CARBOXYLIC ACIDS

Contents
Topic Page No.

Theory 01 - 08

Exercise - 1 09 - 13

Exercise - 2 13 - 17

Exercise - 3 17 - 19

Exercise - 4 20 - 23

Exercise - 5 23 - 24

Answer Key 25 - 25

Syllabus
Carboxylic acids, Methods of preparation, physical properties, chemical
properties & formic acid

Name : ____________________________ Contact No. __________________

 CARBOXYLIC ACIDS
INTRODUCTION

(a) Organic compounds in which – COOH group is present are called as ‘Carboxylic Acid’.
(b) These compounds are also called fatty acids because their higher members like Palmitic acid or
stearic acid were usually obtained from animal fats.
(c) The term ‘Carboxylic’ was firstly proposed by scientist ‘Bayer’.
(d) Their general formula is
CnH2nO2 or CnH2n+1–COOH
(e) Hybridisation state of carboxylic carbon is sp2.
(f) In carboxylic acids, both oxygen-carbon bond lengths are equal due to resonance. It is 1.28 Aº.
(g) On the basis of number of –COOH group, they are called mono, di or tri carboxylic acid.
(h) Acids shows chain and functional isomerism. They shows functional isomerism with ester.
eg.

(functional isomers)

(chain isomers)
&

METHODS OF PREPARATION
From Alcohol :
(a) By oxidation :
[ O]
R – CH2 – OH   R – CHO [
O]
 R – COOH
H2 O

Acidic KMnO4 or K2Cr2O 7 may be used in the above reaction.

(b) By reaction with CO : –

 BF3
R –O – H+  CO  
200300ºC
200 atm.

From Aldehyde and Ketone :

4 acidicKMnO
R – CHO + [O]  
or   R – COOH
K 2Cr2 O7

From Alkyl Cyanide : Cyanides gives acid on complete hydrolysis.

H O
R – C  N   3
 R – COOH
From Trihaloalkane : 1,1,1- Trihaloalkane reacts with aq. KOH and forms respective acid.

  
H O

2

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A-479 Indra vihar, kota Carboxylic Acids_Advanced # 1
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 From Acid derivative (By hydrolysis) :




R – O – C – R + H – O – H

R – C – NH2 + H – OH 

From Dicarboxylic Acid (Decarboxylation) :

glycerol  H3BO 3
   HCOOH
 CO 2 (110 º C )

NOTE : The above reaction is lab method to prepare formic acid.

COOH

 CH2
CO 2 H
ethanoic acid
From Grignard Reagent :

From Carbonylation of sodium alkoxide :

High temp.
Sodium alkoxide+CO  

Pr essure

RCOONa H
3O
 NaCl + RCOOH

From Alkenes : (CO,H2O)

RCH = CH2 + CO + H2O H

3PO4 
/

highpressure

R — CH — CH3
|
COOH
From Arndt-Eistert Process :
This reaction is used in ascendig series. In this reaction alkanoyl halide reacts with diazomethane and
acid is obtained on hydrolysis.

Ag O 
HCl
CH3COCl+CH2N2   CH3COCHN2 2 CH3 – CH = C =O H
3O

N2

CH3 – CH2 – COOH

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 Manufacture of formic acid only :

210 o
(a) NaOH+CO   HCOONa
6 10 atom.

HCOONa H
2 SO
4  HCOOH

high
(b) CO + H2O   HCOOH
pressure /BF3

200º
(c) CH3OH+CO   HCOOCH3
high pressure

 dil
.H2 S
O4
  HCOOH + CH3OH

METHODS OF PREPARATION OF CARBOXYLIC ACID

Ex.1 Which of the following products is formed when adipic acid is heated -

CH2 – CH2
(A) (B) C=O
CH2 – CH2

CH2 – CH2CO
(C) O (D)
CH2 – CH2CO

(Ans.B)

300ºC
Sol. HOOC(CH2)4COOH   


cyclo pentanone

Ex.2 Malonic acid and succinic acid are distinguished by -

(A) Heating (B) NaHCO3 (C) Both A & B (D) None of these
(Ans.A)


CH2CO
Sol.  O
CH2CO
succinic anhydride


 CH3COOH + CO2

two – COOH group on one carbon atom gives CO2 on heating.

two – COOH group an adjacent carbon atoms lose H2O to give an hydride on heating.


 CO 2 + H2O + CO,

CH2 – COOH
COOH 

 CH3COOH + CO2, 

CH2
COOH CH2 – COOH
Physical & Inorganic By Organic Chemistry By
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Ex.3 Hydrolysis of 1,1, 1-trichloro derivative (A) of alkane gives a molecule (B) on alkaline hydrolysis which
produces red coloration with aqueous FeCl3. The compound (A) is -
(A) CH3CH2CCl3 (B) CH3CCl3 (C) CHCl3 (D) None
(Ans.B)
Sol. CH3CCl3 KOH
 CH3COOH Fecl
 3 ( aq.)
 (CH3COO)3 Fe (Red)

Ex.4 Which of the following is the best representation of the structure of the carboxylate ion -

– 
O O
(A) (B) R – C (C) R – C (D) None of these
O O
– 

(Ans.B)
Sol. Both C – O bonds are identical and each O possesses partial negative charge.

PHYSICAL PROPERT IES

(a) Carboxylic acids are colourless with specific smell liquid. They are in liquid state upto 9 carbon
and above 9 carbon they are solids.

(b) Lower carboxylic acids are soluble in water. It is due to H–bonding. Higher carboxylic acids are
insoluble in water due to increase in covalent character.

