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SECTION A [15 marks]

Answer all questions in this section. Indicate the correct answer on the space provided in page 5

1. The structural formula of an organic compound is shown below. Which is correct about the
number of sp2 and sp3 hybridised C atoms in the molecule?
sp2 sp3
A 5 5
B 4 5
C 5 4
D 6 4

2. What is the correct name of the molecule with the skeletal formula shown?

A. 5-hydroxy-2,3-dimethylhex-2-ene B. 2-hydroxy4,5-dimethylhex-4-ene
C. 2,3-dimethyl-2-hexen-5-ol D. 4,5-dimethyl-4-hexen-2-ol

3. The diagram shows the structure of 1,3-butadiene.

The addition reaction between 1,3-butadiene and two molecules of hydrogen bromide, HBr,
can produce three structurally isomeric products. How many of these products have at least
one chiral centre?
A. 0 B. 1 C. 2 D. 3

4. When heated with chlorine under ultraviolet, the hydrocarbon 2,2-dimethylbutane undergoes
free radical substitution. In a propagation step a free radical X• is formed.

How many different structures of X• are possible?

A. 2 B. 3 C. 4 D. 5

5. Which of the following reaction schemes can be used for the preparation of benzoic acid?

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6. The reaction between boiling methylbenzene and chlorine takes place in a number of steps to
give several products. Which of the following could be one of the steps?

7. A reaction pathway diagram is shown.

The four reactions that follow are all exothermic. Which reaction would not have such a
pathway?

8. Haloalkanes show trends in their physical and chemical properties. Which properties steadily
increase from C2H5Cl to C2H5Br to C2H5I ?
I. the polarity of the carbon-halogen bond
II. the boiling point of the haloalkane
III. the rate of reaction of the haloalkane with nucleophiles
IV. the preference to undergoes SN2 mechanism
A. I and IV B. II and III
C. I and II D. III and IV

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9. Y gives product Z after mild oxidation. Z gives a positive result with Tollens’ reagent and with
2,4-dinitrophenylhydrazine reagent. What could be the identity of Y?
A. pentan-1-ol B. pentan-2-ol C. pentan-2,3-diol D. pentanal

10. A sample of butan-2-one is treated with lithium tetrahydridoaluminate(III) and then with
concentrated sulphuric acid at 180°C. Which of the following could not apply to the product
formed?
A. It shows optical isomerism.
B. It undergoes nucleophilic addition reaction.
C. It reacts with sodium metal to give hydrogen.
D. It decolourises acidified solution of potassium manganate(VII)

11. Which reagent cannot be used to distinguish between ethanal and propanone?
A. acidified sodium dichromate(VI) solution
B. alkaline aqueous iodine
C. cold acidified potassium manganate(VII) solution
D. Fehling’s reagent

12. The structural formulae of two compounds A and B are shown below.

Which statements about these compounds are correct?

I. The two compounds are structural isomers of each other.
II. The empirical formula of both compounds is C3H6O.
III. Both compounds are carboxylic acids.
IV. Both compounds can undergoes hydrolysis.
A. I and IV B. II and III
C. I and II D. I, III and IV

13. The ester CH3CH2CH2COOCH2CH(CH3)2 was hydrolysed under acidic conditions. What are
the organic products of this hydrolysis?
A. butanoic acid and 2-methylpropan-1-ol
B. butanoic acid and 2-methylpropan-2-ol
C. butan-1-ol and 2-methylpropanoic acid
D. propanoic acid and 2-methylpropan-1-ol

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14. The following reaction between phenol and a compound X produces an orange dye

Which reagents can be used to produce X?

15. GABA is a neuro-transmitter released by red algae which encourages shellfish larvae to settle
on the ocean bed.
H2NCH2CH2CH2COOH GABA
In what way does GABA differ from amino acids obtained by the hydrolysis of protein?
A It does not form a zwitterion. B It is not soluble in water.
C It is not a 2-aminocarboxylic acid. D It does not form a polyamide linkage

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SMK TASEK UTARA, JOHOR BAHRU
UJIAN PENILAIAN PRA-PENTAKSIRAN (2) SEM 3 2017
SUBJECT : CHEMISTRY
Name : ____________________________________ Tingkatan : UPPER 6 ____________
Section A [15 marks]

