A chemist was investigating the reactions of benzene, phenol and cyclohexene with
bromine. She found that they all reacted with bromine but under different conditions.
(a)
The chemist found that when benzene reacts with bromine, a halogen carrier is
required as a catalyst.
Write an equation for this reaction.
You do not need to show the halogen carrier in your equation.
[1]
(b)
The chemist also found that when phenol or cyclohexene reacts with bromine, a
halogen carrier is not required.
(i)
[2]
(ii)
(iii)
2.
N
N
OH
H3C
compound A
Draw the displayed formula of the aromatic amine and of the diazonium ion.
State the reagents and conditions for each stage in the synthesis of compound A
from an aromatic amine.
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[Total 5 marks]
3.
State what the biochemist would see when hydroxyethanal reacts with
Tollens reagent.
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[1]
(ii)
[1]
(b)
[2]
(c)
(ii)
[4]
[Total 9 marks]
4.
COOH
H3C
H3C
OH
H
aspirin
paracetamol
reaction 2
reaction 3
Draw the structure of a compound that could react with ethanoic anhydride to form
aspirin.
[Total 1 mark]
5.
Complete the reactions by drawing structural formulae in each of the boxes provided.
Tollens reagent
(i)
CH3CHO
(ii)
C6H6
heat
[1]
(iii)
CH3CH2CH2Br
heat
[1]
HCl(aq)
(iv)
CH3COOCH2CH3
heat
+
[2]
(v)
OH
Br2
room temperature
[1]
(vi)
N
N+ Cl
OH
NaOH(aq) < 10 oC
[2]
[Total 8 marks]
6.
NaBH4
step 1
C
H
H
O
CH3C H2
CH3CH2
C
H
step 2
H
organic product
(i)
Add 'curly arrows' to the mechanism to show how the intermediate reacts with the
water molecule in step 2.
[2]
(ii)
(iii)
(iv)
Describe, in words, exactly what is happening to the electron pairs and bonds in
step 1 of the mechanism above.
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[3]
[Total 7 marks]
7.
Benzene reacts with chlorine in the presence of a halogen carrier, such as AlCl3.
(a)
(i)
[1]
(ii)
How does the halogen carrier allow the reaction to take place?
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[1]
(iii)
[4]
(iv)
(b)
In contrast to benzene, the reaction of an alkene with bromine does not need a
halogen carrier.
Compare the different reactivities of benzene and alkenes towards chlorine.
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[3]
[Total 10 marks]
8.
An unknown colourless liquid with molecular formula C4H8O was thought to be one of
butanal, but-3-en-1-ol, or butanone.
H
H
O
C
butanal
(a)
C
H
OH
H
H
but-3-en-1-ol
butanone
butanal only;
reagent .................................................................................................
observation ...........................................................................................
organic product .....................................................................................
[3]
10
(ii)
but-3-en-1-ol only.
reagent .................................................................................................
observation ...........................................................................................
type of reaction .....................................................................................
[3]
(b)
9.
The method below can be used to make phenylamine from nitrobenzene in the
laboratory.
3.69 g of nitrobenzene and 8 g of tin (an excess) were placed into a flask. The flask
was fitted with a reflux condenser. Concentrated hydrochloric acid was then added
dropwise to the flask.
The mixture was heated for 30 minutes to complete the reaction.
Once the mixture had cooled, concentrated sodium hydroxide solution was added until
the mixture was alkaline.
Purification gave a 72.1% yield of phenylamine.
11
(a)
NO2
[H]
HCl
NH3 + Cl
phenylammonium chloride
[2]
(ii)
(b)
When the sodium hydroxide was added, the phenylammonium chloride was
converted to phenylamine.
Write an equation for this reaction.
[2]
12
(c)
Calculate the mass of phenylamine that was produced from the 3.69 g of
nitrobenzene in this experiment. Give your answer to three significant figures.
Mr: nitrobenzene,123; phenylamine, 93.1
mass of phenylamine = . g
[4]
[Total 9 marks]
13
10.
In this question, one mark is available for the quality of spelling, punctuation and
grammar.
Describe with the aid of suitable diagrams the bonding and structure of a benzene
molecule.
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[6]
Quality of Written Communication [1]
[Total 7 marks]
14
11.
The demand for natural shampoos and detergents has led to the development of more
biodegradable detergents such as sorbitan monolaurate, which is made from plants.
OH
O
C11 H23
O
O
HO
OH
sorbitan monolaurate
(i)
Suggest a type of reaction that could break down sorbitan monolaurate when it is
washed into drains and rivers.
Explain your answer and state the type of organic products formed.
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[3]
(ii)
Suggest one other reason why detergents such as sorbitan monolaurate are
regarded as environmentally friendly.
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[1]
[Total 4 marks]
15
12.
