TUTORIAL 17 : CARBOXYLIC ACID AND ITS DERIVATIVES

17.1 Introduction to carboxylic acids

At the end of the topic, students should be able to:
a) Give the general formula of carboxylic acids.
b) Draw the structures and name the carboxyl compounds (parent chain C10) according to the IUPAC
nomenclature.
c) Give common names with parent chain C5.
d) Explain the physical properties :
i. Boiling point
ii. Solubility in water and in organic solvents.
e) Explain the acidity of:
i. Carboxylic acid in comparison with alcohol and phenol.
ii. Halogenated carboxylic acids based on the
Number of halogens
Position of halogens

1. Give the IUPAC names for the following carboxylic acids:

(a) CH3(CH2)5CO2H
(b) O

OH

(c) CH3(CH2)4CH(COOH)2
(d) CH2 CH3 O
CH CH2 CH2 CH2 CH2 C OH

(e) CH2 CH3

CH3 CH CH2 C OH
O

2. Draw the structural formula for each of the following compounds:

(a) 2-hydroxy-2-phenylethanoic acid
(b) 2-chlorobutanedioic acid
(c) o-hydroxybenzoic acid
3. Arrange the following compounds in order of increasing acidity and explain your
answer.
(a) CH2ClCOOH, CH3COOH, CH3CH2OH, CH2FCOOH, CHF2COOH
(b) Ethanoic acid, phenol, 2-chloroetanoic acid and ethanol

4. Arrange the following compounds in order of increasing boiling point. Explain your
answer.
pentanal, butanoic acid, pentane, 1-butanol

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17.4 Preparation of carboxylic acids

At the end of the topic, students should be able to:
a) Explain the preparation of carboxylic acid through:
i. Oxidation of alkylbenzene,alcohol and aldehyde.
ii. Hydrolysis of nitrile compound
iii. Carbonation of Grignard reagent.

17.5 Chemical properties of carboxylic acids

At the end of the topic, students should be able to:
a) Explain the chemical properties with reference to:
i. Neutralization with a base
ii. Reaction with electropositive metals such as Na, K, Mg or Ca.
iii. Reduction with LiAlH4 followed by H3O+
iv. Acyl chloride formation.
v. Anhydride formation
vi. Esterification
vii. Amide formation.
b) Explain the reducing property of methanoic acid with:
i. KMnO4/H3O+
ii. Tollens reagent

5. Identify compounds A-F in the following reactions.

(a) Cl
i. KMnO4, OH,
CH3 CH CH2 CHO A
ii. H+

(b) +
K2Cr 2O7 , H
CH3 CH2 CH2OH B

(c) C + NaOH CH3CH2COONa + H2O

(d) H SO ,
CH3OH + D 2
4
CH3CH2COOCH3 + H2O

(e) CH 2COOH E CH 2COCl

+ HCl + SO 2

(f) i) LiAlH4/ether
CH 3CH 2COOH
ii) H3O+ F

g) excess
G H

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TUTORIAL 17 : CARBOXYLIC ACID AND ITS DERIVATIVES

SOCl2
h) CH3CH2COOH
Pyridine

Mg
i) CH3CH2CH2COOH

6. Based on the reaction scheme below:

O O
R
CH2 C O CH2 CH3 CH2 C OH
+

+
H2O, H SOCl 2

M+N K M
(a) Draw the structural formulae for compound M.
(b) Give reagent R.

7. Show how propanoic acid may be converted to each of the following compounds:
(a) CH3CH2CH2COOH
(b) O
CH3 CH2 CH2 CH2 O C CH2 CH3
(c) O
CH3 CH2 C Cl
(d) 2-propanol

8. An Organic compound, P has the molecular formula, C3H6O. It reacts with Cr2O72-/H+
to form Q. Q reacts with ethanol to give sweet smelling liquid, R. The reaction is
catalyst by concentrated sulphuric acid.
i) Identify P, Q and R. Write the equation for the reaction involved.
ii) Suggest suitable Grignard reagent can be used to produce Q

9. Explain why methanoic acid give positive result with Tollens Test and acidified
potassium permanganate but ethanoic acid does not.

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OBJECTIVE QUESTIONS
1. The reaction between ethanoic acid and ethanol in the presence of a little concentrated
sulphuric acid is an example of
A. oxidation
B. reduction
C. nucleophilic substitution
D. electrophilic substitution

2. Which compound does NOT react with acidified potassium permanganate solution at
70C?
A. Ethanol
B. Cyclohexene
C. Methanoic acid
D. 2-Methyl-2-butanol

3. Which of the following is the most suitable method for preparing benzoic acid from
ethyl benzene?
A. Boiling with concentrated HNO3
B. Boiling with alkaline KMnO4 followed by acidification
C. Addition of Cl2 in the presence of sunlight followed by NaOH in CH3CH2OH
D. Addition of Cl2 in the presence of sunlight followed by boiling with aqueous
NaOH

4. Which of the following acids is the most soluble in water?

A. Benzoic acid
B. Butanoic acid
C. Heptanoic acid
D. 1,4-benzenedicarboxylic acid

5. Which of the following would react with benzoic acid to produce benzoyl chloride?
A. Cl2
B. HCl
C. NaCl
D. SOCl2

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6. Which of the following is the best reagent(s) for the following conversion?

COOH CH 2OH

A. H2, Pt
B. KMnO4, H+
C. LiAlH4 followed by acidification
D. NaBH4 followed by acidification

7. Which of the following is the correct order of decreasing acidity?

A. FCH2COOH > CH3COOH > F2CHCOOH
B. F2CHCOOH > Cl2CHCOOH > CH3COOH
C. CH3COOH > ClCH2COOH > FCH2COOH
D. CH3COOH > ClCH2COOH > BrCH2COOH
8. What happen when methanoic acid is heated with concentrated H2SO4?
A. An ester is formed.
B. Methane is produced.
C. Methanol is produced.
D. Carbon dioxide is released.

9. Which of the following reagents would distinguish benzoic acid from methanoic acid?
A. PCl5
B. NaOH
C. H2CrO4
D. Na2CO3
10. Which of the following is an ester?
A. CH3COCH2OH
B. CH3COCOCH3
C. HCO2CH(OH)CH3
D. HOCH2CH2COOH

11. What alcohol is used in the manufacturing of the following ester?

OH CH3
Br CH2 CH COOCH CH3
A. methanol
B. 2-propanol

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C. 2-bromoethanol
D. 3-bromo-1,2-propanediol

12. How many isomers are there for an acyl chloride with the molecular formula of
C4H9COCl?
A. 3
B. 4
C. 5
D. 6

13. Salicylic acid is used in the production of aspirin via the following route.
COOH COOH
X

OH OCOCH 3
X could be
A. CH3OH
B. CH3COOH
C. (CH3CO)2O
D. CH3CONH2

Summary of options
A B C D
I only I and II only II and III only I, II, and III

14. Which of the following acid would decolourise acidified KMnO4 solution under a
suitable condition?
I. Methanoic acid
II. Benzenedicarboxylic acid
III. Cyclohexanecarboxylic acid

15. Which of the following is/are correct regarding to the compound below?
CH 2OH
HO C COOH
OH

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I. It exists as a pair of enantiomers.

II. 1 mole of the compound would react with 3 moles of PCl5
III. 1 mole of the compound would react with 2 moles of sodium hydroxide

16. Which of the following would produce an acid chloride when treated with SOCl2?
I. CH3CH2OH
II. O O
HO C C OH
III.
HOOC COOH

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