(c) Their melting point and boiling point  molecular mass.

1

No. of branches
(d) Boiling point of acids are comparatively higher than equivalent esters due to H – bonding. For
example, methyl formate (HCOOCH3) has a boiling point 57ºC whereas acetic acid has a boiling
point 118ºC.

(e) Formic acid is used in leather industries, also known as corrosive.

(f) 8 – 10% acetic acid is called ‘Vinegar’.

(g) At 16–20ºC pure acetic acid converts into ice like solid called glacial acetic acid.

(h) In industries, acetic acid is prepared by oxidation of ethanol and oxidation occurs by aceto bacter
aceti or micoderma aceti bacterias. The process is called quick vinegar process.

(i) Boiling point of formic acid is 100.5ºC while acetic acid has 118ºC. For removal of water from formic
acid we can use reagent PbCO3 (lead carbonate) and H2S.

(j) Acidic strength of an acid can be increased by the addition of – I groups in place of -hydrogen
atoms. Acidic strength can be decreased by addition of +  groups.
::
::

Cl  CH2  C – H CH3  C – H

O O
more acidic less acidic

Physical & Inorganic By Organic Chemistry By

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CHEMICAL PROPERT IES
Chemical reaction of carboxylic acids are classified in five categories.
Reaction of Hydrogen Atom of Carboxylic Acid.
Reaction of – OH group of Carboxylic Acid.
Reaction of group of Carboxylic Acid

Reaction of – COOH group of Carboxylic Acid.

Reaction of Alkyl group of Carboxylic Acid.

Reaction of Hydrogen Atom of Carboxylic Acid

(a) Carboxylic acid reacts with base and forms salt, thus showing acidic character.

(a) 

(b) R – C – O – H + H – O – K  R – C – OK
O O
Pottasium alkanoate

(c) R – C – O – H + H – O – Ag R – C – OAg

O O
Sliver alkanoate

O O
R–C–O–H H–O R–C–O
(d) + Ca Ca
R–C–O–H H–O R–C–O
O O
Calcium alkanoate

(e) 

O
 ||
 R – C – NH2 + H2O

Ammonium alkanoate

Reaction of – OH group of Carboxylic Acid :

(a) Reaction with PCl5 or PCl3 or SOCl 2 :

R – C – O – H + PCl5 
O



 R – C – Cl + SO2 + HCl

O
Alkanoyl chloride

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 PO
2 5
(b) Dehydration : 
H2O

conc. H SO
2 4
(c) Reaction with Alcohol :   
H2O

conc. H SO
2 4
  
H2O

Reaction of – C – group of Carboxylic Acid :

||
O
LiAlH4
(a) Reduction :    R – CH2OH

NOTE : In the above reaction group converts into – CH2 – group.

Reaction of – COOH group of Carboxylic Acid

For this reaction initially we form salt of carboxylic acid with base.
(a) Alkane Preparation :

R–C–O–H + H – O – Na 
O
  

NaOH CaO
 

R – C – OK   R – R
Kolbe's reaction
alkane
O

(b) Alkyl Halide Preparation : –

AgOH Br / CCl
  2
 4
 

(c) Carbonyl Compound Preparation (Pyrolysis of calcium salts) :


Ca
  dry distillation
  


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 (d) Alkyl Cyanide Preparation :

O O O
|| ..
NH3
||   ||
 P2 O 5 ,
R  C  OH   R  C  ONH4   R  C  NH2    R – C  N

(e) Schimdt Reaction :

O 
O
|| ..  || .. 
N2
R  C  OH+ :NH  N  N ——— R  C  NH  N  N  
 ——— O = C  N  R
.. | H O
 3
B
RNH2
Reaction of Alkyl group of Carboxylic Acid
(a) Hell – Volhard – Zelinsky Reaction : –

Re d P
 


NOTE : Formic acid does not show the above reaction due to absence of alkyl group.

SPECIAL FEATURES OF FORMIC ACID

(a) Formic acid shows acidic character due to the presence of – COOH group as well as shows
reducing character due to the presence of – CHO group.

(b) It reduces Tollen’s reagent and forms silver mirror.

(c) It reduces mercuric chloride and forms black ppt. of mercury.
(d) It decolourises the pink colour of acidic KMnO4.
(e) It forms brown ppt. of MnO2 with basic KMnO4.
(f) It converts the orange colour of acidic K2Cr2O 7 into green colour.
(g) It reduces Fehling solution but benzaldehyde cannot reduce Fehling solution.

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DISTINCTION BETWEEN FORMIC ACID AND ACETIC ACID

S.
No. HCOOH CH3COOH
1 Decomposes on heating to Stable
give carbon dioxide and
hydrogen.
2 With concentrated sulphuric Stable
acid gives carbon monoxide
and water
3 With halogens, there is no Substituted acids
action are formed
4 Reduces ammoniacal silver No action
nitrate and Fehling's
5 Calcium salt on heating Calcium salt on
gives formaldehyde. heating gives
6 Sodium salt on heating gives No action
sodium oxalate + hydrogen
7 Sodium salt + soda lime Methane is produced
gives hydrogen on heating
8 Electrolysis of alkali salt Ethane is obtained
solution gives hydrogen
9 Decolourises acidified No action
KMnO4 Solution
10 Dichromate soln. Turns into No action
green coloured solution

Chemical Reactions

Ex. 5 Reaction of CH3 COOH with CH3CH2 MgBr yields :

(A) An alkene (B) An ester (C) An alkane (D) A tertiary alcohol
(Ans. C)
Sol. Grignard reagents with compounds containing active hydrogen atom form alkanes corresponding to the
alkyl group of the Grignard reagent.