OH
Br
Br
Br
OH
II
phenol
IV
III
OH
OH
NO2
N
N
(i)
On the diagram above, identify suitable reagents that could be used to carry out
reactions I, II and III.
[3]
(ii)
16
(iii)
Outline how you could carry out reaction IV in the laboratory starting from phenol
and a suitable aromatic amine.
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[5]
[Total 9 marks]
17
13.
In this question, one mark is available for the quality of spelling, punctuation and
grammar.
Phenol reacts much more readily with bromine than benzene does.
Explain why electrophiles, such as bromine, react much more readily with phenol
than with benzene.
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[7]
Quality of Written Communication [1]
[Total 8 marks]
18
14.
(i)
(ii)
Explain why this test gives a different result with aldehydes than it does
with ketones.
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...............................................................................................................
[1]
(b)
...............................................................................................................
[1]
(ii)
19
(c)
[1]
[Total 6 marks]
15.
(a)
O
Cl
C
H
Cl
O
Cl
Cl
H
H
[5]
20
(b)
The recommended adult dose of chloral hydrate as a sedative is 250 mg, three
times a day.
Calculate the mass of trichloroethanal you would need to react with water to
make one weeks supply of chloral hydrate for an adult, assuming a 60% yield.
Mr: chloral hydrate, 165.5; trichloroethanal, 147.5
mass of trichloroethanal = g
[3]
[Total 8 marks]
16.
Chloral hydrate is broken down in the body after several hours. One reaction is
oxidation to trichloroethanoic acid.
Complete the equation for this reaction below.
Cl3CCH(OH)2
[O]
[Total 1 mark]
17.
[2]
21
(b)
Outline how you could obtain a sample of ester D, starting with a named
carboxylic acid and a named alcohol.
Include any essential reaction conditions and write an equation for the reaction.
You do not need to include any details of the separation or purification of the
ester.
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[6]
(c)
22
18.
Draw the structure of the triglyceride made from linoleic acid, C17H31COOH, and
propane-1,2,3-triol. Show clearly all the bonds in the ester groups.
[2]
(ii)
19.
Explain why triglycerides are soluble in non-polar solvents and not in water.
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[Total 3 marks]
23
20.
H3 C
C
H
CH2
O
C
CH3
compound A
(a)
(i)
Apart from the benzene ring, name the two functional groups in
compound A.
.....................................................
.....................................................
[2]
(ii)
[1]
(iii)
24
(b)
(c)
If the food is cooked for a long time, naturally occurring acids catalyse the
hydrolysis of compound A.
Draw structures to show the two organic compounds formed by the acid
hydrolysis of compound A.
[2]
(d)
25
(ii)
21.
Phenol reacts readily with dilute nitric acid at room temperature in a nitration reaction to
produce a mixture of products as shown below.
OH
OH
dilute HNO3
OH
NO2
and
room temp
NO2
(a)
Suggest the structure of another organic product that is likely to be formed in the
nitration of phenol.
[1]
26
(b)
mass of 4-nitrophenol = g
[4]
27
(c)
In this question, one mark is available for the quality of spelling, punctuation and
grammar.
Compare the reagents and conditions for the nitration of phenol with those used
for the nitration of benzene.
State and explain the effect of the OH group on the reactivity of the benzene
ring in phenol.
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[7]
Quality of Written Communication [1]
[Total 13 marks]
28
22.
4-Nitrophenol can be converted into a range of useful organic chemicals. Draw the
structures of the organic products formed in the following reactions.
NaOH(aq)
Br2(aq)
OH
NO2
Sn(s)
conc.
HCl(aq)
CH3COCl(I)
[Total 4 marks]
23.
The reducing agent, NaBH4, is used widely in organic chemistry. One example is for
the reduction of diphenylethanedione, C14H10O2, shown below.
O
C
C
O
diphenylethanedione
29
(i)
Draw a displayed formula to show the structure of the organic product that would
be formed by reducing diphenylethanedione with excess NaBH4.
[1]
(ii)
Complete and balance the equation for this reaction, using [H] to represent the
reducing agent.
C14H10O2
[1]
[Total 2 marks]
24.
30
25.
26.
(a)
In this question, one mark is available for the quality of use and organisation of
technical terms.
Bromine is used in organic chemistry to carry out a variety of electrophilic
reactions.
(i)
31
(ii)
Use your answer to (i) to explain why bromine reacts much more readily
with cyclohexene than it does with benzene.
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[7]
Quality of Written Communication [1]
32
(b)
(ii)
[1]
[Total 11 marks]
27.
[Total 2 marks]
33
28.
As a wine ages, some of the acids slowly react with ethanol in the wine to produce
esters.
(i)
Draw a displayed formula to show the structure of the ester formed when lactic
acid reacts with ethanol.
