MDCAT

Chemistry
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 Carboxylic Acid
Learning Objectives:
Nomenclature
Classification
Physical Properties
Preparation
Reactivity
Nomenclature of Carboxylic acid:
The aliphatic monocarboxylic acids are commonly called fatty acids because higher
members of this series such as palmitic acid (C15H31COOH) stearic acid (C17H35COOH),
etc. are obtained by the hydrolysis of fats and oils.

Common names:
▪ The common names of carboxylic acids were derived from the source from which they
are isolated.
▪ The irritation caused by an ant bite is due to formic acid (Latin word formica, ant).
▪ It was first isolated by the distillation of red ants.
▪ Acetic acid was first isolated from vinegar and butyric acid was named after butyrum
means butter.
▪ The positions of other groups attached with the chain containing the carboxyl group are
indicated by the Greek letters 𝛼, 𝛽, 𝛾, 𝛿 etc.
▪ The carbon adjacent to carboxylic group is 𝛼 carbon.

The IUPAC Nomenclature:

▪ The IUPAC names of saturated monocarboxylic acids are alkanoic acids.
▪ These are derived from the names of the alkanes containing the same number of
carbon atoms as the acid.
▪ The ending “e” of the alkane name is dropped and suffix-oic acid is added.
▪ Thus acetic acid gets the name ethanoic acid.
Trimethyl acetic acid n-valeric acid (Pentanoic acid)

Oxalic acid Malonic acid

(Ethanedioic acid) (propanedioic acid)

Succinic acid (Butandioic acid) Glutaric acid (pentandioic acid)

Adipic acid (Hexandioic acid)

Benzoic acid Phthalic acid (1,2-benzendioic acid)

Physical properties:
▪ The polar nature of both the O-H and C=O bonds results in the formation of strong
hydrogen bonds with other carboxylic acid molecule or other hydrogen bonding
systems.
▪ The first three aliphatic acids i.e. formic acid, acetic acid and propionic acid are
colourless liquids and have pungent smell. The next three acids C4 to C6 are colourless
liquids with somewhat unpleasant smell.
▪ Among the aliphatic acids, the first four members are very soluble in water due to
hydrogen bonding.
▪ The boiling points of carboxylic acids are relatively high due to intermolecular hydrogen
bonding.

▪ The molecular mass determination in non-polar solvent like benzene shows that
Carboxylic acids exist as cyclic dimers.

▪ It has been observed that the melting points of carboxylic acids containing even number
of carbon atoms are higher than the next lower and higher members containing odd
number of carbon atoms
Preparation of carboxylic acid:
From Primary Alcohols and Aldehydes:
𝑂𝑥𝑖𝑑𝑎𝑡𝑖𝑜𝑛
▪ Primary alcohol/Aldehyde → carboxylic acid
▪ K2Cr2O7/H2SO4 is an oxidizing agent.

▪ Aldehydes are easily oxidised to corresponding carboxylic acids even by mild oxidizing
agents such as Tollen’s Reagent (Ammonical silver nitrate).

From alkyl nitrile:

▪ Compounds having a cyanide ( - C ≡ N) group are called nitriles.
▪ Hydrolysis of an alkanenitrile on boiling with mineral acids or alkalis yields
corresponding carboxylic acid.
▪ Alkanenitriles can be prepared by treating alkyl halide with alcoholic potassium cyanide.
 ▪ It may be noted that acid produced has one carbon atom more than the original alkyl
halide.

From Grignard’s reagent:

▪ Carboxylic acids can be prepared by the action of Grignard reagent with carbon dioxide.
▪ This reaction is either carried out by passing carbon dioxide through the ethereal
solution of corresponding Grignard reagent or by adding Grignard reagent to crushed
dry ice suspended in ether.
▪ The addition product on reaction with a mineral acid produces carboxylic acid.

By the hydrolysis of ester:

▪ The appropriate ester on boiling with concentrated sodium hydroxide yields sodium salt
of the acid.
▪ This resulting salt when treated with dilute HCl gives the free carboxylic acid.
By the oxidative cleavage of alkenes:
▪ Alkenes when heated with alkaline KMnO4 are cleaved at the double bond to form
carboxylic acids.

Reactivity of carbonyl group:

Carboxylic acids undergo the following type of reactions:
▪ The reaction in which hydrogen atom of the carboxyl group is involved.
▪ The reaction in which OH group is replaced by another group.
▪ The reactions involving carboxyl group as a whole.

Reactions involving H atom of carboxyl group:

➢ Carboxylic acids are weaker acids than mineral acids. They furnish H+ when dissolved in
water.

➢ In the presence of water (H2O), the proton breaks away as H3O+ ion.