CH3 COOH+CH3CH2MgBr 

alc.
Ex. 6 CH3CH2COOH  Cl
 2 /Fe
 X  
 Y Compound Y is :
KOH

(A) CH3CH2OH (B) CH3CH2CN (C) CH2=CHCOOH (D) CH3CHCICOOH

(Ans.C)
alc.
Sol. CH3CH2COOH  Cl
 2 /Fe
 

KOH

Ex. 7 Benzoyl chloride is prepared from benzoic acid by :

(A) Cl2, h (B) SO2Cl 2 (C) SOCl2 (D) Cl2, H2O
(Ans.C)
Sol. C6H5COOH+SOCl2  C6H5COCl+SO2+ HCl

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 OBJECTIVE QUESTIONS

PREPARATION & TARGET COURSE

1. Which of the following products is formed when adipic acid is heated -

CH2 – CH2
(A) (B) C=O
CH2 – CH2

CH2 – CH2CO
(C) O (D)
CH2 – CH2CO

2. Malonic acid and succinic acid are distinguished by -

(A) Heating (B) NaHCO3 (C) Both A & B (D) None of these

3. Hydrolysis of 1,1, 1-trichloro derivative (A) of alkane gives a molecule (B) on alkaline hydrolysis which
produces red coloration with aqueous FeCl3. The compound (A) is -
(A) CH3CH2CCl3 (B) CH3CCl3 (C) CHCl3 (D) None

4. Which of the following is the best representation of the structure of the carboxylate ion -

– 
O O
(A) (B) R – C (C) R – C (D) None of these
O O
– 

5. Which of the following compounds does not have a carboxyl group :

(A) Methanoic acid (B) Ethanoic acid (C) Picric acid (D) Benzoic acid

6. 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 -
(A) Methyl formate (B) Ethyl formate (C) Methyl acetate (D) Ethyl acetate

7. Which one of the following on oxidation will not give a carboxylic acid with the same number of carbon
atoms -
(A) CH3COCH3 (B) CCl3.CH2CHO (C) CH3CH2CH2OH (D) CH3CH2CHO

8. Identify Z in the sequence

(i) heat 
CH3COONH4    Y H
2O (H )
Z -
( ii) P2 O 5

(A) CH3CH2CONH2 (B) CH3CN (C) CH3COOH (D) (CH3CO)2O

9. When oxalic acid is heated, which one of the following is formed along with CO2 -
(A) Acetic acid (B) Glyceric acid (C) Formic acid (D) None of these

10. Which one of the following reacts with Grignard reagent to form an addition product which can be
hydrolysed to a carboxylic acid?
(A) O2 (B) CO 2 (C) SO 2 (D) None

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11. A halogen compound ‘A’ on hydrolysis with dilute alkali followed by acidification gives acetic acid. The
compound X is -
(A) ClCH2CH2Cl (B) CH3CHCl2 (C) ClCH2CHCl2 (D) CH3CCl3

12. Acetic acid is obtained when -

(A) Methyl alcohol is oxidised with potassium permangnate
(B) Formaldehyde is oxidised with potassium dichloromate and sulphuric acid
(C) Acetonitrile is hydrolysed with a dilute mineral acid
(D) Glycerol is heated with sulphuric acid

13. In Quick Vinegar Process, the aerial oxidation of ethyl alcohol to acetic acid is brought about by -
(A) Acetic (B) Maltase (C) Invertase (D) Mycoderma aceti

14. Sodium salt of formic acid on strong heating followed by acidification gives-
(A) Formic acid (B) Oxalic acid (C) Formaldehyde (D) Acetaldehyde

15. When malonic acid is heated, it gives -

(A) Formic acid (B) Oxalic acid (C) Acetic anhydride (D) Acetic acid

PHYSICAL PROPERTIES

16. The acid D obtained through the following sequence of reactions is -

Alc.KOH 3 Br KCN H O
  A
C2H5Br 2
CCl
B  C  
4 (excess)

(A) Succinic acid (B) Malonic acid (C) Maleic acid (D) Oxalic acid

17. In the following reactions -

(i) CH3CH2ONa CO,

 Δ
 A
under pressure

H3PO 4
(ii) CH2 = CH2 + CO + H2O   B

under pressure

A and B respectively are :

(A) CH3CH2COOH in both cases (B) CH3CH2CHO in both cases
(C) CH3CH2COOH, CH3CHO (D) CH3CHO, CH3COOH

18. Acetic acid exists as dimer in C6H6 due to-

(A) Condensation reaction (B) Hydrogen bonding
(C) Presence of a carboxyl group (D) Presence of hydrogen at -carbon

19. Carboxylic acid group can be detected by -

(A) Sodium bisulphite test (B) Fehling’s solution test
(C) Tollen’s reagent (D) With NaHCO3

20. The pKa values of the four carboxylic acids are given below. Which of the following is the weakest acid?
(A) 4.38 (B) 2.87 (C) 1.26 (D) 0.64

21. Phenol is a weaker acid than acetic acid because -

(A) Phenoxide ion is better stabilized by resonance than acetate ion
(B) Acetate ion is better stabilized by resonance than phenoxide ion
(C) Phenol is less soluble in water than acetic acid
(D) Both phenoxide ion and acetate ion are equally stable

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22. Which of the following is the weakest acid ?
(A) Cl3CCOOH (B) Cl2CHCOOH (C) ClCH2COOH (D) CH3COOH

