcium chloride
3) Anhydrous aluminium chloride
4) CH3NH2,CH3CONH2
4) Concentrated sulphuric acid
47. Acetic acid in warming with Cl2 in the presence
58. What is the reagent used in the preparation of
of red P gives
chloroacetic acid from acetic acid ? (2001M)
1) CH3COCl 2) CH3CH2Cl
1) PCl5 2) Cl2 / red P 3) PCl3 4) SOCl2
3) Cl3C.COOH 4) CH3.COOCl
48. The - COONa group can be replaced by H 59. Which of the following converts acetic acid to
acetyl chloride ?(2000E)
atom on reaction with
1) Zn + HCl 2) H2 / Ni 1) NaCl 2) HCl 3) Cl2/P 4) PCl3
60. Which of the following compounds does not have
3) Soda lime 4) Br2+dil.NaOH
a carboxyl group?
49. By passing acetic acid vapour over calcium
1) Methanoic acid 2) Ethanoic acid
hydroxide at 600K, we get
3) Picric acid 4) Benzoic acid
1) ethanol 2) acetaldehyde
61. The COOH group in benzene ring is
3) acetone 4) acetic anhydride
50. RCOOH  RCH2OH. This mode of reduction 1) ortho directing 2) para directing
3) ortho and para directing 4) meta directing
of an acid to alcohol can be effected only by
1) Zn/HCl 2) Na - alcohol LEVEL-II
MODEL QUESTIONS
3) Aluminium isopropoxide and isopropyl
NOMENCLATURE :
alcohol
4) LiAlH4
62. Which of the following is extracted from the
P4O10 roots of valerian plant ?
51. CH3COOH  
X . In this reaction ‘X’ is
1) CH3COCl 2)CH3CONH2 1) CH 3   CH 2 3  COOH
3) (CH3CO)2O 4) CH3COOC2H5
52. Sodium Salt of Acetic acid is converted into 2) CH 3  CH 2  COOH
methane by
1) dehydrogenation 2) decarboxylation 3) CH 3   CH 2 2  COOH
3) polymerization 4) dehydration
53. The - COOH group in a carboxylic acid can 4) CH 3   CH 2 4  COOH
be replaced by ‘H’ atom by heating the acid PRACTICE QUESTIONS
with 63. Which is false about acetic acid
1) Zn with HCl 1) it is a polar molecule
2) H2 in presence of nickel 2) it forms H bonds
3) Sodalime 3) it is stronger than mineral acids
4) it has higher boiling point than
4) Bromine and concentrated aqueous alkali
corresponding alcohols.
NARAYANA SR AIEEE -MATERIAL 231 Carboxylic Acids
70. Which of the following sequences is correct?
MODEL QUESTIONS
ACIDIC NATURE 1) pK a  p  O2 NC6 H 4 COOH   pK a
64. Order of decreasing acidity of (I) HCOOH
(II) CH3COOH (III) Cl2CHCOOH (IV)  C H COOH   pK  p  HOC H COOH 
6 5 a 6 4
CF3COOH is
1) IV > III > II > I 2) IV > III > I > II 2) pK a  p  O2 NC6 H 4 COOH   pK a
3) III > IV > II > I 4) I > IV > II > III
65. Which of the following is the strongest acid
 C H COOH  
6 5
pK a  p  HOC6 H 4 COOH 
(PMT1990)
3) pK a  p  O2 NC6 H 4 COOH   pK a
1) HCOOH (pKa=3.77)
2) C6H5COOH (pKa=4.22)  C H COOH  
6 5
pK a  p  HOC6 H 4 COOH 
3) CH3COOH (pKa=4.71)
4) pK a  p  O2 NC6 H 4 COOH   pK a
4) CH3CH2COOH (pKa=4.88)
PRACTICE QUESTIONS
 C H COOH   pK  p  HOC H COOH 
6 5 a 6 4
66. Which of the following decresing order of acidic
MODEL QUESTIONS
strength of (I) methanoic acid, (II) ethanoic
PREPARATION
acid, (III) propanoic acid, (IV) butanoic acid, is 71. Assertion (A) : CH3CN on hydrolysis gives
correct ? Acetic Acid
1) I > II > III > IV 2) IV > III > II > I Reason (R) : Cyanides on hydrolysis liberates
‘NH3’ gas
3) I > IV > III > II 4) IV > I > II > III
1. Both ‘A’ and ‘R’ ae true and ‘R’ is the
67. The decreasing strength of the acids are correct explanation of A
1) CHCl2COOH > CH2ClCOOH > CH3COOH 2. Both ‘A’ and ‘R’ are true and ‘R’ is not
the correct explanation of A
2) CH3COOH > CH2ClCOOH > CHCl2COOH 3. ‘A’ is true but ‘R’ is false
3) CH2ClCOOH > CHCl2COOH > CH3COOH 4. ‘A’ is false but ‘R’ is true.
4) CH2Cl2COOH > CH3COOH > CHCl2COOH 72. In the manufacture of acetic acid from aerial
oxidation of acetaldehyde, the catalyst used
68. The correct order of increasing acidic strength is
of the following acids is 1) acidified K2Cr2O7 2) (CH3COO)2 Mn
3) HgSO4 4) Ni

