A2 LEVEL CHEMISTRY

4.2.1 AMINO ACIDS AND CHIRALITY

4.2.2 POLYESTERS AND POLYAMIDS
4.2.3 SYNTHESIS

ASSESSED HOMEWORK

Answer all questions

Max 107 marks

Name

..

Mark

../107

Paddington Academy

....%

Grade

1.

Compound A, shown below, is an amino acid that is being used in the development of
a new anti-inflammatory drug.

H 2N

C H

O
C

O H

com pound A
(a)

(i)

Explain why this molecule is described as an amino acid.

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

(ii)

State the general formula of an -amino acid.

Explain whether or not compound A fits this general formula.

...............................................................................................................
...............................................................................................................
[2]

(b)

Compound A exists as a zwitterion in aqueous solution.

(i)

Draw the structure of this zwitterion.

[1]

(ii)

Show how the structure of the zwitterion would change if the solution was
acidified with dilute hydrochloric acid.

[1]
Paddington Academy

(c)

The anti-inflammatory drug is made by combining compound A with compound

B, shown below. R represents a side chain.
H
R

C
H

O
C
O H

com pound B
Show the structure of the anti-inflammatory drug formed from compound A and
compound B.

[2]
[Total 7 marks]

Paddington Academy

2.

Amino acids can act as monomers in the formation of polypeptides and proteins. The
structures below show three amino acids, glycine, phenylalanine and proline.
H
H 2N

C
H

H
C O O H

H 2N

C
C H
C 6H

g ly c in e

H
C O O H

H N

H 2C

C H
C
H

p h e n y la la n in e

C O O H
2

p r o lin e

Glycine, phenylalanine and proline can react together to form a mixture of tripeptides.
(i)

Draw the structure of the tripeptide formed in the order glycine, phenylalanine
and proline.

[3]

(ii)

How many different tripetides could have been formed containing glycine,
phenylalanine and proline?
........................................................................................................................
[1]

(iii)

The mixture of tripeptides can be analysed by using gas chromatography,

coupled with mass spectrometry.
Summarise how each method contributes to the analysis.
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
[3]
[Total 7 marks]

Paddington Academy

3.

Compound A is currently being tested as a possible anti-allergic drug.

O

O H
C

H
N
H

CH

CH

H HC

C
H

O H

C
O

com pound A
Compound A can be hydrolysed to form three organic products.
(i)

Name a suitable reagent and conditions for the hydrolysis of compound A.

........................................................................................................................
........................................................................................................................
[2]

(ii)

The three organic products all belong to the same class of compound. State the
general name for this class of organic compound.
........................................................................................................................
[1]

(iii)

Draw the structure of one of the organic products from the hydrolysis of A using
the reagent you have given in (a)(i) above.

[2]

(iv)

Explain what is meant by the term hydrolysis. Use this reaction to illustrate your
answer.
........................................................................................................................
........................................................................................................................
........................................................................................................................
[2]
[Total 7 marks]

Paddington Academy

4.

In this question, one mark is available for the quality of the use and organisation of
scientific terms.
In all living organisms a large variety of polypeptides and proteins are formed naturally
from -amino acids.
State the general formula of an -amino acid and use it to describe how amino acids
can be combined to give a variety of polypeptides and proteins.

.................................................................................................................................
.................................................................................................................................
.................................................................................................................................
.................................................................................................................................
.................................................................................................................................
.................................................................................................................................
.................................................................................................................................
.................................................................................................................................
.................................................................................................................................
.................................................................................................................................
[6]
Quality of Written Communication [1]
[Total 7 marks]

Paddington Academy

5.

Some of the -amino acids found in human sweat are shown in the table below.

(i)

-amino acid

R group

glycine

leucine

CH2CH(CH3)2

isoleucine

CH(CH3)CH2CH3

alanine

CH3

valine

CH(CH3)2

lysine

(CH2)4NH2

glutamic acid

(CH2)2COOH

State the general formula of an -amino acid.

[1]

(ii)

There are four stereoisomers of isoleucine.

One of the stereoisomers is shown below.
H
HO O C

NH
C
C

H 3C

C H 2C H

H
Draw 3D diagrams for the other three stereoisomers of isoleucine.

[3]
[Total 4 marks]
Paddington Academy

6.

Glutamic acid and glycine are both -amino acids that occur widely in living organisms.
Their structures are shown below.

H
H 2N

H 2N

C O O H

CH

CH

C O O H

C O O H
g lu ta m ic a c id
(a)

(i)

g ly c in e

State the general formula for an -amino acid.

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

(ii)

Explain how glutamic acid and glycine both fit the general formula given in
part (i)
...............................................................................................................
...............................................................................................................
...............................................................................................................
[2]

(b)

Amino acids react with both acids and alkalis.

Draw structures below to show how the glutamic acid molecule is changed in the
presence of excess acid and alkali.
H
H 2N

excess
H C l( a q )

C O O H

C H

C H

excess
N a O H (a q )

C O O H
g lu ta m ic a c id

[5]
Paddington Academy

(c)

In this question, one mark is available for the quality of use and organisation of
scientific terms.
Glutamic acid exists as two optical isomers, but glycine does not.
Explain what structural feature causes optical isomerism in organic molecules.
Include appropriate diagrams and use these two amino acids to illustrate your
answer.
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
[7]
Quality of Written Communication [1]
[Total 16 marks]

Paddington Academy

7.

But-2-enal, CH3CH=CHCHO, is a pale yellow, flammable liquid with an irritating odour.

But-2-enal exists as two stereoisomers.
Draw skeletal formulae to show the structure of the two stereoisomers of but-2-enal.