23. Formic acid is a stronger acid than acetic acid. This is due to the fact that ?
(A) Formic acid is a reducing agent
(B) Formic acid molecule is of smaller size
(C) There is no alkyl group on -carbon in formic acid
(D) Formic acid does not undergo association

24. Which of the following dicarboxylic acids contains the most acidic hydrogen ?
(A) Maleic acid (B) Fumaric acid (C) Succinic acid (D) Malonic acid

25. Increasing pKa of o, m- and p-nitrobenzoic acid is ?

(A) p < m < o (B) o < m < p (C) o < p < m (D) m < p < o

CHEMICAL PROPERTIES

26. Amongst the acids,

(i) CH  CCOOH (ii) CH2 = CHCOOH and
(iii) CH3CH2COOH, the acid strength follows the sequence
(A) (i) < (ii) > (iii) (B) (i) > (ii) > (iii) (C) (i) = (ii) = (iii) (D) (i) = (ii) > (iii)

27. The increasing order of acidity of  and -chlorobutyric acids is -

(A)  <  <  (B)  <  <  (C)  <  <  (D)  <  < 

28. Which of the following is a polyprotic acid -

(A) Acetic acid (B) Benzoic acid (C) Salicylic acid (D) Oxalic acid

29. Which of the following acids combines the properties of an aldehyde and an acid ?
(A) Benzoic acid (B) Acetic acid (C) Formic acid (D) Oxalic acid

30. Formic acid reacts with PCl5 to form -

(A) Acetyl chloride (B) Methyl chloride
(C) Carbon monoxide and hydrogen chloride (D) formyl chloride

31. The Hell-Volhard Zelinsky reaction is used for preparing a/an -

(A) -Haloacid (B) -Haloacid (C) Acid halide (D) -Haloacid

32. When excess of chlorine is passed through acetic acid in presence of red phosphorus, it forms -
(A) Acetyl chloride (B) Chloral
(C) Trichloroacetic acid (D) Methyl chloride

Mg Dry
33.  Y Cl
Identify Z in the following reaction sequence CH3I  X  2 Z -

Ether ice RedP

(A) CH3COOH (B) CH3MgI (C) CH3COCl (D) ClCH2COOH

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34. Ethyl alcohol can be obtained in one step from acetic acid by reduction with -
(A) Zinc and acetic acid (B) Lithium aluminium hydride
(C) HI and red phosphorus (D) Nickel and hydrogen

35. Kolbe’s electrolysis of aqueous potassium ethanoate leads to the formation of -

(A) Ethene (B) Methane (C) Ethane (D) Ethyne

36. When a bee bites, it mainly injects into body :

(A) Formic acid (B) Acetic acid (C) Carbonic acid (D) Hydrochloric acid

37. Carboxylic acids do not give the characterstic properties of -

(A) R – group (B) – COOH group (C) > C = O group (D) None is correct

38. In the molecule CH3CHCl – CH2COOH, Cl atom is attached to -

(A)  – Carbon atom (B) –Carbon atom (C) –Carbon atom (D) –Carbon atom

39. Which of the following test is not carried out to examin the presence of –COOH groups -
(A) Litmus test (B) Sodium bicarbonate test
(C) Ester test (D) Bromine water test

40. Reaction of a fat or oil with alkali is called -

(A) Esterification (B) Saponification (C) Etherification (D) Epoxidation

41. Which of the following lacks chirality -

(A) 2-Hydroxy propanoic acid (B) 2-Aminopropanoic acid
(C) 2,3-Butene-dioic acid (D) 2,3-Dihydroxy butanoic acid

42. (CH3)2C = CHCOCH3 can be oxidised to (CH3)2C = CHCOOH by -

(A) Chromic acid (B) NaOI (C) Cu at 300 ºC (D) KMnO4

43. Select the compound which does not give acetic acid on hydrolysis -
(A) CH3CCl3 (B) CH3CN (C) CH3COCl (D) CH3CH2Cl

44. The simplest dicarboxylic acid is -

(A) Vinegar acid (B) Carbolic acid (C) Oxalic acid (D) Succinic acid

45. The acid formed when propyl magnesium bromide is treated with CO2 is -
(A) CH3CH2COOH (B) C3H7COOH
(C) CH3CH2CH2CH2COOH (D) None

46. Which of the following skeleton gives the strongest acid if COOH is attached to the free valency -
C
|
(A) C – C – (B) C – C – C – (C) H – (D) C – C –

red P LiAlH4
47. A  CH3COOH    B. What is not true for A and B -
HI

(A) A is hydrocarbon of general formula CnH2n+2 while B belongs to alkanol

(B) A can be obtained by reducing CH3CH2Cl while B by its hydrolysis
(C) A is alkene while B is alkanal
(D) A and B both belongs to different homologous series

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 12
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
 Heat Heat
48. The product A, B, C and D in the reaction A + B   H – COOH   C + D are given
H2 SO 4

by the set -
(A) CO, H2O, CO2, H2 (B) CO2, H2O, CO, H2
(C) CO2, H2, CO, H2O (D) CO, H2, CO 2, H2O

49. Ozonolysis of fatty acid is carried out to ascertain -

(A) Number of –OH group (B) Number of – COOH group
(C) Position of carbonyl group (D) Position of double bond

50. Dry distillation of calcium acetate gives -

(A) Acetaldehyde (B) Acetone (C) Ethane (D) Propanal

1. When crystalline oxalic acid is heated to 110º with ... a monocarboxylic acid containing one carbon
atom is obtained -
(A) 1,2-Propane diol (B) Ethylene glycol (C) 1,2,3-Propane triol (D) Glyoxal

