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3.3.8 Aldehydes and ketones (A-level only)

Total questions: 26

Worksheet time: 13mins

Name
Class
Date
1.

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

a)

3

b)

4

c)

5

d)

6

2.

Which pair of compounds does not form a racemic mixture when the compounds react?

a)
b)
c)
d)
3.

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

4.

Which compound forms a racemic mixture when reacted with KCN followed by dilute acid?

a)

HCHO

b)

CH3CHO

c)

CH3COCH3

d)

(CH3CH2)2CO

5.

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

a)

2-methylbutan-1-ol

b)

2-methylbutan-2-ol

c)

3-methylbutan-1-ol

d)

3-methylbutan-2-ol

6.

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

7.

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

8.

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

9.

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

10.

Which one of the following would not reduce an acidified aqueous solution of potassium dichromate(VI)?

a)

CH3COOH

b)

Zn

c)

CH3CHO

d)

Fe2+(aq)

11.

Which one of the following statements about but-2-enal, CH3CH=CHCHO, is not true?

a)

It has stereoisomers.

b)

It shows a strong absorption in the infra-red at about 1700 cm−1.

c)

It will turn an acidified solution of potassium dichromate(VI) green.

d)

It can be dehydrated by concentrated sulphuric acid.

12.

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)
b)
c)
d)
13.

Which one of the following can act as an oxidising agent but not as a reducing agent?

a)

CH3CHO

b)

Fe2+

c)

I

d)

MnO4-

14.

Certain chemical tests were performed on the pain-relief drug ibuprofen. The results of these tests are given in the table.


Which one of the following functional groups do these results suggest that ibuprofen contains?

a)
b)
c)
d)
15.

On reduction, a racemate can be formed by

a)

CH3CH2CH2CH2CHO

b)

CH3CH2CH2COCH3

c)

CH3CH2COCH2CH3

d)

CH3CH=CHCH2CHO

16.

How many structural isomers, which are aldehydes, have the molecular formula C5H10O?

a)

2

b)

3

c)

4

d)

5

17.

Which one of the following will undergo nucleophilic addition?

a)

hex-3-ene

b)

hexan-3-one

c)

3-bromohexane

d)

hexan-3-ol

18.

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

19.

In which of the following is a curly arrow used incorrectly?

a)
b)
c)
d)
20.

Which one of the following can react both by nucleophilic addition and by nucleophilic substitution?

a)
b)
c)
d)
21.

In which one of the following are the curly arrows not used correctly?

a)
b)
c)
d)
22.

CH2O is the empirical formula of

a)

methanol

b)

methyl methanoate

c)

ethane-1,2-diol

d)

butanal

23.

Which one of the following does not represent an oxidation?

a)

propene → propane

b)

propan-l-ol → propanal

c)

propan-l-ol → propanoic acid

d)

propanal → propanoic acid

24.

Which one of the following is not a suitable method for the preparation of ethanol?

a)

oxidation of ethane

b)

hydration of ethene

c)

reduction of ethanal

d)

hydrolysis of bromoethane

25.

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

26.

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