PRACTICE QUESTIONS
73. The reaction of CH3MgBr on dry ice followed
I II III by acid hydrolysis gives (CPMT83)
1) I < II < III 2) I < III < II 1) acetic acid 2) formic acid
3) III < II < I 4) II < III < I 3) acetone 4) acetaldehyde
74. When ethane nitrile is hydrolysed the product
69. Which of the following orders is true regarding
formed is
the acetic nature of monosubstituted acetic acid? 1) CH3COOH 2) C2H5COOH
1) Fluoroacetic acid > Chloroacetic acid > 3) CH3CONH2 4) C2H2NH2
Bromoacetic acid KMnO4 / KOH / H 3O
75. Toluene   A. What is A?
2) Fluoroacetic acid < Chloroacetic acid < 1) Acetice acid 2) Benzene
Bromoacetic acid 3) Benzoic acid 4) Benzaldehyde.
3) Fluoroacetic acid < Chloroacetic acid >
Bromoacetic acid 76. A. What is A?
4) Fluoroacetic acid < Chloroacetic acid <
Bromoacetic acid 1) Oxalic acid 2) Malonic acid
3) Succenic acid 4) Adipic acid
NARAYANA SR AIEEE -MATERIAL 232 Carboxylic Acids
77. In vinegar the concentration of acetic acid is 85. When propionic acid is treated with aqueous
nearly
sodium bicarbonate, CO2 is liberated. The C
1) 5% 2) 2% 3) 6-10% 4) 100%
78. Methyl magnesium chloride is treated with from CO2 comes from
carbondioxide and hydrolysed, the product is
1) methyl group 2) carboxylic acid group
1) ethyl alcohol 2) diethyl carbonate 3) methylene group 4) bicarbonate
3) acetic acid 4) propanoic acid
LEVEL - III
MODEL QUESTIONS MODEL QUESTIONS
PROPERTIES
79. Acid hydrolysis of X yields two different
86. CH3-Mg-Br+CO 2  X 
H 3O 
 Y. In this
organic compounds. W hich one of the reaction ‘Y’ is
following is X ? (2003E) 1.HCOOH 2. CH3COOH
1) CH3COOH 2)CH3CONH2 3. C2H5COOH 4. HCHO
87. The increasing order of acid strength in the
3) CH3COOC2H5 4) (CH3CO)2O
a c i d s C l C H 2C O O H , C H 3C H 2C O O H ,
80. Which of the following reaction is not the
ClCH 2 CH 3 COOH,(CH 3 ) 2 CHCOOH and
oxidation ?
1) CH3 - CHO  CH3COOH CH3COOH is
2) C2H5OH  CH3 - CHO 1) (CH 3 ) 2 CHCOOH < CH 3 CH 2 COOH <
ClCH2CH2COOH < CH3COOH < ClCH2COOH
3) C2H5OH  CH3 - COOH
2) CH 3 CH 2 COOH <(CH 3 ) 2 CHCOOH <
4) CH3COOH  C2H5OH
PRACTICE QUESTIONS ClCH2CH2COOH < CH3COOH < ClCH2COOH
81. In the   halogenation of aliphatic acids 3) (CH 3 ) 2 CHCOOH < CH 3 CH 2 COOH <
(HVZ reaction) the catalyst used is ClCH 2 CH 2 COOH < ClCH 2 CH 2 COOH <
CH3COOH
1) Zn 2) P 4) (CH 3) 2CHCOOH < ClCH 2CH 2COOH <
3) FeCl3 4) AlCl3 CH3CH2COOH <CH3COOH< ClCH2CH2COOH
82. Which of the following will not undergo Hell 88. Both the organic compounds A and B can
Volhard Zelinsky reaction release hydrogen with Na. Only compound A
can form a salt with NaOH, whereas B cannot.
1) CH 3COOH
W hen A reacts with B in presence of
2) CH 3CH 2COOH con.H2SO4, a pleasant smelling compound is
3) 2,2-dimethyl propionic acid formed. The pair of compounds A and B can
4) 2-methyl propionic acid be respectively
83. The relative order of esterification of acids is 1) C2H5OH and C2H2
1) 2) CH3COOH and C2H2
3) CH3COOH and C2H5OH
2)
4) C2H5OH and CH3COOH
3)
CH3Cl + KCN ------------> ‘X’ 
 'Y '
Hydrolysis
89.
4)
84. Which of the following reagent/solution can be

P2O5
Z
used to distinguish between methanoic acid and In the above series of reaction ‘Z’ is
ethanioc acid? 1) CH3CN 2) CH3COOH
1) Tollens reagent 3) (CH3CO)2O 4) CH3-CH2-OH
2) FeCl3 solution 90. 2.3 gm Na is added to 6 gm of CH3COOH.
The Volume of ‘H2’ gas liberated at S.T.P.
3) NaOH solution 1) 1.12 lit 2) 2.24 lt
3) 3.36 lit 4) 4.48 lit
4) Na2CO3 solution
NARAYANA SR AIEEE -MATERIAL 233 Carboxylic Acids
91. Two isomeric compounds A and B have the 98. The order of increasing acid strength is
formula C2H4O2. Among them only B give brisk 1) C2H5OH < C6H5OH < CH3COOH < HCOOH
effervescence with NaHCO3 solution. Then A
2) C2H5OH < HCOOH < CH3COOH < C6H5OH
and B are
3) C2H5OH < HCOOH < C6H5OH < CH3COOH
1) HCOOCH3 , CH3COOH
4) C2H5OH < C6H5OH < HCOOH < CH3COOH
2) HCOOCH 3 , CH3CH2OH 99. Acetic acid is obtained when (IIT97)
3) CH3COOH , HCOOCH3 1)methyl alcohol is oxidised with KMnO4.
4) HCOOH , CH3COOH
2)calcium acetate is distilled in presence of
C2H5Cl 
aqKOH
92. 
A calcium formate
CH3COOH+A  B. IUPAC name of ‘B’ 3) acetaldehyde is oxidised with K2Cr2O7 and
1) Ethyl propanoate H2SO4.
2) Ethyl accetate 4) glycerol is heated with H2SO4.
3) Ethyl ethanoate 100. The following one doesnot liberates
4) Ethyl methanoate hydrogen with Sodium metal
93. The product ‘C’ in the following reaction is 1) C2H2 2) C2H5OH
(IIT1985) 3) CH3COOH 4) CH 3CHO
101. The organic compouds A and B react with
(A) (B)  (C)
heat P O ,heat
RCOOH 
NH3 2 5
sodium metal and release H2 gas. A and B
1) RNH2 2) RCN 3) RNC 4) RCONH2 react with each other to given ethyl acetate.
Then A and B are
94.
CH 3COOH 
LiAlH 4
 A 
Ni
H2
B 1) CH 3COOH and C2 H 5OH
In this reaction A and B respectively are
1. CH3OH & CH4 2. C2H5OH & C2H6 2) HCOOH and C2 H 5OH
3. CH3CHO & C2H5 OC2H5
3) CH 3COOH and CH 3OH
4. C2H5OH & CH3OCH3
4) CH 3COOH and HCOOH
95. CH 3 COOH 
4
A LiAIH

H 2 SO4
1700 C
B
102. In the reaction sequence,

S2 Cl2
 C . Then ‘C’ is


1) Tear Gas 2) War Gas C2H5Cl +KCN 

C2 H 5OH
 x 
H 3O

y
3) Cooking gas 4) Water Gas What is the molecular formula of Y ? (2003E)
1) C3H6O2 2) C3H5N 3) C2H4O 2 4) C2H6O
PRACTICE QUESTIONS
103. Oxidation product of ‘X’ with molecular formula
96. Which one of the following has maximum acid
C2H4O is Y with molecular formula C2H4O2.
strength
1) o-nitrobenzoic acid 2) m-nitrobenzoic acid The compound Y is
3) p-nitrobenzoic acid 4) p-nitrophenol 1) acetic acid 2) formic acid
2
97. C 2 H 2 +H 2 O Hg /H 3) propionic acid 4) buteric acid
 A
104. Acetic acid is reacted with metallic sodium to
A 
(O)
B form hydrogen and “X”. When ‘X’ is heated with
K Cr O7 H SO 
CPCl3
In
2 2 2 4 soda lime, ‘Y’ and sodium carbonate are
the above series of reaction ‘C’ is formed. ‘Y’ is (2001E)
1) CH3-CH2-OH 2) CH3COOH
1) C2 H 6COOH 2) CH4
3) CH3COCl 4) (CH3CO)2O
3) CH3COONa 4) CH3CONH2
NARAYANA SR AIEEE -MATERIAL 234 Carboxylic Acids