2. Ka will have the highest value for which of the following acids. -
(A) Fluoroacetic acid (B) Trichloroacetic acid
(C) Trimethyl acetic acid (D) Lactic acid

3. red
 P
 [ Product ] The product of the above reaction is -


(A) -Dibromo acid (B) ,’ - Dibromo acid

(C) ,’,’’-Tribromo acid (D) No reaction takes place

4. HVZ reaction is specific for -

(A) Replacement of  - hydrogen (B) Replacement of  - hydrogen
(C) Replacement of  - carbons (D) Replacement of  - carbons

5. Bifunctional organic compound is -

(A) HCOOH (B) CH3COOH (C) (CH3)2CO (D) HCHO

6. Acetic acid vapours when passed over aluminium phosphate forms -

(A) CH3CHO (B) Ketene (C) C2H6 (D) C2H4

7. The rate of esterfication of acetic acid with methyl alcohol (I), ethyl alcohol (II) , isopropyl alcohol (III)
and tert. butyl alcohol (IV) follows in the order -
(A) I > II > III > IV (B) IV > III > II > I (C) II > I > IV > III (D) III > IV > I > III

8. Arrange the following compounds in decreasing order of acidity -

ClCH2CH2CH2COOH CH3CHClCH2COOH CH3CH2CHClCOOH
I II III
(A) I > II > III (B) III > II > I (C) I > III > II (D) III > I > II

9. Arrange OHCH2COOH ( I ), HOCH2CH2COOH (II) and CH3COOH ( III ) in order of acidity -

(A) I > II > III (B) III > II > I (C) I > III > II (D) II > III > I

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 13
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
10. The rate of esterfication of HCOOH (I), CH3COOH (II), (CH3)2CHCOOH (III) and (CH3)3CCOOH (IV) with
ethanol follows in the order -
(A) IV > III > II > I (B) I > II > III > IV (C) II > I > IV > III (D) III > IV > I > II


11. X and Y in the reaction sequence R – C  N  H
3O
 X  diazomethane
  Y, are given by the set :
(A) Carboxamide , Carbonitrile (B) Carboxylic acid, Carbonitrile
(C) RCOOH, RCOOCH3 (D) RCONH2, RCOCH3

12. In the electrolysis of the aqueous solution of CH3CH2COONa, anion goes to anode the possibility of
formation of following compounds takes place -
(A) CH3 – CH2 – CH2 – CH3 (B) CH2 = CH2, CH3 – CH3
(C) CH3CH2COOC2H5 (D) All the above

13. Which of the following organic acid decolourises bromine water as well as forms anhydride -
(A) HOOC – COOH (B) HOOC – CH2 – COOH

(C) (D)

14. The general formula of dicarboxylic acid is -

(A) (COOH)2 (B) (CH2)n(COOH)2 (C) (CH2)n–2 (COOH)2 (D) (CH2)n–1 (COOH)2

15. The product A, B and C in the reaction sequence

 NaOH Heat
 A   B   C are -
360º C

(A) HCHO, HCOONa, CH3OH (B) HCHO, Na2CO 3, NaHCO3

(C) HCHO, HCOONa, (COONa)2 (D) HCHO, HCOONa, Na2CO 3

16. CH2COOH NaNO2 / HCl

 CH2COOH
| |
X Y
glycine glycollic acid
Here X and Y respectively are -
(A) OH, NH2 (B) NH2, OH (C) Cl, OH (D) None

17. The reagent used to step up in the homologous series of acids is -

(A) (CH3)2SO 4 (B) Diazomethane (C) CH3NH2 (D) CH3 – C  N

18. A compound with molecular formula C4H10O4 on acylation with acetic anhydride gives a compound with
molecular formula C12H18O 8. How many hydroxyl groups are present in the compound -
(A) One (B) Two (C) Three (D) Four

19. The carboxylic acid that does not undergo HVZ reaction is -
(A) CH3COOH (B) (CH3)2CHCOOH
(C) CH3CH2CH2CH2COOH (D) (CH3)3C COOH

20. The end product ‘C’ in the following sequence of chemical reactions is
CaCO
CH3COOH   3
 A heat NH2OH
 B   C -
(A) Acetaldehyde oxime (B) Formaldehyde oxime
(C) Methyl nitrate (D) Acetoxime

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 14
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
21. Which of the following carboxylic acids undergoes decarboxylation easily?
(A) C6H5 – CO – CH2 – COOH (B) C6H5 – CO – COOH
(C) C6H5 – CH – COOH (D) C6H5–CH–COOH
OH NH2

Cl2 Alc.KOH
22.  a   b
CH3CH2COOH 
red P

The compound b is -
(A) CH3CH2OH (B) CH3CH2COCl (C) CH2 = CHCOOH (D) CH3 – CHCl – COOH

23. A compound undergoes the following sequence of reactions :

Hydrolysis
Cl /P
C3H5N   C3H6O2 2
(a)
3 NH
C3H5O2Cl   C3H7NO 2
(b) (c)
The compound C is -
(A) 1-Nitropropane (B) 2-Nitropropane
(C) 2-Aminopropanoic acid (D) 2-Hydroxypropanamide

24. R – CH2 – CH2OH can be converted into RCH2CH2COOH. The correct sequence of reagent is
(A) PBr3, KCN, H+ (B) PBr3, KCN, H2 (C) KCN, H+ (D) HCN, PBr3, H+

