Synthesis and stereoisomerism exam qs

Name..
1.

Chemists are currently developing renewable sources of organic chemicals to replace

diminishing crude oil reserves.
One process involves the conversion of plant material to 4-oxopentanoic acid. This can
then be converted to other useful organic compounds, including those shown below.
C O O H

4 -o x o p e n ta n o ic a c id

S O C l2

re a g e n t C
C O O H

O H

com pound D
hot
A l2O

com pound E
C 2H 5O H

O
C O O H

O
O

com pound F
( p o ly m e r p r o d u c tio n )

(a)

com pound G
( d ie s e l f u e l a d d it iv e )

Complete the scheme by filling in the boxes to:

(i)

identify reagent C
[1]

(ii)

state the name of compound D

[1]

(iii)

draw the structure of compound E.

[1]

Christ The King Sixth Form College

Synthesis and stereoisomerism exam qs

(b)

Compound F can be used to form a polymer.

(i)

Draw a short section of this polymer showing at least three repeat units.

[1]

(ii)

Draw a circle round one repeat unit on your structure.

[1]

(c)

Compound G can be added to diesel fuel to reduce the amount of soot formed
when the fuel burns.
(i)

Deduce the molecular formula of compound G.

...............................................................................................................
[1]

(ii)

Write a balanced equation for the complete combustion of compound G.

[2]

(iii)

Suggest how compound G reduces the amount of soot when the fuel burns.
...............................................................................................................
...............................................................................................................
[1]

Christ The King Sixth Form College

Synthesis and stereoisomerism exam qs

(d)

If compound G is accidentally spilt, it is broken down rapidly in the environment

by reactions such as alkaline hydrolysis.
(i)

State the reagents and conditions that would normally be used for alkaline
hydrolysis in the laboratory.
...............................................................................................................
...............................................................................................................
[2]

(ii)

Explain why compound G is able to be hydrolysed.

...............................................................................................................
...............................................................................................................
[1]
[Total 12 marks]

2.

Compound A, shown below, contributes to the smell and taste of black tea and is a
component in jasmine oil.
O

(i)

Deduce the molecular formula of compound A.

.............................................................
[1]

Christ The King Sixth Form College

Synthesis and stereoisomerism exam qs

(ii)

Compound A contains several functional groups.

Identify, by name, the functional groups in compound A.
........................................................................................................................
........................................................................................................................
........................................................................................................................
[3]

(iii)

Compound A is a stereoisomer.
On the structure above,

mark each feature responsible for stereoisomerism with an asterisk, *,

label each feature with the type of stereoisomerism.

[2]

(iv)

Outline two important factors that pharmaceutical companies need to consider

when manufacturing chiral compounds for use as medicines.
........................................................................................................................
........................................................................................................................
..........................................................................................................................
[2]
[Total 8 marks]

Christ The King Sixth Form College