A LEVEL CHEMISTRY

TOPIC 16 – ALDEHYDES, KETONES AND OPTICAL ISOMERISM

TEST

Answer all questions

Max 50 marks

Name

……………………………………………………………..

Mark ……../50 ……....% Grade ………

 SECTION A

1. (a) (i) Give a suitable reagent and state the necessary conditions for the conversion of propan-
2-ol into propanone. Name the type of reaction.

Reagent ..............................................................................................

Conditions ...........................................................................................

Type of reaction ...................................................................................

(ii) Propanone can be converted back into propan-2-ol. Give a suitable reagent and write
an equation for this reaction.
(Use [H] to represent the reagent in your equation.)

Reagent ...............................................................................................

Equation

.............................................................................................................
(5)

(b) Propanal is an isomer of propanone.

(i) Draw the structure of propanal.

(ii) A chemical test can be used to distinguish between separate samples of propanone
and propanal. Give a suitable reagent for the test and describe what you would observe
with propanone and with propanal.

Test reagent .........................................................................................

Observation with propanone ................................................................

Observation with propanone ................................................................

(4)
(Total 9 marks)
2. Consider the sequence of reactions below.

(a) Name and outline a mechanism for Reaction 1.

Name of mechanism ....................................................................................................

Mechanism

(5)

(b) Name compound Q

.............................................................................................................
(1)

(c) Draw the structure of the main organic product formed in each case when R reacts
separately with the following substances:

(ii) acidified potassium dichromate(VI);

(iii) concentrated sulphuric acid in an elimination reaction.

(2)
(Total 8 marks)
3. The reducing agent in the following conversion is NaBH 4

(i) Name and outline a mechanism for the reaction.

Name of mechanism ............................................................................

Mechanism

(5)

(ii) By considering the mechanism of this reaction, explain why the product formed is
optically inactive.

...............................................................................................................

...............................................................................................................

...............................................................................................................

...............................................................................................................

...............................................................................................................

...............................................................................................................

...............................................................................................................

...............................................................................................................
(3)
(Total 8 marks)
4. (a) P, Q and R have the molecular formula C H 6 12

All three are branched-chain molecules and none is cyclic.

P can represent a pair of optical isomers.
Q can represent a pair of geometrical isomers.
R can represent another pair of geometrical isomers different from Q.

Draw one possible structure for one of the isomers of each of P, Q and R.

Structure of P

Structure of Q

Structure of R

(3)

(b) Butanone reacts with reagent S to form compound T which exists as a racemic mixture.
Dehydration of T forms U, C H N, which can represent a pair of geometrical isomers.
5 7

(i) State the meaning of the term racemic mixture and suggest why such a mixture is
formed in this reaction.

Racemic mixture .................................................................................

.............................................................................................................

Explanation..........................................................................................

.............................................................................................................

.............................................................................................................

(ii) Identify reagent S, and draw a structural formula for each of T and U.

Reagent S ...........................................................................................

Compound T

Compound U

(6)
(Total 9 marks)
5. Compounds C and D, shown below, are isomers of C H O 5 10

C D

(a) Name compound C.

......................................................................................................................
(1)

(b) Use Table 2 on the Data Sheet to help you to answer this question.

(i) Suggest the wavenumber of an absorption which is present in the infra-red spectrum of
C but not in that of D.

.............................................................................................................

(ii) Suggest the wavenumber of an absorption which is present in the infra-red spectrum of
D but not in that of C.

.............................................................................................................
(2)

(c) Identify a reagent that you could use to distinguish between C and D. For each of C and D,
state what you would observe when the compound is treated with this reagent.

Reagent .......................................................................................................

Observation with C .......................................................................................

Observation with D .......................................................................................

(3)

(d) Compound E, CH CH CH CH CHO, is also an isomer of C H O

3 2 2 2 5 10

Identify a reagent which will react with E but not with C or D. State what you would observe
when E is treated with this reagent.

Reagent .......................................................................................................

Observation with E .......................................................................................

(2)
(Total 8 marks)

SECTION B

6. 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

(Total 1 mark)

7. 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
(Total 1 mark)

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

D
(Total 1 mark)
9. 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
(Total 1 mark)

10. Which one of the following will undergo nucleophilic addition?

A hex-3-ene

B hexan-3-one

C 3-bromohexane

D hexan-3-ol
(Total 1 mark)

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

A 2

B 3

C 4

D 5
(Total 1 mark)

12. On reduction, a racemate can be formed by

A CH3CH2CH2CH2CHO

B CH3CH2CH2COCH3

C CH3CH2COCH2CH3

D CH3CH=CHCH2CHO
(Total 1 mark)
13. 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?

D
(Total 1 mark)