25. The correct order of decreasing acid srength of trichloroacetic acid (a), trifluoroacetic acid (b), acetic
acid (c), and formic acid (d) is -
(A) a > b > c > d (B) a > c > b > d (C) b > a > d > c (D) b > d > c > a

26. Which of the following compounds will react with NaHCO3 solution to give sodium salt and carbon
dioxide -
(A) Acetic acid (B) n-Hexanol (C) Phenol (D) Both (B) and (C)

27. Which of the following statements are false about HCOOH -

(A) It is a stronger acid than CH3COOH
(B) It forms formyl chloride with PCl5
(C) It gives CO and H2O on heating with conc. H2SO 4
(D) It reduces Tollen’s reagent

28. The only acid which contains a carboxylic group is -

(A) Sulphanilic acid (B) Picric acid (C) Carbonic acid (D) Glycine

29. Which of the following acid does not form anhydride -

(A) Formic acid (B) Acetic acid (C) Propanoic acid (D) Phthalic acid

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 15
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
30. In a set of the given reactions, acetic acid yields a product C -
C H C H MgBr
 B 25
6 6
CH3COOH + PCl5  A   C Product C would be -
Ether Anhy. AlCl3

C2H5
(A) CH3CH(OH)C2H5 (B) CH3COC6H5 (C) CH3CH(OH)C6H5 (D) CH3–C–(OH)C6H5

31. Lactic acid, CH3CH(OH)COOH molecule shows -

(A) Geometrical isomerism (B) Metamerism
(C) Optical isomerism (D) Tautomerism

32. In the given reaction final compound (C) is-

O
(i)NaOH/  NaOH
CO2Et     (A) (B)  (C)
(ii)H3 O

OH
O
OH
(A) (B) (C) (D)
OHO OH O
O

33. Methyl malonic acid on heating to 160°C yields -

(A) Formic acid (B) Propanoic acid (C) CO + CO2 (D) Acetic acid

34. Which of the following sets of reagents X & Y will convert propanoic acid into alanine (an amino acid)?


O Br O NH3
X Y
CH3–C–OH CH3–CH–C–OH CH3–CH–COO–

X Y
(A) Br2 NaNH2
(B) Br2/P NaOH
(C) Br2/P NH3
(D) Br2/HBr NaNH2

35. Formic acid and formaldehyde can be distinguished by treating with -

(A) Benedict’s solution (B) Tollen’s reagent
(C) Fehling’s solution (D) NaHCO3

36. Which of the following has the highest pKa value ?

O O + O O
NMe3
(A) (B) NO2 (C) (D) NC
OH OH OH OH

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 16
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
37. (A), (B) and (C) are three dicarboxylic acids such that -

(a)  carboxylic acid + CO2  
(b)  acid anhydride + H2O 

(c)  cyclic ketone + H2O + CO 2 
then :
(a) (b) (c)
(A) adipic acid malonic acid succinic acid
(B) Malonic acid adipic acid succinic acid
(C) adipic acid succinic acid malonic acid
(D) Malonic acid succinic acid adipic acid

Statement based Questions

Each of the questions given below consist of Statement – I and Statement – II. Use the following
Key to choose the appropriate answer.
(A) If both Statement- I and Statement- II are true, and Statement - II is the correct explanation
of Statement– I.
(B) If both Statement - I and Statement - II are true but Statement - II is not the correct explanation
of Statement – I.
(C) If Statement - I is true but Statement - II is false.
(D) If Statement - I is false but Statement - II is true.

1. Statement I : Acetic acid does not give haloform reaction.

Statement II : Acetic acid has no -hydrogen.

2. Statement I : Formic acid reduces mercuric chloride solution.

Statement II : Formic acid has reducing aldehydic group.

3. Statement I : (CH3)3C–COOH does not give HVZ reaction.

Statement II : It does not have any -hydrogen.

4. Statement I : Carboxylic acids have a carbonyl group but it does not give the test of carbonyl group.
Statement II : Due to resonance, the bond character of group is greatly reduced.

5. Statement I : Carboxylic acids

 
 O 
 ||  have a carbonyl group but it does not give the test of carbonyl group.
 R – C – OH 
 

O
Statement II : Due to resonance the double, bond character of C group is greatly reduced.

6. Statement I : Acetic acid does not give haloform reaction.

Statement II : Acetic acid has no -hydrogen]

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 17
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
Passage based Questions

Passage-1 (Q. 7 to 9)
Carboxylic acids having at least one -hydrogen react with Cl2 or Br2 in the presence of phosphorus (or a
phosphorus halide) to give -halo acids. This reaction is known as Hell-Volhard-Zelinsky reaction (HVZ
reaction),
Br
P / Br2
R–CH2–COOH  R–CH–COOH
The HVZ reaction is limited to the formation of -chloro and -bromo acids and it is sometimes awkward to
carry out. The reagents (X2 and P) are noxious and the reaction time is often long and the conditions of
reaction are harsh.

7. Which of the following carboxylic acids will not give HVZ reaction ?

CH3 CH3
(A) CH3–COOH (B) CH 3–CH–COOH (C) CH3–CH2–COOH (D) CH3–C–COOH
CH3

8. Which of the following will be obtained when acetic acid is subjected to HVZ reaction ?

Br Br
(A) BrCH2COOH (B) Br–C–COOH (C) Br–C–COOH (D) All of these
H Br


9. CH3–COOH Br
2 /P (A) NaCN (B)
  HOH/H
 . The product (C) will be :

COOH CH2–COOH CH 2–CO CO

(A) CH 2 (B) (C) O (D) CH3–CH O
COOH CH 2–COOH CH 2–CO CO

Passage-2 (Q. 10 to 14)

Variety of products are obtained when dicarboxylic acids are heated. The nature of products depends
on the carbon chain length separating the two carboxylic groups.
(I) 1,2 and 1,3-dibasic acids on heating give monocarboxylic acid.

