A2 LEVEL CHEMISTRY

4.1.2 CARBONYL COMPOUNDS

4.1.3 CARBOXYLIC ACIDS AND ESTERS
ASSESSED HOMEWORK
Answer all questions
Max 47 marks

Name

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Mark

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Grade

1.

Explain why triglycerides are soluble in non-polar solvents and not in water.
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[Total 3 marks]

2.

Reaction of geraniol with ethanoic acid can be used to make ester Z, which is used in
chewing gum and desserts.
(i)

Suggest why esters are used in the manufacture of foods.

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[1]

(ii)

State the conditions needed to make ester Z from geraniol and ethanoic acid.
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[2]

(iii)

Complete the equation for the formation of ester Z.

+ C9H15CH2OH

[3]
[Total 6 marks]

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3.

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

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4.

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.
O H
O

11

23

O
H O

O H
s o r b ita n m o n o la u r a te

(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]

5.

Complete the reactions by drawing structural formulae in each of the boxes provided.
T o lle n s r e a g e n t

(i)

CH3CHO

( a m m o n ia c a l A g N O 3 ) / h e a t
[1]

c o n c . H 2S O
(ii)

C6H6

and conc. H N O

heat
[1]

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H C l( a q )

(iii)

CH3COOCH2CH3

heat

[2]

(iv)
O H
B r2
ro o m te m p e ra tu re

[1]
[Total 5 marks]

6.

Propanal, CH3CH2CHO, can be used in the synthesis of organic compounds.

CH3CH2CHO reacts with NaBH4 in a nucleophilic addition reaction. The nucleophile

can be represented as a hydride ion, H . A mechanism for the reaction is shown below.
H +
+
H
O

O
C H 3C H

NaBH4
s te p 1

H
H

(i)

C H 3C H

s te p 2
H

o r g a n ic p r o d u c t

Add 'curly arrows' to the mechanism to show how the intermediate reacts with the
water molecule in step 2.
[2]

(ii)

Draw the structure of the organic product in the box above.

[1]

(iii)

What is meant by the term nucleophile?

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[1]

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(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.

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]

8.

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

(a)

(i)

Describe a simple chemical test that would show that but-2-enal is an

aldehyde.
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[2]

(ii)

Explain why this test gives a different result with aldehydes than it does with
ketones.
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[1]

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(b)

But-2-enal also reacts with sodium borohydride, NaBH4.

(i)

Identify the organic compound formed in this reaction.

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[1]

(ii)

State the type of chemical reaction occurring.

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[1]

(c)

Precautions must be taken to prevent but-2-enal catching fire.

Construct a balanced equation for the complete combustion of but-2-enal,
C4H6O.

[1]
[Total 6 marks]

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9.
(a)
The reaction of trichloroethanal with water is a nucleophilic addition
reaction. It can be catalysed by small amounts of hydroxide ions, OH.
Complete the diagram below to suggest a mechanism for this reaction. Show all
the relevant dipoles and curly arrows.
H
C l
C l

Cl

C
H

C l

Cl

Cl

O
H

[5]

(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]

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