105. When ethanoic acid is treated with aqueous 113. The - COOH group in a carboxylic acid can
NaHCO3, CO2 is liberated. The ‘C’ of CO2 be replaced by ‘H’ by heating the acid with :
comes from (IIT1999) 1) Zn with HCl
2) H2in presence of nickel
1) methyl group 3) Soda - lime
2) carboxylic acid group 4) Bromine and concentrated aqueous alkali
3) methylene group 4) bicarbonate 114. Which on oxidation will not give a carboxylic
acid with the same number of carbon atoms?
106. Compounds X and Y give effervescence with
Na2CO3 solution. X gives a white prepcipitate 1) CH 3COCH 3 2) CCl3CH 2CHO
with ammonical AgNO3 while Y given a sweet
3) CH 3CH 2CH 2OH 4) CH 3CH 2CH 2O
smelling compound on heating with alcohol. X
115. Acetic acid vapours when passed over
and Y are
aluminium phosphate forms:
1) HCOOH and CH3COOH
2) CH3CHO and CH3COOH 1) CH 3CHO 2) Ketene
3) CH3COOH ad CH3COCH3 3) C2 H 6 4) C2 H 4
4) CH3COCH3 and HCOOH
116. The treatment of CH 3CH 2COOH with chlo
107. In the esterification of alcohol
rine in the presence of phosphorus gives
1) H from alcohol and OH from acid is
removed as water. 1) CH 3CH 2COCl
2) OH is replaced by CH3COO group 2) CH 3CH 2CH 3Cl
3) H is replaced by chlorine
4) H is replaced by sodium metal 3) CH 3CH  Cl  COOH
108. Which part of the -COOH group gets cleaved
4) CH 3  Cl  CH 2COOH
in the esterification with alcohol ?
1) only H atom 2) only OH part LEVEL-IV
MODEL QUESTIONS
3) either 1 or 2 4) C - OH bond
117. The conversion of -COOH group to - NH 2 group
109. Which of the following is not a derivative of
carboxylic acids ? can be made by :
1) Wurtz reaction 2) Claisen condesation
1) anhydrides 2) esters
3) Stephen’s reduction 4) Schmidt reaction
3) amines 4) amides
110. On hydrolysis an ester gave a carboxylic acid.
The potassium salt of that acid on Kolbe’s 118. Acetic acid is obtained when:
electrolysis gave ethane. That ester is 1) Glycerol is heated with sulphuric acid
1) methyl ethanoate 2) Methyl alcohol is oxidized with potassium
2) methyl methanoate permanganate
3) ethyl methanoate 3) Acetaldehyde is oxidized with potassium
4) ethyl propanoate dichromate and sulphuric acid
111. Consider the following reactions 4) Calcium acetate is distilled in presence
CaCO3 Heat of celcium formate
CH 3COOH   A  B
119. Hydrogenation of C6 H 5CHOHCOOH over
compound B is
1) an ether 2) an alcohol Rh- Al2O3 catalyst in methanol gives:
3) an aldehyde 4) a ketone
112. The percentage of carbon in the product 1) C6 H 5CH 2COOH
formed when acetic acid reacts with hydrogen
in the presence of Nickel under pressure at 2) C6 H11CHOHCOOH
elevated temperature is
3) C6 H 5CHOHCH 2OH
1) 75% 2) 80% 3) 90 % 4) 70 %
4) C6 H11CH 2COOH
NARAYANA SR AIEEE -MATERIAL 235 Carboxylic Acids
120. Which of the following carboxylic acids PRACTICE QUESTIONS
undergoes decarboxylation easily? 128. Consider the following reaction:
1) C6 H 5  CO  CH 2COOH
CH 3 Br  Mg 
Ether
A
2) C6 H 5  CO  COOH

HCHO
 B 
HOH
C
compound C is:
3) 1) Acetic acid 2) Acetaldehyde
3) Ethyl alcohol 4) Formic acid
129.  - chloropropanoic acid on treatment with
4) alcoholic
KOH followed by acidification gives:
121. The product C of the reaction,
 1) CH 3  CH  OH   COOH
CH 3CN 
H 2O
 A 
NH 3
 B   C is
1) Methyl amine 2) Ammonium acetate 2) C H 2  CH  COOH
3) Ethyl amine 4) Acetamide
122. Consider the following reactions, 3) HO  CH 2  CH 2  COOH
CH 3COOH  A 
B
CaCO3 Heat
4) CH 3  CH 2  COOH
compound B is
1) An ether 2) An alcohol 130. Acetic acid on warming with hydrazoic acid
3) An aldehyde 4) A ketone in presence of conc. H 2 SO4 gives:
123. A silver salt of fatty acid on heating with an
alkyl halide gives: 1) CH 3CONH 2
1) Ether 2) Alcohol
3) Aldehyde 4) Ester 2) CH 3 NH 2
124. Name the end product in the following series
of reactions, 3) CH 3COONH 4

CH 3COOH 
NH 3
 A   B 
P2O5
C 4) CH 3CH 2 NH 2
131. Identity Z in the sequence,
1) CH 4 2) CH 3OH
3) Acetonitrile 4) Ammonium acetate
 
H 2O H 
125. CH 3CH 2COOH  X 
Y Cl2 Alc CH 3COO NH 4 
1. Heat
2. P2 O5
 Y 
Z :
Fe KOH
the compound Y is:
1) CH 3CH 2OH 2) CH 3CH 2CN 1)

3) CH 2  CHCOOH 4) CH 2CHClCOOH 2) CH 3CN

126. The main reason for the fact that carboxylic
3) CH 3COOH
acids can undergo ionization is:
1) Absence of  -H atom 4)  CH 3CO 2 O
2) Resonance stabilization of carboxylate ion
3) High reactivity bonding 132 CH 3 CH 2 CH 2 CH 2 OH 
x
 CH 3CH 2 CH 2 COOH .
4) Hydrogen fumaric acids: here ‘x’ is known as Jones reagent then x formula
127. Carboxylic acids react with diazomenthane to is
yield : 2) K 2 Cr2 O7 / H 
1) KMnO4 / OH 
1) Amines 2) Alcohols
3) Esters 4) Amides
3) CrO3  H 2 SO4 4) KMnO4 / OH 
NARAYANA SR AIEEE -MATERIAL 236 Carboxylic Acids

136.
133
CH 3CH 2CH 2CHO 
X
 CH 3CH 2CH 2COOH
Bu tan al Bu tan oic acid
In the above reaction ‘X’ is an oxidising agent
and X is
1) Tollen’s reagent 2) Fehlings’ reagent
3) H NO3 4) All the above
137.
i In the above sequence of reactions, C is

In the above sequence of reactions, ‘C’ is the

1) 2) main product then ‘C’ is

1) 2)

3) 4)
3) 4)

138.