(II) 1,4 and 1,5-dibasic acids on heating give cyclic anhydride.

(III) 1,6 and 1,7-dibasic acids give cyclic ketones.

Indicate whether the following reactions are right or wrong.

COOH 200 C
10.  CO 2 + CO + H2O
COOH
Oxalic acid
(A) Right (B) Wrong

COOH 
CH3COOH  CO 2 
11. CH2 
COOH Acetic acid
Malonic acid
(A) Right (B) Wrong

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 18
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
 H–C–COOH 
12.  CH2  CH – COOH  CO 2
H–C–COOH
Malaic acid Crotonic acid
(A) Right (B) Wrong

COOH 
13. (CH2)4 
COOH
Cyclohexanone
Adipic acid
(A) Right (B) Wrong

CH2–COOH CH2–CO
14. 
 O + H2O
CH 2–COOH CH2–CO
Succinic acid Succinic anhydride

(A) Right (B) Wrong

True/False

15. The IUPAC name of acetic acid is methanoic acid.

16. Hell-Volhard-Zelinsky reaction is given by those acids which have -hydrogen.

17. All the C–O bond lengths in carboxylate ions are identical.

18. Formic acid acts as a reducing agent while acetic acid does not show this property.

Match the following

Q.19 Match the Column

(A) Acetic acid (1) Soda lime (M) ClCH2COOH

(B) Formic acid (2) Poisonous (N) Dicarboxylic acid
(C) Decarboxy- (3) Phosphorus (O) Soap lation
(D) Hell-Volhard (4) Kolbe’s (P) Fermentation of
-Zelinsky synthesis sugar reaction
(E) Oxalic acid (5) Saponification (Q) Carbon monoxide
(F) Electrolysis (6) Vinegar (R) Alkane of CH3COOK
(G)CH3COOC2H5 (7) Dehydration (S) Reducing acid + NaOH
(H) Formic acid (8) Red ants (T) Ethane + conc. H2SO 4

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 19
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
 PART - A : IIT-JEE PROBLEMS (PREVIOUS YEARS)

1. The major product of nitration of Benzoic acid is - [IIT-1993]

(A) 3-Nitrobenzoic acid (B) 4-Nitrobenzoic acid
(C) 2-Nitrobenzoic acid (D) 2,4-Dinitrobenzoic acid

I LiAlH 4
2. The organic product formed in the reaction C6H5COOH  
II H O 
[IIT-1995]
2

(A) C6H5CH2OH (B) C6H5COOH & CH4

(C) C6H5CH3 & CH3OH (D) C6H5CH3 & CH4

3. Which of the following carboxylic acids undergo decarboxylation easily – [IIT-1995]

(A) C6H5CO — CH2COOH (B) C6H5COCOOH

(C) C6H5 — COOH (D) C6H5 CH2 — COOH

|
NH2

4. The molecular weight of benzoic acid ;in benzene as determined by depression in freezing point method
corresponds to – [IIT-1996]
(A) Ionization of benzoic acid (B) Dimerisation of benzoic acid
(C) Trimerisation of benzoic acid (D) Solvation of benzoic acid

Br2 NH3 ( alc.)

5. CH3CH2COOH  X    Y.. Y in the above reactions is - [IIT-1996]
Re d P

(A) Lactic acid (B) Ethylamine (C) Propylamine (D) Alanine

6. When propionic acid is treated with aqueous NaHCO3, CO2 is librated. The ‘C’ of CO2 comes from -
[IIT-1999]
(A) Methyl group (B) Carboxylic acid group
(C) methylene group (D) bicarbonate

7. Benzoyl chloride is prepared from benzoic acid by – [IIT- 2000]

(A) Cl2, h (B) SO2Cl2 (C) SOCl2 (D) Cl2, H2O

8. Which of the following acids has the smallest dissociation constant ? [IIT- 2002]
(A) CH3CHFCOOH (B) FCH2CH2COOH (C) BrCH2CH2COOH (D) CH3CHBrCOOH

Acidic
9.   Products formed by P & Q can be differentiated by [IIT- 2003]
Hydrolysis

(A) 2 & 4 DNP (B) Lucas reagent (ZnCl2) conc. HCl

(C) NaHSO3 (D) Fehlings solution

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 20
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
Passage (Q.10 to Q.12)
In the following reaction sequence, products I, J and L are formed. K represents a reagent.

1. Mg / ether
1. NaBH
. CO2 K H
Hex-3-ynal   
4
 I 2   J  Me
2
Cl  L [IIT-2008]
2. PBr3 3. H3O  Pd/BaSO4
quinoline
O

10. The structure of the product I is-

Me
(A) Me Br
(B) (C) Me Br
(D) Me Br
Br

11. The structures of compounds J and K, respectively, are-

OH
(A) Me COOH and SOCl2 (B) Me and SO2Cl2
O

(C) Me and SOCl2 (D) Me COOH and CH3SO2Cl

COOH

12. The structure of product L is-

CHO
(A) Me CHO (B) Me (C) (D) Me CHO
CHO Me

13. The compound that does NOT liberate CO2, on treatment with aqueous sodium bicarbonate solution, is :
[JEE Advanced_2013-P-1]
(A) Benzoic acid (B) Benzenesulphonic acid
(C) Salicylic acid (D) Carbolic acid (Phenol)