[Total 2 marks]

Paddington Academy

10

8.

Cinnamaldehyde is the compound that gives cinnamon its distinctive flavour.

H
C

H
C

H
c in n a m a ld e h y d e
(a)

Draw the skeletal formula of cinnamaldehyde.

[1]

(b)

Cinnamaldehyde shows cis-trans isomerism.

(i)

Explain how cis-trans isomerism arises in cinnamaldehyde.

...............................................................................................................
...............................................................................................................
...............................................................................................................
...............................................................................................................
[2]

(ii)

State and explain whether cinnamaldehyde is a cis or a trans isomer.

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

(iii)

Draw a skeletal or displayed formula to show the structure of the other cistrans isomer of cinnamaldehyde.

[1]
[Total 5 marks]

Paddington Academy

11

9.

Synthetic polyamides, such as nylon, contain the same link as polypeptides. Nylon is
the general name for a family of polyamides.
A short section of a nylon polymer is shown below.

O
C

H
(C H 2)8

O
(C H 2)6

H
(C H 2)8

(C H 2)6

Draw the structures of two monomers that could be used to make this nylon.

[Total 2 marks]

10.

Nylon is sometimes used for electrical insulation. However, if there is a risk of high

temperatures then a polymer such as Nomex , with a higher melting point, is used.

The repeat unit of Nomex is shown below.

(i)

Draw the structures of two monomers that could be used to form Nomex .

[2]

(ii)

Suggest a reason why the melting point of Nomex is higher than that of nylon.
........................................................................................................................
........................................................................................................................
........................................................................................................................
[1]

Paddington Academy

12

[Total 3 marks]

11.

Poly(phenylethene) is one of the most versatile and successful polymers.

The 3-D skeletal formula of a section of atactic poly(phenylethene) is shown in the
diagram below.

(i)

State the type of polymerisation used to make poly(phenylethene).

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

(ii)

Draw a skeletal or displayed formula to show the monomer used to make

poly(phenylethene).

[1]

(iii)

Outline how the polymer is formed from the monomer molecules. (You do not
need to give any details of the catalyst or conditions involved.)

........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
[2]
[Total 4 marks]

Paddington Academy

13

12.

The fibres used in carpets are made from synthetic or natural polymers such as
TM
nylon-6,6, Orlon and wool.
(a)

Complete the table below.

nylo-6,6

monomer(s)

Orlon

TM

(C H 2)4

CO H O H

(C H 2)6 H N H

22

repeat unit of
the polymer

CN

type of
polymerisation
[4]

(b)

Nylon-6,6 can be made from its monomers in the laboratory in two stages as
shown below.
O
C

O
(C H 2)4

CO H O H

s ta g e 1
O
l

O
(C H 2)4

CC

Cl

( C H 2 ) N6 H N H

22

s ta g e 2
n y lo n - 6 ,6
Deduce the inorganic product that is also formed in stage 2.
...............................................................................................................
[1]

Paddington Academy

14

(c)

Industrially, nylon-6,6 is not manufactured by the method in (b). Instead, the two
monomers are mixed directly at room temperature to give a salt. This salt is then
heated to convert it to nylon-6.6.
Suggest the structures of the two ions present in this salt.

[2]

(d)

Wool is a protein. It is a natural polymer made by the same type of polymerisation

as nylon-6,6.
A section of the polymer chain in a protein is shown below.

CH

H 2C

CH

O H
(i)

How many monomer units does this section contain?

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

(ii)

Draw the structure of one of the monomer molecules that was used to form
this section.

[1]

(iii)

State three ways in which the monomer units of a protein differ from those
of nylon-6,6.
...............................................................................................................
...............................................................................................................
...............................................................................................................
...............................................................................................................
...............................................................................................................
[3]
[Total 12 marks]

Paddington Academy

15

13.

Aspirin and paracetamol are commonly available painkillers.

O

C O O H
H 3C

H 3C

O H

H
a s p ir in

p a ra c e ta m o l

Aspirin and paracetamol can be prepared using ethanoic anhydride, (CH3CO)2O.

Ethanoic anhydride can react with 4-aminophenol to produce paracetamol.
(i)

Write an equation, showing structural formulae, for this formation of paracetamol.

[2]

(ii)

An impurity with molecular formula C10H11NO3 is also formed.

Draw the structure of this impurity.

[1]

(iii)

Explain why it is necessary for pharmaceutical companies to ensure that drugs

and medicines are pure.
.........................................................................................................................
.........................................................................................................................
.........................................................................................................................
[1]
[Total 4 marks]

Paddington Academy

16

14.

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]

(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]

Paddington Academy

17

15.

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]

Paddington Academy

18

(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]

(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 11 marks]

Paddington Academy

19

16.

Compound A is currently being tested as a possible anti-allergic drug.

O

O H
C

H
N
H

CH

CH

H HC

C
H

O H

C
O

com pound A
Compound A can exist as a number of stereoisomers, but only one of them is
pharmacologically active as the anti-allergic drug.
(i)

Explain what causes stereoisomerism in compounds such as A.

........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
[3]

(ii)

Explain why there are four different stereoisomers of compound A.

........................................................................................................................
........................................................................................................................
........................................................................................................................
[2]

(iii)

Suggest how a drug company could synthesise compound A so that the drug
contains only the pharmacologically active stereoisomer.
........................................................................................................................
........................................................................................................................
[1]

Paddington Academy

20

(iv)

Sometimes it is difficult to manufacture a drug containing only the one

pharmacologically active stereoisomer.
Describe two possible disadvantages of producing a drug containing a mixture of
several stereoisomers.
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
........................................................................................................................
[2]
[Total 8 marks]

Paddington Academy

21