[1]
(ii)
Suggest what effect this process might have on the flavour of the wine. Explain
your reasoning.
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[1]
[Total 2 marks]
29.
Salicylic acid is used in the manufacture of aspirin tablets. In the UK around 3500
tonnes of salicylic acid are manufactured per year.
O
OH
C
HO
salicylic acid
(a)
34
(ii)
[1]
(b)
The phenoxide ion is then combined with carbon dioxide under high pressure to
form the salicylate ion.
O
CO2
OH
O
step 1
H
step 2
O
intermediate
(i)
Add partial charges + and to show the polarisation of the C=O bonds in
the carbon dioxide molecule above.
[1]
(ii)
35
(iii)
(c)
In the final stage of this process, the salicylate ion is acidified to give salicylic
acid.
Assuming an overall yield by mass of 45% for this three stage process, calculate
the mass of phenol that is needed to produce the annual UK output of
3500 tonnes of salicylic acid.
Mr of phenol = 94.0; 1 tonne = 106 g
36
30.
CH3
NH2
4-methylphenylamine
2,6-dimethylphenol
(i)
(ii)
Draw the structure of the organic compound formed in the ice-cold acidic mixture,
showing a displayed formula of the nitrogen-containing group.
[1]
(iii)
(iv)
37
(v)
[2]
[Total 6 marks]
31.
In this question, one mark is available for the quality of use and organisation of
scientific terms.
4-Methylphenylamine can be manufactured from benzene in three stages.
NH2
stage 1
stage 2
stage 3
CH3
benzene
4-methylphenylamine
38
39
32.
OH
geraniol
Mild oxidation of geraniol gives an aldehyde Y.
(i)
aldehyde Y
[2]
(ii)
[O]
[2]
[Total 4 marks]
33.
Reaction of geraniol with ethanoic acid can be used to make ester Z, which is used in
chewing gum and desserts.
(i)
40
(ii)
State the conditions needed to make ester Z from geraniol and ethanoic acid.
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[2]
(iii)
C9H15CH2OH
[3]
[Total 6 marks]
34.
(b)
State the conditions required for the nitration of benzene using nitric acid and
sulphuric acid.
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[2]
(c)
[2]
41
(d)
H2SO4
H2O
NO2+
HSO4
NO2
NO2
step 2
+
H
step 3
+
intermediate
HSO4
H2SO4
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[2]
(ii)
(iii)
42
(iv)
How does the mechanism show that the sulphuric acid is acting as a
catalyst?
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[1]
(e)
In this question, one mark is available for the quality of spelling, punctuation and
grammar.
The benzene ring and the ring in the intermediate formed after step 2 have
different structures shown below. Both structures have -bonds.
+
benzene ring
Deduce how many electrons are involved in the -bonding in each structure and
describe how their arrangements are different.
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[5]
Quality of Written Communication [1]
[Total 17 marks]
43
35.
Describe how you would prepare a sample of an azo dye in the laboratory from
an amine, a phenol and any other necessary reagents.
44
(b)
SO3Na+
(i)
E110
On the structure above, draw a circle around the functional group that
identifies this molecule as an azo dye.
[1]
(ii)
Deduce how many carbon and hydrogen atoms are in a molecule of E110.
..................... carbon atoms and ..................... hydrogen atoms.
[2]
(c)
45
(d)
In the boxes below, draw the structures of a phenol and an amine that could be
used to make E110 by the method in part (a).
Assume that the SO3Na+ groups do not change during the process.
phenol
amine
[2]
[Total 13 marks]
36.
Benzoic acid and phenylmethanol will react with each other in the presence of a
suitable catalyst.
(i)
(ii)
[2]
[Total 3 marks]
46
37.
(ii)
[H]
[1]
[Total 2 marks]
47
38.
In this question, one mark is available for spelling, punctuation and grammar.
Tollens reagent can be used to identify the aldehyde group in cinnamaldehyde.
Describe how you would make Tollens reagent and carry out this test in the
laboratory.
Explain what happens to both the Tollens reagent and the cinnamaldehyde in
this reaction. Identify the organic product.
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[7]
Quality of Written Communication. [1]
[Total 8 marks]
48
39.
H 2N
NH2
1,4-diaminobenzene
(a)
Explain what is meant by the term 1,4-diamino in the name of this compound.
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[2]
(b)
O2N
NO2
1,4-dinitrobenzene
(i)
H2N
NH2
1,4-diaminobenzene
(ii)
State reagents and conditions that could be used to carry out this reaction.
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[2]
49
(iii)
O2N
NO2 +
[H]
H2N
NH2 +
[2]
(c)
(ii)
[2]
50
(iii)
H 2N
hexane-1,6-diamine
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[3]
[Total 14 marks]
51