134.

In the above sequence of reaction, B is

, In the above reactions

1) 2)

1) HCOOH 2)

3) 4) 3) 4)

139.
135.

B is a Carbonyl Compound, then B is

1) 2)
1) 2)

3) 4)
3) 4)
NARAYANA SR AIEEE -MATERIAL 237 Carboxylic Acids
143. On vigorous oxidaton by permanganate
140. An organic compound (A) with molecular solution. [AIEEE-2002]
C6 H 6 is on treating with CH 3Cl in
formula
 CH 3 2 C  CH  CH 2  CHO gives
presence of anhydrocs AlCl3 gives B.
Which on treating with nitration mixture gives

C as a major compound ‘C’ on reacting with

K 2Cr2O7 / H 2 SO4 results into D. Then the 1)

compound D is

1) 2)
2)

3) 4)

3)
141.

In the above sequence of reactions, D is

4)

1)
144. When CH2 CHCOOH is recduced with

L iA IH 4 the compound obtained will

2)
be[AIEEE-2003]

1) CH 2  CH  CH 2OH
3)
2) CH 3  CH 2  CH 2OH

3) CH3  CH 2  CHO
4)
4) CH3  CH 2  COOH
Clalc.KOH 145. Among the following acids which has the
CH 3CH 2COOH 
redP  A 
2
 B.
142. lowest pKa value? [AIEEE-2005]

whatis B?[AIEEE-2002] 1) CH 3CH 2COOH

1) CH 3CH 2COCl 2)  CH 3 2 CH  COOH

2) CH 3CH 2CHO 3) HCOOH

3) CH 2  CHCOOH 4) CH 3COOH
4) CH 3CH 2CH 2COOH .
NARAYANA SR AIEEE -MATERIAL 238 Carboxylic Acids
146. P -cresol reacts with chloroform in alkaline 151. In a set of the given reactions, acetic acid yields
medium to give the compound A which adds a product C:
hydrogen cyanide to form, the compound B. The
latter on acidic hydrolysis gives chiral carboxylic CH3COOH  PCl5  A 
C6H6
Anhy. AlCl3
B 
C2 H5MgBr
Ether
C
acid. The structure of the carboxylicacid is
[AIEEE-2005] 1) C6 H 5COCH 3
2) C6 H 5C  Cl  CH 3  C2 H 5
3) CH 3COCl 4) C6 H 5 .C  OH  C2 H 5  CH 3
152. A sequential reaction may be performed as
1) 2) represented below:
 1   2
R CH 2CO2 H   R CH 2CO Cl 
NH  R CH 2CO NH 2
3
  3  
4  5
  R CH 2 NH 2   R CO2 H   R CH 2OH
The appropriate reagent for step (3) is:
1) Bromine alone 2) Bromine and alkali
3) HBr 4) P2O5
3) 4) 153. In the given reaction final compoind C is

147. The correct order of increasing acid strenght of

the compounds. [AIEEE-2006]
A) CH 3CO2 H B) Me OCH 2 CO2 H 1) 2)

C) CF3CO2 H D)
3) 4)

1) D  A BC 2) A D BC 154. Identify the final product CO of the following

reaction
3) B  D  AC 4) D  AC  B
148. Lactic acid on oxidation with Fenton’s
reagent gives main product:
1) CH 3COOH 2) H 2C2O4
3) CH 3COCOOH 4) none of these
149. Hydrolysis of an ester gives acid A and alcohol
B. The acid reduces Fehling’s solution. Oxidation
of alcohol B gives acid A. The ester is:
1) Mehthyl formate 2) Ethyl formate
2) Methyl acetate 4) Ethyl acetate 1) 2)
150. Which of the following products is formed
when adipic acid is heated?
3) 4)
1) 2) 155. The oxidation produces of 1-nitronaphthalene and
 -naphthylamine respectively are
1) phtalic acid and 3-aminophthalic acid
2) 3-nitrophtalic acid and phtalic acid
3) 4) 3) phtalic acid and phthalic acid
4) 3-nitrophtalic acid and 3-aminophthalic acid
NARAYANA SR AIEEE -MATERIAL 239 Carboxylic Acids

156. The organic product formed in the reaction.

162. i) C6 H 5COOH   C 
PCl
5 NH 3

 I  LiAIH 4
C6 H5COOH   [IIT-1995]
 II  H3O D 
P2O5
 C6 H 5CN 
H 2 / Ni
 E;
In the sequence of reaction ‘E’ is
1) C6 H5CH2OH
1) C6 H 5 NH 2 2) C6 H 5CONH 2
2) C6 H 5COOH & CH 4
3) C6 H 5CH 2 NH 2 4) C6 H 5COCl
3) C6 H 5CH 3 & CH 3OH 163. The product (D) of the reaction
4) C6 H 5CH 3 & CH 4 CH 3Cl 
KCN
  A  
H 2O / H



157. When propionic acid is treated with aqueous

 B  
NH
  C  
3 
D is
sodium bicarbonate, CO2 is liberated. the ‘C’ of
1) CH 3CH 2 NH 2 2) CH 3CN
CO2 comes from
1) methyl group 2) carboxylic acid group 3) HCONH 2 4) HC3CONH 2
3) methylene group 4) bicarbonate. 164. The correct product of the following sequence
158. Benzoyl chloride is prepared from benzoic acid of reactions
by
 CH 3 2 CHCOOH  4

i LiAH
Cl2 , hv SO2Cl2
1) 2)
ii H O  2
3) SOCl2 4) Cl2 , H 2O
PBr3 KCN H O, H 
159. An enantiomerically pure acid is treated with a  
DMSO
2
 
racemic mixture of an alcohol having one chiral
carbon. The ester formed will be.
1) Optically active mixture
1)  CH 3 2 CHCHBrCOOH
2) Pure enantiomer 2)  CH 3 2 CHCH 2COOH
3) Meso compound
4) Racemic mixture. 3)  CH 3  2 CHCH 2CH 2 NH 2
160. Write the structural formula of th main organic
product formed when: [IIT-1993] 4)  CH 3  2 C  CH COOH
C6 H 5COOH  CH 3 MgI  A  B 165. The final product of the following sequence of
B is the gas then B is. reactions

1) C6 H 6 2) C2 H 6
3) CH 4 4) C3 H 8

161. A
CH 3  CH 2  COOH Pand

bro min e
 
1.alcoholicKOH  excess 
 B in the
 
2. H 
sequence of reactions B is
1) 2)
1) CH 3CH 2COOH
2) CH 2  CH  COOH
3) CH 3COOH
4) CH 2  CH  CH 2  COOH
3) 4)
NARAYANA SR AIEEE -MATERIAL 240 Carboxylic Acids

166. Which of the following combination of reagents 170.

can brought transformation?


