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Worksheets

Carboxylic acids and their derivatives

Total questions: 25

Worksheet time: 1hrs 15mins

Name
Class
Date
1.

An excess of methanol was mixed with 12 g of ethanoic acid and an acid catalyst. At equilibrium the mixture contained 8 g of methyl ethanoate. The percentage yield of ester present was ...

a)

11

b)

20

c)

54

d)

67

2.

CH2O is the empirical formula of

a)

methanol

b)

methyl methanoate

c)

ethane-1,2-diol

d)

butanal

3.

Hydrolysis of the ester, CH3COOCH2CH2CH3, produces ethanoic acid. In an experiment, 2.04 g of the ester was used and 0.90 g of ethanoic acid was produced. The percentage yield of ethanoic acid was:

a)

44

b)

59

c)

75

d)

90

4.

How many structural isomers, which are esters, have the molecular formula C4H8O2?

a)

2

b)

3

c)

4

d)

5

5.

The structural formula of ethyl 2-methylpropanoate is ...

a)

A

b)

B

c)

C

d)

D

6.

The compound lithium tetrahydridoaluminate(III), LiAlH4, is a useful reducing agent. It behaves in a similar fashion to NaBH4. Carbonyl compounds and carboxylic acids are reduced to alcohols. However, LiAlH4 also reduces water in a violent reaction so that it must be used in an organic solvent. Which one of the following can be reduced by LiAlH4 to a primary alcohol?

a)

A

b)

B

c)

C

d)

D

7.

Acid hydrolysis of the molecule shown, produces ...

a)

CH3CH(OH)CH2CH2COOH

b)

CH2(OH)CH2CH2CH2COOH

c)

CH3CH(OH)CH2CH2OCHO

d)

CH2(OH)CH2CH2CH2OCHO

8.

Which compound is formed by the reaction of ethane-1,2-diol with an acid?

a)

A

b)

B

c)

C

d)

D

9.

Which one of the following types of reaction mechanism is not involved in the above sequence?

a)

free-radical substitution

b)

nucleophilic substitution

c)

elimination

d)

nucleophilic addition-elimination

10.

Ibuprofen is a drug used as an alternative to aspirin for the relief of pain, fever and inflammation. The structure of ibuprofen is shown. Which one of the following statements is not correct?

a)

It has optical isomers.

b)

It liberates carbon dioxide with sodium carbonate solution.

c)

It undergoes esterification with ethanol.

d)

It undergoes oxidation with acidified potassium dichromate(VI).

11.

Butan-1-ol was converted into butyl propanoate by reaction with an excess of propanoic acid. In the reaction, 6.0 g of the alcohol gave 7.4 g of the ester. The percentage yield of ester was

a)

57

b)

70

c)

75

d)

81

12.

Which one of the following would not react with aqueous silver nitrate to produce a precipitate that is soluble in concentrated aqueous ammonia?

a)

CaBr2

b)

[COCI4]2−

c)

(CH3)4N+I

d)

CH3COCl

13.

Which one of the following is not a correct general formula for the non-cyclic compounds listed?

a)

alcohols CnH2n+2O

b)

aldehydes CnH2n+1O

c)

esters CnH2nO2

d)

primary amines CnH2n+3N

14.

Which one of the following is not a correct statement about vitamin C, shown below?

a)

It is a cyclic ester.

b)

It can form a carboxylic acid on oxidation.

c)

It decolourises a solution of bromine in water.

d)

It is a planar molecule.

15.

Propanoic acid reacts with methanol in the presence of a small amount of concentrated sulphuric acid. The empirical formula of the ester formed is

a)

CH2O

b)

C2H6O2

c)

C2H4O2

d)

C2H4O

16.

In which one of the following mixtures does a redox reaction occur?

a)

ethanal and Tollens’ reagent

b)

ethanoyl chloride and ethanol

c)

ethanal and hydrogen cyanide

d)

ethanoic acid and sodium hydroxide

17.

For this question refer to the reaction scheme shown. Which one of the following statements is not correct?

a)

Reaction of W with sodium cyanide followed by hydrolysis of the resulting product gives propanoic acid.

b)

Mild oxidation of Z produces a compound that reacts with Tollens’ reagent, forming a silver mirror.

c)

Z reacts with ethanoic acid to produce the ester propyl ethanoate.

d)

W undergoes addition polymerisation to form poly(propene).

18.

Look at the image. Isomers of the ester HCOOCH2CH2CH3, include

(i) ethyl ethanoate

(ii) methyl propanoate

(iii) butanoic acid

(iv) butyl methanoatea

a)

A

b)

B

c)

C

d)

D

19.

How many structural isomers with the molecular formula C5H10O react with Tollens’ reagent?

a)

3

b)

4

c)

5

d)

6

20.

Which one of the following conversions does not represent a reduction?

a)

propene → propane

b)

propanal → propan-l-ol

c)

propanal → propanoic acid

d)

propanone → propane

21.

Which one of the following reactions involves nucleophilic addition?

a)

CH3CH = CH2 + HBr → CH3CHBrCH3

b)

CH3CH2CH3 + Cl2 → CH3CHClCH3 + HCl

c)

CH3CH2CH2Br + NaOH → CH3CH2CH2OH + NaBr

d)

CH3CH2CHO + HCN → CH3CH2CH(OH)CN

22.

Which one of the following isomers is not oxidised under mild reaction conditions?

a)

(CH3)2CHCH(OH)COCH3

b)

(CH3)2C(OH)CH2COCH3

c)

(CH3)2CHCH(OH)CH2CHO

d)

(CH3)2C(OH)CH2CH2CHO

23.

Propanone can be reduced to form an alcohol. A functional group isomer of the alcohol formed is ...

a)

CH3CH2CH2OH

b)

CH3CH2CHO

c)

CH3OCH2CH3

d)

CH3COCH3

24.

Which alcohol could not be produced by the reduction of an aldehyde or a ketone?

a)

2,2-dimethylpropan-1-ol

b)

2-methylbutan-2-ol

c)

3-methylbutan-2-ol

d)

pentan-3-ol

25.

Which one of the following reactions will produce an organic compound that has optical isomers?

a)

dehydration of butan-2-ol by heating with concentrated sulphuric acid

b)

reduction of pentan-3-one by warming with NaBH4

c)

addition of Br2 to 3-bromopropene

d)

reduction of 2,3-dimethylpent-2-ene with H2 in the presence of a nickel catalyst