Reactions with Bases:

➢ Carboxylic acid + Bases ⟶ Salts and water

Reactions with carbonates and bicarbonates:

➢ Carboxylic acid + Carbonates/bicarbonates ⟶ CO2 evolved with effervescence
Reaction with metals:
➢ Carboxylic acid + Active metals(Na, K, Ca and Mg)⟶ H2 gas

Reactions Involving the OH Group of Carboxylic Acids:

➢ Carbonyl group of aldehydes and ketones, is susceptible to attack by a nucleophile.
➢ The addition of a nucleophile to the carboxyl group is always followed by the
displacement of the OH group by some other group, producing a carboxylic acid
derivative.
➢ The OH group can thus be replaced by X, OR and NH2 to form halides, esters and
amides,respectively.

Preparation of acyl chloride:

➢ Acyl chlorides are prepared by treating the carboxylic acid with thionyl chloride (SOCl2)
in the presence of base.

Mechanism:
Formation of Ester:
➢ When carboxylic acids are heated with alcohols in the presence of concentratedH2SO4,
esters are formed.

Mechanism:
• Protonation of Carboxylic Acid:
• Attack of CH3 -CH2OH:
• Hydrogen Ion Transfer:
• Elimination of Water and H+

This reaction is also known as Fischer esterification.

Esters are obtained by refluxing the parent carboxylic acid with the appropriate alcohol with
an acid catalyst.
The equilibrium can be driven to completion by using an excess of either the alcohol or the
carboxylic acid, or by removing the water as it forms.
Alcohol reactivity order: CH3OH>10 >20>30
 Esters can also be made from other carboxylic acid derivatives, especially acyl halides and
anhydrides, by reacting them with appropriate alcohol in the presence of a weak base.
Esters have fruity smell and are used as artificial flavours.

Formation of amide:
➢ Carboxylic acids react with ammonia to form ammonium salts which on heating produce
acid amides.

Mechanism:
Formation of Acid Anhydride:
➢ Carboxylic acids are dehydrated on heating strongly in the presence of phosphorus
pentoxide.

Reactions involving carboxyl group:

Partial Reduction to Alcohols:
➢ Carboxylic acids on reaction with lithium aluminium hydride (LiAIH4) are reduced to
alcohols.

Complete reduction to alkanes:

➢ Carboxylic acids on reduction with HI and red phosphorus give alkanes.
 Assessment 1
1. Which of the following is dicarboxylic acid having chemical formulaH2 C2O4?
a. Acetic acid
b. Lactic acid
c. Malonic acid
d. Oxalic acid
2. Which of the following is obtained by the hydrolysis of fats/oils?
a. Stearic acid
b. Oxalic acid
c. Palmitic acid
d. Both a and c
3. The carboxylic acid in which two –COOH groups are attached to benzene ring is called:
a. Phthalic acid
b. Benzoic acid
c. Stearic acid
d. Palmitic acid
4. Propanedioic acid is the carboxylic acid which is commonly known as:
a. Oxalic acid
b. Methanoic acid
c. Malonic acid
d. Phthalic acid
5. The main acid which was first isolated from vinegar and butter are respectively:
a. Butyric acid and formic acid
b. Oxalic acid and acetic acid
c. butyric acid and acetic acid
d. Acetic acid and butyric acid
6. The oxidation of primary alcohol and Aldehyde to corresponding carboxylic acid is usually
carried out in:
a. Dry conditions
b. Acidic medium
c. Basic medium
d. Neutral
7. The compound (A) is made to react with NaOH on boiling forming sodium salt of acid which on
treatment with HCl yields acetic acid. The compound A is:
a. Ethyl magnesium bromide
b. Ethanol
c. Ethyl acetate
d. Acetaldehyde

8. Acetic acid (CH3COOH) which is dissolved in benzene shows a molecular mass of:
a. 30
b. 60
c. 120
d. 240
9. The carboxylic acids which are colourless liquids with somewhat unpleasant smell:
a. C1-C2
b. C2-C3
c. C1-C3
d. C4-C6
10. The significant solubility of aliphatic acids in water due to hydrogen bonding is exhibited by:
a. Formic acid only
b. Acetic acid only
c. Formic acid, acetic only
d. Formic acid, acetic acid, propanoic acid and butanoic acid
 Assessment 2
1. Which of the following carboxylic acid has higher melting point?
a. 1C containing carboxylic acid
b. 3C containing carboxylic acid
c. 4C containing carboxylic acid
d. 5C containing carboxylic acid
2. The gas which is released when acetic acid reacts with sodium carbonate:
a. Hydrogen gas
b. Carbon dioxide gas
c. Nitrogen gas
d. None of these
3. Which of the following is not the typical chemical property of aliphatic acid as an acid:
a. Reaction with carbon dioxide to release carbon dioxide gas
b. Reaction with Sodium metal to release hydrogen gas
c. Reaction with bases to form salts and water
d. All of these
4. Which of the following is not the product of reaction of acetic acid with phosphorous
pentachloride?
a. CH3COCl
b. POCl3
c. PCl3
d. HCl
5. The addition of a nucleophile to the carboxyl group is always followed by the:
a. Displacement of –OH group by other group producing alkene.
b. Displacement of –OH group by other group producing carboxylic acid derivative.
c. Displacement of –OH group by other group producing ester.
d. Displacement of –OH group by other group producing alkyl nitrile.
6. The reaction of acetic acid with thionyl chloride results in the release of gas:
a. Chlorine
b. Sulphur dioxide
c. Carbon dioxide
d. Hydrogen
7. Which of the following is not correctly related to each other?
a. Amylacetate-Banana
b. Octylacetate-Orange
c. Benzylacetate-Raspberry
d. Amylbutyrate-Apricot
8. Carboxylic acids react with ammonia to form ammonium salts which on heating produce:
a. CH3CONH2
b. CH3COONH2
c. (NH2)2 CO
d. All of these
9. Which of the following forms acetic acid when undergoes hydrolysis?
a. Ethanol
b. Acetamide
c. Methyl nitrile
d. Methanol
10. Which of the following is the product when two molecules of acetic acid are heated with P 2O5:
a. 2 mole of ethyl alcohol
b. 1 mole Formic anhydride
c. 1 mole of Acetic anhydride
d. 2 moles of methyl cyanide
 Assessment 3
1. Acetylene is treated with 20% H2SO4 and 1.0% HgSO4 at 80°C to give compound (X) which is
then oxidised using V2O5 to give product (Y). What is the name of compound (Y)?
a. Ethanal
b. Ethane
c. Acetic acid
d. Acetaldehyde