1) CH 3 O N a, Mg / ether , CO2 , H 2O / H 

2) CH 3 O N a, KCN / CMSO, H 2O / H 2 SO4 heat In the above sequence of reactions, ‘E’ is

3) Mg / ether , CO2 , H 2O / H  , , CH 3 O N a
4) NaOH , Mg / ether , CO2 H 2O / H  , CH 3 I
167. What is the missing reagent in the synthesis
1) 2)
shown below

3) 4)

LEVEL - V
MCQs WITH MORE THAN ONE
CORRECT ANSWERS
1) bromocyclopentane
171. Which of the following acids are dicarboxylic
2) 1,5 - dibromo pentane
3) 1,4 - dibromo butane acids
4) 1, 1 - dibromo cyclo pentane 1) Succinic acid 2) Glutaric acid
168. 3) Lactic acid 4) Cinnamic acid
172. Optical activity is expected for
1) 2 - methyl propanoic acid
2) 2 chloropropanoic aicd
3) methyl -2- methylproponoate
4) methyl - 2- chloropropnanoic acid
1) 5 - bromosalicylic acid and 5 - 173. Which of the following compounds will give
nitrosalicylic acid
ethyl alcohol on reduction with LiAIH4
2) O-bromophenol and O-nitro phenol
3) 2,4,6-tribromophenol, picric acid
4) 3, 5-dibromo salicylic acid and 3,5-dinitro
1)  CH 3CO 2 O 2) CH 3COCl
salicylic acid 3) CH 3CONH 2 4) CH 3COOC2 H 5
169.
174. Which of the following acids are unsaturated
one
1) Stearic acid 2) Acrylic acid
3) Oleic acid 4) Crotonic acid
175. Reaction of R  COOH with N 3 H gives
In the above sequence of reactons ‘D’ is RNH 2 as the main product. The intermedi
ates involved in this reacton are
1) RNHNH 2 2) RCON3
1) 2)
3) RNCO 4) RCONH 2
176. Acetic acid is obtained by the strong
3) 4) oxidation of
1) Ethyl acetate 2) Ethyl methyl ketone
3) Ethyl alcohol 4) Dimethyl ketone
NARAYANA SR AIEEE -MATERIAL 241 Carboxylic Acids

ASSERTION REASON TYPE QUESTIONS MATRIX TYPE MATCHING

177. Read the following statement and explanation and 180. Match the compounds of List-I with the distinction
answer as per the options given below [IIT-1994] reagents of List -II:
List - I List - II
Statement: Acetate ion is more basic than the (Compounds) (Reagents)
methoxide ion. a) HCOOH p) Effervescence of
Explanation: The acetate ion is resonance CO2 with NaHCO3
stabilized.
1) Both S and E are true but E is the correct
b) CH 3COOH q) Colour with FeCl3
explanation of S. c) Benzoic acid r) Decolourise Br2 water
2) Both S and E are true but E is not the correct d) Cinnamic acid s) Give silver mirror with
Tollens reagent
explanation of S. 181. Match the compounds of List - I with their
3) S is true but E is false. functional groups in List-II:
List - I List - II
4) S is false but E is true. a) Picric acid p) Do not contain car
178. Read the following statement and explanation and boxylic group
answer as per the options given below: [IIT-98] b) Ascorbic acid q) Phenolic group
c) Salicylic acid r) Carboxylic group
Assertion: Acetic acid does not undergo d) Formic acid s) Aldehydic group
haloform reaction. 182. Match the items of Column-A to these of Column-
Reason: Acetic acid has no alpha hydrogens. B
Column-A Column-B
1) If both assertion and reason are correct, and a) Red ants p) Dicarboxylic acid
reason is the correct explanation of the b) Oxalic acid q) Ethene on electrolysis
Asseration. c)Potassium r) Ethane with red P/HI
2) If both assertion and reason are correct, but succinate
reason is not the correct explanation of the d) CH 3  COOH s) Formic acid
assertion.
COMPREHENSION TYPE QUESTIONS
3) Asseration is correct but reason is in correct COMPREHENSION - 1
4) Assertion is incorrect but reason is correct. Dicarboxylic acids have two carboxylic groups,
e.g.
179. This question contains STATEMENT-I (Assertion)
and STATEMENT-2 (Reason) and has 4 choices
HOOC-COOH,- oxalic acid
(a), (b), (c) and (d) out of which ONLY ONE is HOOC-CH 2 -COOH,- Malonic acid
correct.
STATEMENT-I: p-Hydroxybenzoic acid has a
HOOC-(CH 2 )-COOH,- Succinic acid
lower boiling point than o-hydroxybenzoic acid. HOOC-(CH 2 )3 -COOH,- Glutaric acid
STATEMENT-2: o-Hydroxybenzoic acid has a
intramolecular hydrogen bond. HOOC-(CH 2 )4 -COOH,- Adipic acid
Acidity of dicarboxylic acid depends upon the
1) Statment-1 is True, Statement-2 is True; stabillity of intermediate ion and upon the distance
Statement-2 is a correct explanation for between two carboxylic groups. Shorter the
Statement-1 distance between two carboxylic groups, greater
2) Statment-I is True, Statement-2 is True; is the acidic character. Melting point of the acids
Statement-2 is a NOT correct explanation for depends on the symmetry. Greater the
Statement-1 symmetry, higher will be the melting point.
Dicarboxylic acids on heating give
3) Statement-1 is True, Statement-2 is False. monocarboxylic acid, alkanes, cyclic ketones
4) Statement-1 is Flase, Statement-2 is True. depending on the conditions.
NARAYANA SR AIEEE -MATERIAL 242 Carboxylic Acids
183. Which of the following is the most acidic?
CH3  COOH ( A) (B) 
(C)

Br2 / P NaCN HOH / H
1) Oxalic acid 2) Malonic acid 188.
3) Succinic acid 4) Adipic acid The product (C) will be :
184. Which of the following dicarboxylic acid is used
in the manufacture of nylon-6?
1) Succinic acid 2) Glutaric acid
3) Adipic aicd 4) Oxalic acid 1) 2)
185. Sodium adipate on electrolysis gives :
1) but-2-ene 2) but-1-ene
3) cyclobutane 4) cyclobutene

COMPREHENSION - 2
3) 4)
Carboxylic acids having at least one  - hydrogen
react with Cl2 or Br2 in the presence of LEVEL -I
phosphorus to give  - halo acids. The reaction
is known as Hell-Volhard-Zelinsky reaction (HVZ 1. 3 2.1 3. 3 4. 3 5. 2
reaction), 6. 2 7. 1 8. 1 9. 2 10. 2
11. 1 12. 2 13. 2 14. 1 15. 4
R  CH2  COOH 
P / Br2