1 6 11

2 7 12

3 8 13

4 9 14

5 10 15

Section B [15 marks]

Answer all questions in this section

16. A reaction sequence based on propan-1-ol is shown.

(a) Suggest a reagent and condition for reaction 1 and reaction 2 to occur : [2 marks]
Reaction 1 : ……………………………………………………………………………
Reaction 2 : ……………………………………………………………………………

(b) Complete the reaction sequence by filling the molecular structure of A and B in the boxes
provided. [2 marks]

(c) Suggest a chemical test that can be used to distinguish ethanoic acid from compound B
proposed in (b) [3 marks]
………………………………………………………………………………………………....
………………………………………………………………………………………………....
………………………………………………………………………………………………....
………………………………………………………………………………………………....

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17. Glutamic acid is one of the natural amino acid found naturally in kombu broth, a type of
seaweed, which eventually, can be used to produce monosodium glutamate (MSG). The
molecular structure of glutamic acid is given below

(a) Give the IUPAC name of glutamic acid. [1 mark]

………………………………………………………………………………………………....
(b) When two glutamic acid reacted, it can form dipeptide that is bonded by peptide linkage.
(i) Define the term peptide linkage [1 mark]
………………………………………………………………………………………………..
………………………………………………………………………………………………..
(ii) Draw the structures of dipeptide that can be formed by reacting two glutamic acid
[2 marks]

(c) Glutamic acid shows variation in chemical properties due to the presence of carboxyl group
and amino group. Draw the molecular structure of the product formed when glutamic acid
react with the following compound [2 marks]
(i) dilute hydrochloric acid (ii) methanol with concentrated sulphuric acid
under reflux.

(d) Write the chemical equation for the reaction between glutamic acid with sodium hydroxide
to produce monosodium glutamate (MSG) and state one of its application in our daily life
Equation : [2 marks]

Application : …………………………………………………………………………………………

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Section C [30 marks]
Answer any two of the three questions below

18. Compound E, with molecular mass, MR = 106.5, is an optically active primary haloalkane has
the following composition by mass - 56.34% of carbon ; 10.33% of hydrogen and 33.33 % of
chlorine.

(a) Calculate the empirical formula and molecular formula of E [4 marks]

(b) When compound E react with aqueous sodium hydroxide under reflux to form compound F.
F decolourised hot acidified potassium dichromate(VI) to produce a compound G which
reacts with potassium hydroxide to form salt and water. Compound E can also react with
magnesium in dry ether to form compound H and H further react with propanone followed
by acidic hydrolysis to form compound J.
(i) Deduce the molecular structure of E, F, G, H and J [5 marks]
(ii) Write all the equations for the reactions that occurred. [6 marks]

19. Paracetamol is commonly used as modern medicine to treat mild fever and headache. The
structure of paracetamol is given below

(a) Using suitable reagents and conditions, propose a reaction scheme to synthesis paracetamol
starting from phenol. [5 marks]

(b) Draw the molecular structure of the products for the reaction of paracetamol with
(i) hydrochloric acid under reflux [2 marks]
(ii) sodium hydroxide under reflux [2 marks]

(c) When paracetamol is treated with aniline under suitable condition, it may be use to produce
a yellow colour type of paracetamol which enhance the appearances suitable for children to
consume. The reaction scheme for reaction of paracetamol and aniline is describe below

Based on the reaction scheme above

(i) State the reagents and conditions for x and y [3 marks]
(ii) Draw the molecular structure of M and N [2 marks]
(iii) State the type of reaction occur from M to form N [1 mark]

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20. An optically active ester, P, with the molecular formula C5H10O2 undergoes acidic hydrolysis
to form compound Q and an optical active compound R. Both Q and R react with acidified
potassium manganate (VII), however only organic compound S is formed from either Q and R,
where S can react with both 2,4-dinitrophenylhydrazine and iodoform test.

(a) Explain the above observations using suitable equations and write the structural formulae of
P, Q, R and S [10 marks]

(b) Compound T is an optically active carboxylic acid that is an isomer of ester P.

(i) Name compound T. [1 mark]
(ii) Compare and explain the boiling point of compound P and T. [4 marks]

=================== END OF QUESTION PAPER ===================

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