962/3 STPM

Name : ............................................................ Class : ............................

TRIAL EXAMINATION
THIRD TERM OF STPM 2016

CHEMISTRY (KIMIA)
PAPER 3 (KERTAS 3)
One and a half hours (Satu jam setengah)

For examiner’s use

Instructions to candidates:

DO NOT OPEN THIS QUESTION PAPER UNTIL A

YOU ARE TOLD TO DO SO.

Answer all questions in Section A. Marks will not be B 16

deducted for wrong answers. For each question, four
suggested answers are given. Choose the correct B17
answer and circle the answer.

Answer all questions in Section B. Write your answers C 18

in the spaces provided.

Answer any two questions in Section C. All essen

essential C 19
working should be shown. For numerical answers,
unit should be quoted wherever appropriate. Begin
C 20
each answer on a fresh sheet of paper and arrange
your answers in numerical order.
Total

Answers of section A :

1. ,,,,,,,,,,,,,,,, 2.  3. 4. 5. .

6. ,,,,,,,,,,,,,,,, 7.  8. 9. 10. .

11. ,,,,,,,,,,,,,,,, 12.  13. 14. 15. .

 Section A.
Answer all questions
1. Use your knowledge of intermolecular forces to predict the compound with the highest boiling
temperature.
A 1-iodobutane B 1-chlorobutane
C 2-methyl-2-iodopropane D 2-methyl-2-chloropropane

2. Which molecule could not be obtained from the cracking of a molecule of nonane,
CH3(CH2)7CH3?
A CH2=CHCH=CH2 B CH3CH2CH2CH2CH3
C CH3CH2CH2CH2CH2CH=CH2 D (CH3CH2CH2)3CH

3. In the presence of ultraviolet light, ethane and chlorine react to give a mixture of products.
Which compound could be present in the mixture of products?
A CH3Cl B CH3CH2CH2Cl
C CH3CH2CH2CH3 D CH3CH2CH2CH2CH3

4. The free radical substitution reaction between methane and chlorine involves initiation,
propagation and termination stages. Which row is correct?

5. One reaction in the Krebs cycle, in which energy is released to the human body, is the
conversion of fumaric acid into malic acid.
HO2CCH=CHCO2H HO2CCH(OH)CH2CO2H
fumaric acid malic acid
Which reagent(s) could achieve this conversion in the laboratory?
A acidified KMnO4(aq) B Br2(aq) followed by hot NaOH(aq)
C H2O(l) with Pt catalyst D H2O(g) with H2SO4

6 Compound X produces a carboxylic acid when heated under reflux with acidified potassium
dichromate(VI). Compound X has no reaction with sodium metal.
What could be the identity of compound X?
A propanal B propanone C propan-1-ol D propan-2-ol

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7. Most alcohols can be dehydrated to give alkenes.
Which alcohol can be dehydrated to give three different isomeric alkenes?

A CH3(CH2)3CH2OH B CH3(CH2)2CH(OH)CH3
C CH3CH2CH(OH)CH2CH3 D CH3C(CH3)2CH2OH

8. Propane-1,2,3-triol
triol is the raw material for many important industrial chemical processes.

Which statements about propane-1,2,3-triol

propane are correct?
1 It reacts with carboxylic acids to form compounds containing up to three ester groups.
2 It can be oxidised to form compounds with aldehyde and ketone functional groups.
3 It can be oxidised to form compounds with up to three carboxylic acid groups.

A 3 only B 1 and 2 C 1 and 3 D 1, 2 and 3

9. Hydrogen cyanide, HCN, reacts with propanal, CH3CH2CHO, in the presence of

potassium cyanide, KCN.
The first stage of the mechanism of this reaction is
A the lone pair of electrons on carbon in CN– attacking Cб+ of propanal.
B the lone pair of electrons on nitrogen in CN– attacking C б+ of propanal.
C the lone pair of electrons on oxygen in propanal attacking C б+ of HCN.
D the lone pair of electrons on oxygen in propanal attacking H б+ in HCN.

10. Hept-4-enal
enal is present in cow’s milk.
CH3CH2CH=CHCH2CH2CHO (hept-4-enal)
Which row correctly shows the product formed when hept-4-enal
hept enal is treated with the given
reducing agent?

3
11. When hydrolysed with dilute sulfuric acid, which compounds produce propanoic acid?

1 CH3CH2CO2CH3 2 CH3CH2CH2CN 3 CH3CH2CH2Cl

A 1 only B 1 and 2 C 1 and 3 D 1, 2 and 3

12. Which of the following statements about ethanoyl chloride is NOT correct?
A It reacts with an amine to make an amide.
B It reacts with an alcohol to make an ester.
C It reacts with ammonia to make an amine.
D It reacts with water to make an organic acid.

13. The compound cetyl palmitate, C15H31CO2C16H33, is a waxy solid.

When cetyl palmitate is heated under reflux with an excess of aqueous sodium hydroxide, which
products will be formed?

A C15H31ONa and C16H33CO2Na B C15H31CO2Na and C16H33ONa

C C15H31CO2Na and C16H33OH D C15H31OH and C16H33CO2Na

14. Diesters can be made from diacids such as propane

propane-1,3-dioic
dioic acid, HO2CCH2CO2H.
Which combination of reactants would form the diester CH3CH2OCOCH2CH2CO2CH2CH3?