14. The total number of carboxylic acid groups in the product P is : [JEE Advanced_2013-P-1]

Paragraph for Question Nos. 15 to 16

P and Q are isomers of dicarboxylic acid C4H4O4. Both decolorize Br2/H2O. On heating, P forms the cyclic
anhydride.
Upon treatment with dilute alkaline KMnO4, P as well as Q could produce one or more than one from S, T and
U. [JEE Advanced_2013-P-2]

S T U

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 21
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
15. In the following reaction sequences V and W are, respectively :
H2 /Ni
Q 
 V

(A) and

V W

(B) and

V W

(C) and

V W

(D) and

V W

16. Compounds formed from P and Q are, respectively :

(A) Optically active S and optically active pair (T, U)
(B) Optically inactive S and optically inactive pair (T, U)
(C) Optically active pair (T, U) and optically active S
(D) Optically inactive pair (T, U) and optically inactive S

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 22
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
 PART - B : AIEEE PROBLEMS (PREVIOUS YEARS)

1. End product of the following reaction is – [AIEEE-2002]

CH3CH2COOH

(1) CH3CHCOOH (2) (3) CH2 = CHCOOH (4)

OH

2. In the anion HCOO— the two carbon-oxygen bonds are found to be of equal length. What is the reason for it ?
[AIEEE-2003]
(1) The anion HCOO— has two resonating structures
(2) The anion is obtained by removal of a proton from the acid molecule
(3) Electronic orbitals of carbon atom are hybridised
(4) The C=O bond is weaker than the C—O bond

3. Which one of the following does not have sp2 hybridized carbon ? [AIEEE-2004]
(1) Acetone (2) Acetic acid (3) Acetonitrile (4) Acetamide

4. Consider the acidity of the carboxylic acids : [AIEEE-2004]

(a) PhCOOH (b) o – NO2C6H4COOH (c) p – NO2C6H4COOH (d) m – NO2C6H4COOH
Which of the following order is correct ?
(1) a > b > c > d (2) b > d > c > a (3) b > d > a > c (4) b > c > d > a

5. The compound formed as a result of oxidation of ethyl benzene by KMnO 4 is : [AIEEE-2007]

(1) benzophenone (2) acetophenone (3) benzoic acid (4) benzyl alcohol

6. A liquid was mixed with ethanol and a drop of concentrated H2SO4 was added. A compound with a fruity smell
was formed. The liquid was : [AIEEE-2009]
(1) CH3OH (2) HCHO (3) CH3COCH3 (4) CH3COOH

NCERT QUESTIONS

1. Arrange the following compounds in increasing order of their property as indicated :

(i) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone (reactivity towards HCN)
(ii) CH CH CH(Br)COOH, CH CH(Br)CH COOH, (CH ) CHCOOH, CH CH CH COOH (acid strength)
3 2 3 2 3 2 3 2 2
(iii) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength)

2. How will you prepare the following compounds from benzene? You may use any inorganic reagent and any
organic reagent having not more than one carbon atom
(i) Methyl benzoate (ii) m-Nitrobenzoic acid (iii) p-Nitrobenzoic acid
(iv) Phenylacetic acid (v) p-Nitrobenzaldehyde.

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 23
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
3. How will you bring about the following conversions in not more than two steps?
(i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde
(iii) Ethanol to 3-Hydroxybutanal (iv) Benzene to m-Nitroacetophenone
(v) Benzaldehyde to Benzophenone (vi) Bromobenzene to 1-Phenylethanol
(vii) Benzaldehyde to 3-Phenylpropan-1-ol
(viii) Benazaldehyde to -Hydroxyphenylacetic acid
(ix) Benzoic acid to m- Nitrobenzyl alcohol

4. Complete each synthesis by giving missing starting material, reagent or products.

(ii) (vi)

5. Give plausible explanation for each of the following :

(iii) During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid catalyst,
the water or the ester should be removed as soon as it is formed.

6. An organic compound contains 69.77% carbon, 11.63% hydrogen and rest oxygen. The molecular mass of
the compound is 86. It does not reduce Tollens’ reagent but forms an addition compound with sodium
hydrogensulphite and give positive iodoform test. On vigorous oxidation it gives ethanoic and propanoic acid.
Write the possible structure of the compound.

7. Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a
stronger acid than phenol. Why?

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 24
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU
 EXERCISE - 1

Qus. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25
Ans. B A B B C A A C C B D C D B D A A B D A B D C A C
Qus. 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50
Ans. B D D C C D C D B C A C B D B C B D C B C C C D B

EXERCISE - 2

Qus. 1 2 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25
Ans. C B D B A B A B A B C D C B C B B D D D A C C A
Qus. 26 27 28 29 30 31 32 33 34 35 36 37 38
Ans. C A B D A D C D B C D A D

EXERCISE - 3

Q.No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18
Ans. C A A A A C D D A A A B B A FALSE TRUE TRUE TRUE
Q.No. 19
Ans. A -6-P, B-8-S, C-1-R, D-3-M, E-2-N, F-4-T ,G-5-O, H-7-Q

EXERCISE - 4

SECTION-A

Q.No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16
Ans. A A A B D D C C D D A C D 2 A B

SECTION-B

Q.No. 1 2 3 4 5 6
Ans. 3 1 3 2 3 4

Physical & Inorganic By Organic Chemistry By

A-479 Indra vihar, kota Carboxylic Acid_Advanced # 25
NV Sir Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) VKP Sir
B.Tech. IIT Delhi M.Sc. IT-BHU