Temasek Junior College 2022 Jc2 March Common Test Higher 2: Worked Solutions
Temasek Junior College 2022 Jc2 March Common Test Higher 2: Worked Solutions
CANDIDATE
WORKED SOLUTIONS
NAME
SUBJECT
CG / 21 TUTOR’S NAME
CHEMISTRY 9729
Section C Free Response 24 March 2022
1 hour
Candidates answer on the Question Paper.
Write your name, CG and subject tutor’s name on all the work you hand in.
If additional space is required, you should use the pages at the end of this booklet. The question number must be
shown clearly.
Section C Q1 / 20
Q2 / 20
TOTAL / 40
(i) Write a balanced equation for the reaction between 2-bromobutane and aqueous sodium
hydroxide. [1]
•
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(iii) Calculate the initial rate for each of the three experiments and use the results to deduce
the order of reaction with respect to 2-bromobutane and sodium hydroxide. Explain your
reasoning. [3]
Volume of NaOH
initial rate ∝ time
(iv) Hence, state the rate equation and name the mechanism of the reaction between 2-
bromobutane and sodium hydroxide. [1]
✓ rate = k[2-bromobutane]
✓ SN1
1 mark for 2 marking points
Allow ECF from (iii). If order of reaction wrt [OH-] was deduced to be 1,
rate = k[2-bromobutane][OH-] SN2
Do not accept other incorrect orders of reaction with respect to hydroxide e.g. -1
(v) The experiment was separately repeated using 2-bromobut-1-ene and 2-chlorobutane
instead of 2-bromobutane.
Cl
2-bromobut-1-ene 2-chlorobutane
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(b) Two common qualitative analysis tests are used to differentiate between the different classes of
alkyl halides.
These two tests were performed on a series of alkyl halides and the results are tabulated in
Table 1.2.
Table 1.2
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Alkyl Halide Time taken for precipitate Time taken for precipitate
to appear in alcoholic to appear in sodium iodide
silver nitrate test / propanone test
Due to the conditions used, alkyl halides react predominantly by SN1 mechanism in test 1.
However they react predominantly by SN2 mechanism in test 2.
(i) By considering the structure of the alkyl halides used in the tests and the information in
Table 1.2, explain why the results confirm the predominant mechanism undergone in each
test. [3]
✓ Tertiary halogenoalkane (2-bromo-2-methylpropane) reacted fastest in the test 1
(AgNO3 test) while it hardly showed any reaction in test 2 (NaI test).
✓ Primary halogenoalkane (1-bromobutane) reacted slowest in test 1 while it reacted the
fastest in test 2. [1 mark for observation]
• Tertiary halogenoalkanes form stable carbocations and tend to react via SN1
mechanism, which can be seen from its fast reaction in the test 1. [1]
(ii) The equation for the reaction between ethanol and 2-bromobutane is shown in Fig 1.1.
H H
Br OCH2CH3
Fig 1.1
Using Fig 1.1 and the information provided in (b)(i), describe the mechanism of the
reaction between ethanol and 2-bromobutane in test 1. Show relevant lone pairs and
dipoles, and use curly arrows to indicate the movement of electron pairs. [2]
√ SN1 mechanism
CH 2CH 3 CH2CH3
+ − slow -
CH3 C Br CH3 C+ + Br
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H H √
1 mark: step 1 with arrows, dipoles, movement of electrons, slow/fast steps
1 mark: name of mechanism and step 2
(not necessary to show how H+ is extracted from the resulting compound)
(iii) A sample of optically pure 2-bromobutane rotated plane-polarised light by +89. Describe
and explain the optical activity of the organic product formed when 2-bromobutane is
reacted with ethanolic silver nitrate in test 1. [2]
✓ The product does not rotate plane polarised light.
✓ A racemic mixture is formed.
✓ Carbocation is planar around the electron-deficient carbon atom.
✓ Nucleophile attacks the carbocation from either side of the plane with equal probability,
forming equimolar amounts of enantiomers.
2 ticks = 1 mark
(c) X is a compound made from two Period 3 elements. X reacts with excess water to form a
solution, FA 1.
When aqueous silver nitrate was added to a portion of FA 1, a white precipitate Y was observed.
When sodium carbonate was added to another portion of FA 1, effervescence of gas Z was
observed. FA 1 forms a white precipitate with aqueous sodium hydroxide, which is soluble in
excess aqueous sodium hydroxide.
(i) State the identities of
• compound X,
• the white precipitate Y, and
• the gas Z formed. [2]
✓ X is AlCl3
✓ White ppt Y is AgCl
✓ Gas Z is CO2
3 marking points – 2 marks, 2 marking points – 1 mark
(ii) With the aid of equations, explain the reactions that take place when X is mixed with
excess water. [2]
• AlCl3 undergoes hydration and hydrolysis. The high charge density of aluminium
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2 (a) (i) Aldehydes such as propanal undergo nucleophilic addition reaction to form 2-
hydroxybutyronitrile, shown below.
State the reagent and condition for the above reaction. [1]
Under acidic conditions, aldehydes undergo nucleophilic addition reaction with alcohols. In this
reaction, an aldehyde molecule reacts with 2 equivalent of alcohol molecules reversibly to form
acetals. The reaction goes through the formation of a hemiacetal, as shown below.
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1 for each correct step with use of curly arrows, charges and lone pairs
Accept step 3 without H2O to remove H+, but must still show curly arrow.
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Reaction of propanal with ethanol would be slower than with HCN, as the ethanol
is a weaker nucleophile than CN- since the former is neutral and attacks the
electron deficient carbon less readily.
(b) Compound E reacts with hot aqueous KOH. Analysis shows that among the mixture of
products, a non-ionic product F, C10H12O, is formed.
The phenol OH undergoes acid-base reaction with KOH to form a phenoxide ion
and undergoes intramolecular nucleophilic substitution with the chloroalkane to
form a cyclic ether.
(iii) Other than iron(III) chloride, suggest another chemical test to distinguish E from F.
Construct an equation for the reaction involved. [3]
Alternative test 1
Heat both compounds with NaOH(aq), acidify with HNO3(aq) and add AgNO3(aq).
for both observation
E: white ppt of AgCl
F: no white ppt of AgCl
for both correct equations
Alternative test 2
Alternative test 3
(c) Hydrocarbon G, C9H8, reacts with equimolar of steam in the presence of phosphoric acid to
give C9H10O, which has 2 pairs of enantiomers. Treatment of C9H10O with hot acidified
potassium dichromate produces I, C9H8O.
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Deduce the structures of G, H, I and J, explaining the chemistry of the reactions involved. [9]
Observation Deduction
G H I J
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[Total: 20]