 R  CH (Br)COOH 16. 4 17. 4 18 3 19 1 20. 1
The HVZ reaction is limited to the formation of 21. 2 22. 2 23. 2 24. 2 25. 1
26. 3 27. 4 28. 2 29. 4 30. 2
 - chloro and  - bromo acids and it is 31. 3 32. 4 33. 1 34. 1 35. 3
sometimes ackward to carry out. The reagents 36. 3 37. 2 38. 4 39. 4 40. 2
( X 2 and P) are noxious and the reaction time 41. 4 42. 4 43. 2 44. 1 45. 3
46. 2 47. 3 48. 3 49. 3 50. 4
is often long and the conditions of reaction are 51. 3 52. 2 53. 3 54. 1 55. 4
harsh . 56. 2 57. 4 58. 2 59. 4 60. 3
186. Which of the following carboxylic acids will not 61. 4 62. 1 63. 3 64. 2 65. 1
give HVZ reaction ? 66. 1 67. 1 68. 3 69. 1 70.2
71. 1 72. 2 73. 1 74. 1 75. 3
1) CH 3  COOH 76. 4 77. 3 78. 3 79. 3 80. 4
CH 3 81. 2 82. 3 83. 1 84. 1 85. 4
86. 2 87. 1 88. 3 89. 3 90. 1
|
2) 91. 1 92. 3 93. 2 94. 2 95. 2
CH 3  CH  COOH 96. 1 97. 3 98. 1 99. 3 100. 4
101. 1 102. 1 103. 1 104. 2 105. 4
3) CH 3  CH 2  COOH 106. 1 107. 2 108. 2 109. 3 110. 1
111. 4 112. 2 113. 3 114. 1 115 2
CH 3 116. 3 117.4 118. 3 119. 2 120. 4
| 121. 4 122. 4 123. 4 124. 3 125. 3
CH 3  C  COOH 126. 2 127. 3 128. 3 129. 2 130. 2
4) | 131. 3 132. 3 133.2 134. 2 135.3
CH 3 136. 4 137.3 138.3 139. 3 140. 2
187. Whic of the following will be obtained when acetic 141. 2 142. 3 143. 2 144. 1 145. 3
acid is subjected to HVZ reaction ? 146. 3 147. 1 148. 3 149. 1 150. 2
151. 4 152. 2 153. 4 154. 4 155. 2
B r 156.1 157.4 158.3 159.1 160.3
| 161.2 162.3 163.4 164.2 165.2
B r  C  C O O H 166.1 167.3 168.3 169.2 170.1
1) BrCH 2COOH 2) | 171. 1,2 172. 2,4 173. 1,2
H 174. 2,3,4 175. 2,3 176. 2,3,4
177. 4 178. 3 179. 4
Br 180. (a-p,s ), (b-p,q),(c- p,q), (d-p,r)
| 181. (a-p,q ), (b-p),(c- q,r), (d-r,s)
Br  C  COOH 182. (a-s ), (b-p,r), (c- q), (d-r)
3) 4) All of these 183. 1 184. 3 185. 3 186.4 187. 4
|
Br
188. 1
NARAYANA SR AIEEE -MATERIAL 243 Carboxylic Acids

HINTS AND SOLUTIONS 19 Electron-releasing group weakens the acidic

nature of COOH
1. HCOOH is not a derivative of CH 3COOH
2. Formicus means red acts C2 H 5OH 
PCC or
 CH 3CHO
20. PDC

 CH 3 CN 
Hydrolysis
21. CH3Cl+KCN H   or OH 
( A)

3. OH O
| ||
CH 3  C  NH   CH 3  C  NH 2 
H O
 CH 3 COOH  NH 3
2

(B)

4. Cn H 2 n1COOH or Cn H 2nOn
22. CH3OH+CO     
Cobalt ( or )
Rhodium high pressure
 CH3COOH

5. 2-phenyl ethanoic acid. 23.

Benzamide Benzoic acid

6. C 2 H 5 CO 2 H, & CH 3CO 2 CH 3 are a pair of
functional isomers 24. C O 2
+ C H 3
- M g - B r 

7. Cn H 2 n1COOH or Cn H 2nOn O
||
C H  C  O  M gB r 
3
X   H
3O


CH 3COOH +Mg(Br)OH
8. (Y)

 CH3 CN 
Hydrolysis
25. CH3Cl+KCN H   or OH 

9. and -OH OH O
| ||

10. methyl ethanoate

CH 3  C  NH   CH 3  C  NH 2 
H O
 CH 3 COOH  NH 3
2

C2H5OH   CH3COOH

air
26. MicodermaAceti
11. -COOH- oic acid Ethyl alcohol Acetic Acid
27. Esters on hyrolysis give alcohol and
12. ethanoic acid.
carboxylic acid
13. Ethyal ethanoate
14. Propionic acid. 28. 6 - 10% acetic acid

15.  CH 3 3 COOH is weakest acid.

29.
16. Due to  I . effect of CH 3 groups
17. Due to  I .effect of 3Cl atoms
18. Follow applications of inductive effect. The Ethyl benzoate Benzoic acid
negative charge on carboxylate ion is 30. The high Boiling point of acetic acid in
dispersed more due to - I.E. of F atom comparision to alkanes, alkyl halides or
alcohols of nearly same molecular masses is
due to more strong hydrogen bonds between
. The carboxylate acetic acid molecules.

ion thus becomes more stable and acid more

reactive
NARAYANA SR AIEEE -MATERIAL 244 Carboxylic Acids

LiAlH 4
31. C2 H 5OH 
H3O

+
 CH 3COOC2 H 5  H 2O
50. CH3COOH   C2H5OH
Catalyst
O O
Ethyl acetate 51.
P O5
2CH3COOH  2 
||
 CH  C O  C CH  H O
||

3 3 2
32. CH 3COOH  PCl5  CH 3COCl  POCl3  HCl
Acetic Anhydride
52. C H 3 C O O N a  N a O H     C H 4  N a 2 C O 3
C aO
S o d a lim e 
33. CH 3 COONa  NaOH    CH 4  Na 2 CO 3
CaO
Soda lim e 
53. Sodalime is decarboxylating reagent
LiAlH 4
34. CH3COOH   C2H5OH 54. CH3COOH LiAlH 4
 C2H5OH
35. CH3COOH LiAlH 4
  C2H5OH 55. CH 3COOH  S 2Cl2  no reaction.
36. NaHCO3  CH3COOH  CH3COONa  CO2  H 2O 56. Carboxylic acids dissolve in aq. NaOH due to
Deprotonation.
37. CH3COOH + 2Na  2CH3COONa + H2

57. C2 H5OH 

H2 SO4

Catalyst
CH3COOC2 H5  H2O
38.
58. In H.V.Z reaction reagent is halogen and red
phosphorus.
39.
NaHCO3  CH3COOH  CH3COONa  CO2  H 2O 59. CH 3COOH  PCl5  CH 3COCl  POCl3  HCl
40. CH3COOH + 2Na  2CH3COONa + H2 60. Picric acid is 2,4,6- trinitrophenol
61 COOH is electron -attracting group. It is
+
41. C2 H 5OH 
H3O

