WM

End of module test

Whats in a Medicine? end of module test

60 marks (1 hour)

A copy of the Data Sheets is required for this test.

1

An ester D is used in food avourings. The formula of D is CH3COOCH3.

a

Draw the full structural formula and give the systematic name for ester D.

[2]

Ester D can be made in the laboratory by the reaction of ethanoyl chloride with alcohol E.
i Give the full structural formula of ethanoyl chloride.
ii Suggest the name of the alcohol E that reacts with ethanoyl chloride to make ester D.

[1]
[1]

Ester D can also be made by reacting alcohol E with carboxylic acid F, CH3COOH. The reaction is carried out by heating
under reux.
i Give the systematic name of carboxylic acid F.
[1]
ii Name the other reagent that would be needed to obtain a reasonable yield of ester D by this method.
[1]
iii Explain what is meant by heating under reux and give one reason why it is necessary in this reaction.
[3]

Carboxylic acid F, CH3COOH, can be made by the oxidation of another alcohol, G.

i Give the formula of alcohol G.
ii Give the reagents and conditions necessary to convert alcohol G into carboxylic acid F.
iii Classify alcohol G as a primary, secondary or tertiary alcohol. Explain your answer.
iv Give the conditions necessary to convert alcohol G into an aldehyde H.
v Give the systematic name of aldehyde H and draw its full structural formula.
vi Aldehyde H reacts with hydrogen cyanide. Give the structure of the compound formed.

[1]
[3]
[2]
[2]
[2]
[1]
[TOTAL: 20 MARKS]

Cannabis resin contains compounds called cannabinoids. Two compounds contained in fresh cannabis resin are shown below.
C5H11

HO
H3C

C5H11

HO
H3C

COOH
O
H3C

CH3
A

H3C

CH3
B

Describe, using diagrams, how you would carry out thin-layer chromatography to demonstrate that cannabis resin contains a
mixture of compounds.
[5]

Samples of compounds A and B are isolated from the resin and puried. Various chemical tests are carried out on the
compounds.
i Both compounds A and B contain an OH group attached to a benzene ring. Give the name of this functional group.
ii Describe a test (with the expected result) that would show the presence of this functional group.

[1]
[2]

Compound B will react with aqueous sodium hydroxide.

i Give the formula of the functional group in compound B that causes this reaction.
ii What would be observed if compound B were added to aqueous sodium carbonate? Explain your answer.

[1]
[2]

Compound A contains a carboxylic acid group, COOH.

i Write the equation for the reaction of the carboxylic acid group with a hydroxide ion.
ii Use your equation to explain why the hydroxide ion can be described as a base.

[1]
[1]

Compounds A and B have different relative molecular masses.

i Give the name of the spectroscopic technique that could be used to show this.
ii Explain how the spectra of the two compounds would be used to show this difference.

[1]
[1]

24

Compound A contains a C=O bond.

i Give the name of the spectroscopic technique that could be used to show the presence of a C=O bond in compound A. [1]
ii Explain how the spectrum would show the presence of a C=O bond.
[1]
iii What happens to the C=O bond when it absorbs infrared radiation?
[2]
[TOTAL: 19 MARKS]
Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.
This document may have been altered from the original.

WM

End of module test

3

In 1936 the compound pethidine, a powerful painkiller, was synthesised by chance. The general structure of pethidine is shown
below.
&+
1

O
&+

C O
pethidine

CH

Two peaks in the mass spectrum of pethidine occur at masses of 15 and 77. Suggest the formulae of the ions giving rise to
these two peaks.
[3]

When pethidine is hydrolysed with aqueous acid, ethanol is formed.

i The infrared spectrum of ethanol is given below. Explain how it shows the presence of an alcohol.
ii What feature of the infrared spectrum would be used to conrm that the spectrum is specically that of ethanol?

[2]
[1]

100

Transmittance (%)

80
60
40
20

4600

3800

3000

2200

1800
1400
Wavenumber/cm
1

1000

800

600

400

The infrared absorption spectrum of ethanol.

When pethidine was rst discovered, clinical trials were carried out on the medicine. Give three questions that these trials
would answer about the potential of pethidine as a medicine.
[3]

Having discovered a medicine which is effective, scientists then prepare a large number of related compounds.
i Explain why they do this.
ii Name the technique that scientists use to prepare large numbers of related compounds. Explain how the use of this
technique helps the development of new medicines.

e

Esters like pethidine can be synthesised by the reactions of carboxylic acids with alcohols.
For example:
2#//(#2H5OH 2#//#2H5 + H2O
i Calculate the atom economyOFTHISREACTIONGIVENTHAT2HASAMOLARMASSOF
ii Explain the importance of seeking methods of making medicines that have high atom economies.
Some types of reaction are listed below:
addition
condensation
elimination
i Which one of these terms describes the reaction in part e?
ii Which one of these types of reaction has the highest atom economy? Explain why.
iii Write the equation for an elimination reaction of ethanol. Name the organic product of the reaction.

Salters Advanced Chemistry, Pearson Education Ltd 2009. University of York.

This document may have been altered from the original.

[1]
[2]

;=
[1]

[1]
[2]
[2]
[TOTAL: 21 MARKS]

25