A ethanedioic acid and propan-1-ol

propan
B butane-1,4-dioic
dioic acid and ethanol
C ethanedioic acid, ethanol and butan-1-ol
butan
D propane-1,3-dioic
dioic acid, ethanol and propan
propan-1-ol

15. The naturally-occurring

occurring molecule shown below can be made by the addition of four identical
monomer molecules.

What could be the structural formula of the monomer?

A CH3CH2CH2CH=CH2 B CH3CH=CHCH=CH2
C CH2=C(CH3)CH2CH3 D CH2=C(CH3)CH=CH2

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 Section B [15 marks]
Answer all questions in this section

16 The following four isomeric esters with the molecular formula C7H14O2 are used as artificial
flavours in drinks and sweets to give a pear, banana or plum taste to foodstuffs.

A: CH3COO(CH2)4CH3 B : CH3COOCH2CH(CH3)CH2CH3

C : CH3COOCH2CH2 CH(CH3)2 D : CH3COOCH(CH3) CH2CH2CH3

(a) In each of the spaces below, write one or more of the letters A-D,, as appropriate. [3]
(i) Which of these compounds can exist as optical isomers?

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(ii) On hydrolysis, which of these compounds produce(s) a secondary alcohol?

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.............................................................................................................................................

(b) The hydrolysis of all these compounds produces ethanoic acid, CH3CO2H, as one of the
products. State the reagents and conditions needed for this hydrolysis. Write a balanced
equation for the hydrolysis reaction for ester C. [2]

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.............................................................................................................................
..............................................................................................................................

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(c) Name ester A. Give another isomer of A which is not an ester. [2]

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17 Organic chemists use a variety of methods to distinguish between compounds.

These methods include analytical and spectroscopic techniques.
The following compounds can be distinguished by observing what happens in test test-tube
reactions. For each pair, suggest a suitable reagent or reagents that could be added separately
to each compound in order to distinguish them. Describe what you would observe with each
compound.
(a) [2]

Reagent or reagents : .

5
Observations :

E : ..

F : ..

(b) [3]

Reagent or reagents : .

Observations :

G : ..

H : ..

Equation for positive test :

..

(c) [3]

Reagent or reagents : .

Observations :

J : ..

K : ..

Equation for positive test :

..

Section C(30 marks)

6
 Answer any 2 questions

18(a) A hydrocarbon, P,, with the formula C6H12 readily decolourises bromine. On reaction with
hot, concentrated, acidifi ed potassium manganate(VII) solution a single organic product, Q, is
obtained. Q gives an orange precipitate when reacted with
w 2,4-dinitrophenylhydrazine,b
dinitrophenylhydrazine,but has
no reaction with Tollens’ reagent.
(i) Explain these observations. [4]
(ii) Draw the skeletal formula
la of P and give its name. [2]
(iii)There
There are several structural isomers of P that also decolourise bromine, but only four of
these structural isomers exhibit geometrical (cis-trans)
(cis isomerism.
Give the structures of any three structural isomers of P that
hat exhibit geometrical (cis-trans)
(cis
isomerism. [3]
(b) A hydrocarbon, W,, with the formula C4H8, reacts with hydrogen bromide, HBr, to give two
products X and Y. X and Y are structural isomers of molecular formula C4H9Br.
Reaction of X with aqueous alkali produces an alcohol, Z, that has no reaction with acidified
dichromate(VI).
(i) Give the structures and names of the compounds W, X, Y, and Z [4]
(ii) When W reacts with hydrogen bromide, more X than Y is produced. Explain why. [2]

19. Noradrenaline is a hormone and neurotransmitter, which is released during stress to

stimulate the heart and increase blood pressure.

(a) State the names of three functional groups in the noradrenaline molecule. [3]

(b) (i) Consider the following two-stage

two stage synthesis of noradrenaline from dihydroxybenzaldehyde.

● Draw the structure of the intermediate Z .

● Suggest reagents for steps 1 and 2 .
● Name the reaction mechanism for step 1

(ii) Dihydroxybenzaldehyde reacts with Br2(aq).

7
● Describe what you would see during this reaction.
● Draw the structure of the product. [6]

(c) Draw the structures of the products when noradrenaline is reacted with
(i) dilute NaOH(aq),
(ii) dilute HCl (aq),
(iii) an excess of ethanoyl chloride, CH3COCl. [4]
(d) Name the new functional groups formed in the reaction in (c)(iii). [2]

20 The amide or peptide link is found in synthetic polyamides and also in naturally-occurring
naturally
proteins.

(a) A polyamide formed by the reaction of propan

propanedioic acid with hexane-1,6
1,6-diamine.
(i) Write a balanced polymerisation equation.
(ii) Draw the repeating unit of the polyamide and label
label the peptide link formed. [4]

(b) Reaction of CH3CH2COCl with CH3NH2 forms an amide. Write structural formula and name
of the amide formed. [2]

(c) The dipeptide shown below is formed from two different amino acids.

(i) Draw the structures of products formed when the dipeptide is heated with dilute acids.
(ii) Draw the structure of the alternative dipeptide that could be formed by these two amino acids.
[3]
(d) The amino acids serine and aspartic acid are shown below.
H2N – CH – COOH H2N – CH – COOH

CH2 CH2

OH COOH

(i) Give the IUPAC name of serine.

(ii) Draw zwitterion of serine and explain its formation.
(ii) Draw the structure of the species formed when aspartic acid reacts with aqueous
sodium hydroxide.
(iii) Draw the structure of the species formed when serine reacts with dilute hydrochloric acid
(iv) Draw the structure of the species formed when aspartic acid reacts with an excess of
bromomethane. [6]

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