Catalyst
 CH 3COOC2 H 5  H 2O
thus meta director.
Ethyl acetate 62. Valeric acid contain 5 carbon atoms
42. CH3COOH  PCl5  CH3COCl  POCl3  HCl 63. Acetic acid is less acidic than mineral acids.
64. (IV) CF 3 COOH > (III) Cl 2CHCOOH >(I)
HCOOH > (II) CH3COOH
43. 1
65. Acidic strength 
.
P ka
44. CH3COOH 
Re dP
Cl2
 CH2ClCOOH 66. (I) methanoic acid > (II) ethanoic acid > (III)
Monochloro acetic acid propanoic acid > (IV) butanoic acid
67. CHCl2COOH > CH2ClCOOH > CH3COOH
CH2ClCOOH 
 CH2Cl2COOH
Re dP
Cl2
di-chloro acetic acid
68.
CH2Cl2COOH 
 Cl3COOH
Re dP
Cl2
tri-chloro acetic acid 69 The larger the electronegativity of halogen, the
in the above reaction  -hydrogen are replaced larger the acidity of substituted acetic acid.
by chlorines 70 Electron-attracting group makes benzoic acid
more strong acidic and elctron-releasing group
45. CH 3COOH  PCl5  CH 3COCl  POCl3  HCl makes it less acidic. the pKa follows the
46. C H 3 C O O H  N H 3  C H 3 C O O N H 4  
(X )
 C H 3 C O N H 2  H 2O
(Y )
reverseorder.

 CH3 CN 
Hydrolysis
71. CH3Cl+KCN H   or OH 
47.
CH3COOH  3Cl2 
Red 'P'
 Cl3C COOH  3HCl OH O
| ||
48. CH 3 COONa  NaOH    CH 4  Na 2 CO 3
CaO
Soda lim e 
CH 3  C  NH   CH 3  C  NH 2 
H O
2
 CH 3 COOH  NH 3

49. a)(CH3COO)2 Ca   1 air  CH COOH
Calcium acetate 72. CH3CHO + O 
Mn+2
CH3COOH
2 2
O
|| Acctaldehyde Acetic Acid
CH 3  C  CH 3  CaCO3
NARAYANA SR AIEEE -MATERIAL 245 Carboxylic Acids
87. (CH 3 ) 2 CHCOOH < CH 3 CH 2 COOH <
73. C O 2
+ C H 3
- M g - B r 
 ClCH2CH2COOH < CH3COOH < ClCH2COOH
O 88.
|| +
CH 3 COOH + C 2 H 5OH    CH 3COOC 2 H 5  H 2 O
 H O
 C  O  M g B r  
3 H O 3
CH Catalyst
3
Ethyl acetate
CH 3COOH +Mg(Br)OH
CH 3Cl  KCN 
 KCl
 CH 3CN 
H 2O

74. CH 3CN  CH 3COOH 89.
CH 3COOH 
P2O5
  CH 3CO  2 O
75.
1
90. CH 3COOH  Na CH 3COONa  H2
2
) a
1 mole 1 mole 1/2 mole
60g 23g 11.2 lit
Tolune Benzoic acid 0.1 mole 0.1 mole = ?
= 6g 2.3 g 1.12 lit.
91. CH3COOH  NaHCO3  CH3COONa  H2O  CO2 
76.
HCOOCH 3  NaHCO3  no reaction.
77. 6 - 10% acetic acid
92. C2 H 5Cl 
AqKOH
C2 H 5OH
78. C O 2
+ C H 3
- M g - B r 

C 2 H 5OH  CH 3COOH  CH 3COOC2 H 5  H 2O
O
||
CH  C  O  M g B r  
3
 H O

RCOOH 
NH 3
 RCOONH 4 
heat
 H 2O

3
93.
RCONH 2 
P2O5
 RCN
CH 3COOH +Mg(Br)OH  H 2O

79. CH 3 COO C2 H 5  H 2O  CH 3COOH  C2 H 5OH 94. CH 3COOH 

LiAlH 4
 C2 H 5OH 
Ni
H2
 C2 H 6
(X )

80. CH3COOH LiAlH 4

  C2H5OH 95. CH 3COOH 
LiAlH 4
 C2 H 5OH
81. Same as Q. 45 
H 2 SO4
 CH 2  CH 2 
S 2 Cl2
  Cl  CH 2CH 2  S
1700 C
mustard gas
or war gas
82. does not contain - 96. Due to chetation by hydrogen bond
2 

hydrogen atom.
C2 H 2  H 2O 
Hg / H
 CH 3CHO 
(O )

97.
83 The increasing number of R groups makes CH 3COOH 
PCl3
 CH 3COCl
the esterification more difficult.
84 Methanoic acid (i.e. formic acid) reduces am 98. Due to decrease in p.ka value
moniacal solution (Tollens reagent) while
ethanoic acid does not. 99. CH 3CHO 
( O ) KMnO4 orK 2 Cr2O7
H 2 SO4
 CH 3COOH
85 CO2 comes from HCO3 
100. CH 3CHO  Na  no reaction.
O
|| +

86.O=C=O+ CH3 Mg Br 

 CH 101.CH 3 COOH +C 2 H 5OH H O
  CH 3COOC 2 H 5  H 2 O
3

 C  O  M gBr Catalyst
3
Ethyl acetate
O
||
C2 H 5Cl  KCN   C2 H 5CN 
H 2O

CH
3  C  O  M gBr 102.
 KCl

C2 H 5COOH
 CH 3COOH +Mg(Br)OH


 H
3O

Acetic acid =  C3 H 6O2 

NARAYANA SR AIEEE -MATERIAL 246 Carboxylic Acids

  O
103. CH 3CHO  CH 3COOH
1
104 CH 3COOH  Na CH 3COONa  H2
2
CH 3COONa  NaOH 
CaO
 CH 4 119.
105. Cleavage of O- H bond takes place

106. HCOOH can reduces ammonical

AgNO3
120.  -keto acids are readily decarboxylated.
121.
C H 3 C O O H  alcohol gives ester
CH3CN CH3COOH CH3COONH4
H2O NH3

X  HCOOH , Y  CH 3COOH


CH3CONH2  H2O
107. Cleavage of O  H bond takes place
108. Cleavage of O  H bond takes place
109. Amines of are not the derivatives of carboxylic 122. CH 3COOH 
3
 CH 3COO 2 Ca
CaCO

acids

 CH 3COO 2 Ca 

110. C H 3 C O O C 2 H 5  H
3O

 C H 3C O O H  C 2 H 5O H 
 CH 3COCH 3  CaCO3
2CH 3COOK  2 H 2O kolbe
electrolysis
 123. RCOOAg  R ' X  RCOOR ' (ester); this
CH 3  CH 3  2CO2  2 KOH  H 2 is called Hunsdiecker reaction.
124.
 CH COO2 Ca
CaCO
CH3COOH 
3
3

