CARBOXYLIC ACIDS & THEIR DERIVATIVES

EXERCISE

Section A

1. A 1.0 dm3 sealed container which is half-filled with liquid is left at a fixed temperature until
equilibrium. Which liquid would produce the lowest saturated vapour pressure?
A 1-propanol C Propanone
B Ethanoic acid D Propanal

2. Which organic compound forms white fumes with PCl5, forms bubbles with Na2CO3 and decolourises
acidified KMnO4 solution?
A HCOOH C CH3CH2OH
B CH3COOH D C6H5OH

3. Ethanoyl chloride reacts with excess methanamine to form an organic compound, X. Which
statement is true?
A N,N-dimethylethanamide is also formed in the reaction.
B X reacts with hydrochloric acid to form ethanoic acid.
C The reaction mechanism is nucleophilic addition.
D X is a primary amide.

4. Which is the product of the reaction between phenylmethanol and ethanoyl chloride?
A C6H5CH2COCl C C6H5CH2COOCH3
B CH3COOC6H5 D CH3COOCH2C6H5

5. An ester extracted from bananas has the structure formula, CH3COOCH2CH(CH3)CH2CH3. What are
the products formed if the ester is reacted with LiAlH4 followed by hydrolysis?
A CH3CHO and HOCH2CH(CH3)CH2CH3
B CH3COOH and HOCH2CH(CH3)CH2CH3
C CH3OH and HOCH2CH2CH(CH3)CH2CH3
D CH3CH2OH and HOCH2CH(CH3)CH2CH3

6. The structure formula for panthenol is shown below.

Two compounds are formed when panthenol is hydrolysed in an aqueous alkaline solution. Which
reagent can differentiate both compounds?
A SOCl2 C KMnO4/H+
B NaNO2/HCl D I2/NaOH(aq)
7. An organic compound, X, has the structural formula CH3COOCH2CH(CH3)CH2CH3 . Which statement is
true about X?
A It react with LiAlH4 to form two alcohols.
B Its IUPAC name is pentyl ethanoate.
C It has a high boiling point.
D It is optically inactive.

8. A structure formula of acetaminophen is shown below

Which statement is not true about the compound?

A Its IUPAC name is N-phenylethanamide.
B It forms a salt with sodium hydroxide solution.
C It form two organic compounds with hot hydrochloric acid.
D It undergoes electrophilic substitution reaction with bromine water.

Section B

1. a) 2,2-dimethylbutanoic acid is an organic compound.

i) Draw the structural formula of 2,2-dimethylbutanoic acid. (1m)
ii) Draw the structural formula of an optically active isomer 2,2-dimethylbutanoic acid with a
fruity smell and write its IUPAC name. (2m)
iii) Which isomer has a higher boiling point? Explain your answer. (2m)
b) An aromatic compound, X, C7H7NO2 has acidic and basic functional groups.
i) Draw the structural formula of X. (1m)
ii) What is the number of pi bonds in a molecule of X? (1m)
iii) State one important property of an aqueous solution of X. (1m)

2. Citric acid is found in grapes and oranges. It is often used as a chelating agent to remove limescales
from industrial boilers. The structure of citric acid is shown below.

a) Give IUPAC name for citric acid. (1m)

 b) Citric acid can be prepared through a two-step synthesis from a compound, P, using the
following reaction scheme.
Step 1 Step 2
HOC(CH2Cl)2COOH Q Citric acid

i) Draw the structural formula of Q. (1m)

ii) Give reagents and reaction conditions for step 1 and step 2. (2m)
c) Explain why citric acid is stronger acid compared to ethanoic acid in an aqueous solution.(3m)
d) State one usage of citric acid other than as a chelating agent. (1m)

3. Banana oil contains isoamyl acetate, a naturally occurring ester which gives ripe bananas their
characteristic odour. The structure of isoamyl acetate is shown below.

a) Name isoamyl acetate according to IUPAC name. (1m)

b) By using a reaction scheme, show the three-steps synthesis to produce banana oil from ethane.
State also the reagents and reaction conditions. (5m)
c) Ethanol and C5H12O are formed by the reduction reaction of banana oil. Draw the structure of
C5H12O and state the reducing agent used. (2m)

4. a) The reaction scheme for the preparation of 3-nitrobenzoic acid from benzene is shown below.

CH2CH3 COOH COOH

X Y Z

NO2

Identify reagents X, Y and Z. (3m)

b) Propanamide is one of the derivative of carboxylic acid.
i) Write the structural formula of the propanamide. (1m)
ii) Write a chemical equation for the preparation of the propanamide from a carboxylix acid.
(2m)
iii) Write the IUPAC name from the most reactive derivative of the carboxylic acid. (1m)