2. Acetic acid due to formation of hydrogen bonding is miscible with:

a. Water
b. Alcohol
c. Ether
d. All of these
3. The group which is present in waxes:
a. −𝑂 −
b. – 𝐶𝑂𝑂𝐻
c. −𝐶𝑂𝑂 −
d. – 𝐶𝑂 −
4. When acetamide is hydrolyzed by boiling with acid to form the product. The product obtained
is:
a. Ethylamine
b. Ethanol
c. Acetic acid
d. Acetone
5. The following is the general representation of acid anhydride:
a. 𝑅 − 𝐶𝑂𝑂 − 𝑅
b. 𝑅 − 𝐶𝑂 − 𝑅
c. 𝑅 − 𝑂 − 𝑅
d. (𝑅𝐶𝑂)2 𝑂
6. The following is the most reactive one in the following list:
𝐴 = (𝑅𝐶𝑂)2 𝑂, 𝐵 = 𝑅𝐶𝑂𝑋, 𝐶 = 𝑅𝐶𝑂𝑁𝐻2 , 𝐷 = 𝑅𝐶𝑂𝑂𝑅
a. A
b. B
c. C
d. D
7. The reaction of which of the following compound with sodium metal results in evolution of
hydrogen gas:
a. Ethanol
b. Acetic acid
c. Ethane
d. Both a and b
8. Two aromatic compounds; phenol and benzaldehyde are present in a solution. Which of the
following is mostly used to separate benzaldehyde from phenol in a given solution?
a. NaHCO3
b. Lime
c. NaOH
d. All of these
9. Acetic acid is manufactured by the fermentation of:
a. Methanol
b. Acetone
c. Ethanol
d. Ethanal
10. A fruity smell is produced by the reaction of ethanol in presence of mineral acid with:
a. Phosphorous pentachloride
b. Acetic acid
c. Acetaldehyde
d. Acetic anhydride
 Assessment 4
1. Which of the following carboxylc acid can not be yielded by the hydrolysis of an alkanenitrile
on boiling with mineral acids or alkalis :
a. Formic acid
b. Acetic acid
c. Propionic acid
d. None of these

2. In order to prepare carboxylic acid, Ethereal solution of Grignard reagent is made to react with
the following with the addition of mineral acid:
a. Water
b. Ammonia
c. Carbon dioxide
d. Formaldehyde
3. 2-Methylbut-2-ene on oxidation with hot alkaline KMnO4 solution form two products; A and B.
The product A and B are:
a. Methanoic acid and ethanoic acid
b. Ethanoic acid and Ethanoic acid
c. Ethanoic acid propanoic acid
d. Ethanoic acid and propanone
4. The statement which is true about the phthalic acid and oxalic acid is:
a. Both are aromatic
b. Both are dicarboxylic acids
c. Both are strong acids
d. All of these
5. Which of the following carboxylic acid is strong acid in water?
a. Methanoic acid
b. Ethanoic acid
c. Propanoic acid
d. All have same acidic strength
6. The aromatic compound which does not contain –COOH group is:
a. Benzoic acid
b. Phthalic acid
c. Carbolic acid
d. 2-chloro benzoic acid
 KEY
Assessment 1
1. D
2. D
3. A
4. C
5. D
6. B
7. C
8. C
9. D

10. D

Assessment 2
1. C
2. B
3. D
4. C
5. B
6. B
7. C
8. A
9. C
10. C
 KEY
Assessment 3
1. C
2. D
3. C
4. C
5. D
6. B
7. D
8. A
9. C
10. B

Assessment 4
1. A
2. C
3. D
4. B
5. A
6. C
7. C
8. B
9. B
10. D