CH 3COOH  NH 3  CH 3COONH 4  
111. Heat
 CH3COCH3 CH 3CONH 2 
P2O5
 CH 3CN
112. Product is CH 3  CH 3 or C2 H 6 CH 3CN is ethane nitrile or acetonitrile or

24 methyl cyanide
% of C in C2 H 6   100  80%
30 CH 3CH 2COOH 
Cl2
 CH 3CHCl .COOH
125.
113
Soda  lim e
R  COOH 
 CO2
RH 
KOH alc
 HCl
 CH 2  CH .COOH
  O
114. CH3COCH3  CH3COOH  HCOOH
126.
115. CH 3COOH 
AlPO4
 CH 2  CO  H 2O
127. RCOOH  CH 2 N 2  RCOOCH 3  N 2 ;
116. CH 3CH 2 COOH 
Cl
 CH 3CH  Cl  COOH .
P4

2 methyl esters are formed

This is Hell-Volhard-Zelinsky reaction.
128. CH 3 Br  Mg 
Ether
 CH 3 MgBr 
HCHO

117. RCOOH  N 3 H  RNH 2  CO2  N 2
  O
H 3C  CH 2  OMgBr 
HOH
 H 3C  CH 2  OH
118. CH 3CHO  CH 3COOH
129.
CH 3CHClCOOH 
KOHalc
CH 2  CHCOOH

130. CH 3COOH  N 3 H  CH 3 NH 2  N 2  CO2

NARAYANA SR AIEEE -MATERIAL 247 Carboxylic Acids

131. Y is CH 3CN ; Z is CH 3COOH

140.
132 Jones reagent is CrO3  H 2 SO4

133

1 3 4

141.
135.

136. Aldehydes are oxidised by strong and mild

oxidising agents to carboxylic acids
137.

142. CH 3CH 2 COOH Cl

red P
 CH 3CHClCOOH
2

138.

alc . KOH
 HCL
 CH 2  CHCOOH
Acrylic acid

143. Aldehydic group gets oxidised to carboxylic

group. Double bond breaks and carbon gets
oxidised to carboxylic group.
144. LiAlH 4 can reduce COOH group and not the
double bond.
CH 2  CH  COOH  CH
LiAIH 4

2
 CH  CH 2 OH

145. pK a   log K a ; HCOOH is the strongest

acid and hence it has the highest K a or lowest
pK a value
139.

146.
NARAYANA SR AIEEE -MATERIAL 248 Carboxylic Acids
152. This is Hoffmann bromamide reaction callied
CH 3
CH 3 out by Br2  NaOH
153.
HOH

CH  OH  CN
CH  OH  COOH

OH OH

154.

147. The correct order of increasing acid

strength 155. Nitro bearing benzene ring is resistant to
oxidation and amino bearing benzene is more
CF3COOH  MeOCH 2COOH  CH 3COOH
susceptible oxidation. the products are 3-
nitrophthalic acid and phthalic acidic.
( Me)2 CH .COOH Electron withdrawing 156. C6 H 5COOH 
4
 C6 H 5CH 2OH
LiAlH

groups increase the acid strength and

157. NaHCO3 is comparitively less stable . Hence
electron donating groups decrease the acid
strength. CO2 liberates from HCO3
148. 158.
C6 H 5COOH  SOCl2  C6 H 5COCl  SO2  HCl
CH 3CH  OH  COOH  
Fenton ' s reagent
O  
159. The optically active acid will react with d and l
CH 3COCOOH forms of alcohol present in the racemic mixture
 Pyruvic acid  at different rates to form two diasteromers in
149. HCOOH is reducing agent unequal amounts leading to optical activity of the
product.
160.
C6 H 5COOH  CH 3 MgI  C6 H 5COOMgI  CH 4
 A  B
150. 161.
CH 3CH 2COOH 
P and Br2
HVZ reaction
 CH 3CH  Br  COOH
( A)

 
( i ) Alc . KOH ( excess )
( ii ) H 
 CH 2  CHCOOH
( B)
151. CH 3COOH  PCl5  CH 3COCl 
C6 H 6
Anhy . AlCl3

C6 H 5COCH 3 
C2 H 5 MgBr
 C6 H 5  C  OH  C2 H 5   CH 3
NARAYANA SR AIEEE -MATERIAL 249 Carboxylic Acids

162. 167.
C6 H 5COOH 
PCl5
 C6 H 5COCl 
NH 3

C 
C6 H 5CONH 2 
P2 O5
 C6 H 5CN 
H 2 / Ni
 C6 H 5CH 2 NH 2
 D E
163:

168: During nitration and brominaton of Salicylic

164: acid -COOH group is eliminated
169:
COOH 
LiAIH 4
H 2O
 CH 2OH 
PBr3


CH 2 Br 
KCN
DMSO
 CH 2CN 
H
H 2O
 CH 2COOH
165:

170.

166.

171. 1) Succinic acid HOOC  CH 2 2 COOH

2) Glutaric aicd - HOOC  CH 2 3 COOH
*
172. 2) H 3C  C H  Cl  COOH 2- Chloroproponoic
acid
*
4) H 3C  C H  CH 3  COOCH 3 methyl - 2 -
methyl proponoate
173. 1)  CH 3CO 2 O 
LiAlH
 2CH 3CH 2OH
4

2) CH 3COCl   CH 3CH 2 OH

4 LiAlH
NARAYANA SR AIEEE -MATERIAL 250 Carboxylic Acids

174. 2) Acrylic acid - CH 2  CH  COOH

3) Oleic acid
- CH 3  CH 2 7 CH  CH  CH 2 7 COOH

4) Crotonic aicd - CH 3CH  CHCOOH

175 RCOOH  N 3 H 
 RCON 3  H 2O
RCON 3 
 R  N  C  O  N2

176. 2) CH 3COCH 2CH3 

K2Cr2O7
H 2 SO4
 2CH 3COOH

i KMnO ,OH ,

3) CH3CH2OH  CH3CHO  CH3COOH

K Cr O
2 2 7 4
H SO
2 4 ii H


4) CH 3COCH 3 
K 2Cr2O7
H 2 SO4
 CH 3COOH

177. Statement is in correct

in CH 3COOH and CH 3OH , CH 3COOH
is strong and CH 3OH weaker. Therefore
CH 3COO  ( Acetation ) is weaker conjugate
base and CH 3O  ( methoxide ion ) is strong
conjugate base.

178. Assertion is correct carbonylcompounds having

 - hydrogen undergo haloform reaction.
Reason is incorrect. Acetic acid gas three -
hydrogens.

179. Para Hydroxybenzoic acid forms inter molecular

hydrogen bond with water where as Ortho
hydroxybenzoic acids forms intramolecular
hydrogen bonds. Hence, boiling point of Para
Hydroxybenzoic acid is more

* * *