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Second Term Test 2020/2021

S5 CHEMISTRY

SECTION B : Question-Answer Book

INSTRUCTIONS
Name
(1) After the announcement of the start of the
examination, you should first write your Name, Class 5____
Class, Class Number, Block and Block Class
Number in the spaces provided on this cover. Number

(2) Refer to the general instructions on the cover Block X1 / X2 / X3

of the Question Paper for Section A. Block
Number
(3) This section consists of TWO parts, Parts I and
II.

(4) Answer ALL questions in both Parts I and II.

Write your answers in the spaces provided in Marks
this Question-Answer Book. Do not write in
the margins. Answers written in the margins Section A /36
will not be marked.
Section B / 44
(5) An asterisk (*) has been put next to the Total (A+B):
questions where one mark will be awarded for /80
effective communication.

(6) No extra time will be given to students for

writing your Name, Class, Class Number,
Block and Block Number in the spaces Parents’ signature :
provided on this cover after the ‘Time is up’
announcement.

-- 1 –
 PART I
Answer ALL questions. Write your answers in the spaces provided.
A Periodic Table is printed on page 12. Atomic numbers and relative atomic masses of elements can be
obtained from the Periodic Table.

1. The structures of compounds are shown below:

Compound Structure

OH

X H NH2 H H CH3
HO N
OH
O O

Y O

Z
HO
H

H
(a) Which one of W, X, Y or Z is a secondary alcohol ?

(1 mark)

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Answers written in the margins will not be marked.
1. (b) Label all chiral centre(s), if any, by using ‘*’ on the structure of Y below.

(c) Heating X under reflux in 2 M KOH(aq) can form an optically active organic compound P and an
optically inactive organic compound Q. Draw the respective structures of P and Q.

P:

Q:

(2 marks)
(d) Consider the following reagents :

Br2(aq) acidified K2Cr2O7(aq) NaHCO3(aq)

(i) Suggest which one of the reagents can be used to perform a chemical test, in order to
distinguish X from W, Y and Z.

(ii) State the observation in the test involved in (i). Explain your answer.

(3 marks)

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Answers written in the margins will not be marked.
2. The structural formula of cis-dimethyl fumarate is shown below:

(a) Write the structural formula of the trans isomer of the compound. (1 mark)

(b) State and explain which isomer (cis or trans) has higher melting point.

(3 marks)

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* 3. In a soapless detergent which has an active surfactant of trimethyl hexadecylammonium bromide.
With reference to the structure of trimethyl hexadecylammonium bromide below, explain why it
has cleansing properties.

CH3
N Br-
H3C CH3
(5 marks)

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Marker’s C
Use Only

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Answers written in the margins will not be marked.
4. Outline a synthetic route, with no more than three steps, to accomplish the following conversion. For
each step, give the reagent(s), reaction conditions (as appropriate) and structure of the organic
product.

O O O

H OH O

(3 marks)

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5. Aspirin is a pain-killer. Its structure is shown below :

(a) State one medical application of aspirin other than pain-killing.

(1 mark)

(b) Explain why a suspension of aspirin and water can become clear when sodium carbonate powder is
added.

(2 marks)

(c) Heating aspirin with excess dilute aqueous hydrochloric acid under reflux will give two organic
products.

(i) Draw the structures of these two organic products.

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5. (c) (ii) Explain why the conversion of aspirin to these two organic products can hardly reach 100%
even though the mixture of aspirin and dilute HCl(aq) is heated under reflux for a long time.

(3 marks)
(d) Naproxen is also a pain-killer. Its structure is shown below :

OH

O
O
There exists enantiomerism in ibuprofen. Draw the three-dimensional structures for the pair of
enantiomers.

(2 marks)

6. Explain why HO2C(CH2)4CO2H can form a polymer with H2N(CH2)6NH2, but CH3(CH2)4CO2H
cannot.

(2 marks)

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 Part II

Answer ALL questions. Write your answers in the spaces provided below.

7. Answer the following short questions :

(a) Suggest how Na2SO4(s) and Na2SO4 . 10H2O(s) can be distinguished.

(2 marks)
(b) Suggest a test to distinguish between calcium ions and copper(II) ions.

(1 mark)
(c) Suggest a chemical test for detecting chlorine gas.

(2 marks)
(d) An organic compound A reacts with 2,4-dinitrophenylhydrazine to form an orange-red solid B. The
structure of B is shown below :

H
N
N

O2N
NO2
Given that the molecular formula of A is C10H10O, draw the structure of A.

(1 mark)

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Answers written in the margins will not be marked.
8. X and Y are isomeric compounds with their structures shown below :

O O

O OH

X Y
The melting point of X is 40oC while that of Y is 115oC. Both of them are insoluble in water but
soluble in dichloromethane. When treated with dilute NaHCO3(aq), no reaction occurs for X but
reaction occurs for Y to form a soluble salt.

(a) You are provided with dilute NaHCO3(aq) and dilute H2SO4(aq). Outline an experimental procedure,
based on solvent extraction, to separate solid Y from a solution of X and Y in dichloromethane.

(4 marks)
(b) Suggest how you can identify that the solid obtained in (a) is pure compound Y.

(1 mark)

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9. Another sample of X is contaminated with a colourless organic compound. The sample is analysed by
thin-layer chromatography (TLC), and the result is shown below:

(a) Suggest ONE method that can be used to make the two spots on the chromatographic plate
become visible.

(1 mark)

(b) Given that Spot A corresponds to X, calculate the Rf of X.

(1 mark)

(c) Based on the TLC results, suggest ONE method to separate X from the contaminated sample.
Describe briefly.

(2 marks)

END OF SECTION B
END OF PAPER

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