Shanghai Singapore International School

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 . Which compound is a member of the same homologous series as 1-bromobutane?

A. 1-bromopropane

B. 1-chlorobutane

C. 1-bromobut-1-ene

D. 1,1-dibromobutane

. Which statement is true about a free radical?

A. It must contain at least one unpaired electron.

B. It must contain at least one non-bonding pair of electrons.

C. It can be formed by the heterolytic fission of a covalent bond.

D. It can only react with another free radical.

. Which species will react most readily with methane?

A. Br+

B. Br

C. Br2

.
D. Br
. Which functional groups are present in a molecule of testosterone?

I. hydroxyl
II. alkenyl
III. carbonyl
A. I and II only
B. I and III only
C. II and III only
D. I, II and III

. Which is the best way to obtain ethanoic acid from ethanol?

A. Refluxing ethanol with acidified potassium dichromate(VI).

B. Reacting ethanol with acidified potassium dichromate and distilling off the product as it
is formed.

C. Heating ethanol in the presence of concentrated sulphuric acid.

D. Heating ethanol in the presence of sodium hydroxide solution.

 . An organic compound X reacts with warm potassium dichromate(VI) solution to form a
product that can react with calcium carbonate to give off carbon dioxide.

Which could be a possible formula for X?

A. CH3CH(OH)CH3

B. CH3COOH

C. CH3COCH3

D. CH3CHO

. Which two step synthesis could be used to convert ethene into

1,1,2,2-tetrachloroethane?
A. Addition of hydrogen followed by reaction with chlorine in ultraviolet light.
B. Addition of chlorine followed by reaction with water.
C. Addition of hydrogen chloride followed by substitution with sodium chloride.
D. Addition of chlorine followed by dehydration with concentrated sulfuric acid.

. What is the best way to minimise the random uncertainty when performing an acid-
base titration?

A. Use a different pipette

B. Use a pH meter rather than an indicator to determine the end point

C. Repeat the titration several times

D. Keeping your eye at the same height as the meniscus when reading the burette

. Which will give the greatest uncertainty when measuring 50.00 cm 3 of a liquid?

A. Graduated 50cm3 pipette

B. Graduated 50 cm3 burette

C. 50 cm3 volumetric flask

D. 50cm3 measuring cylinder

 . A student performed an experiment three times to determine a value for the melting
point of a compound. The three values she obtained were 112 oC, 111 oC and 112 oC.
The literature value for the melting point is 122 oC. Which best describes her data?

A. Her measurements involve low accuracy and high precision.

B. Her measurements involve low accuracy and low precision.

C. Her measurements involve high accuracy and high precision.

D. Her measurements involve high accuracy and low precision

1. An organic compound containing only carbon and hydrogen has an index of hydrogen
deficiency (IHD) of one. Which statement about the compound is consistent with this
information.

A. It is an alkyne.

B. It is a cycloalkane.

C. It contains an aldehyde functional group.

D. It is a branched alkane.

1. Which compounds contains at least one peak in its 1H NMR spectrum that is split into a
doublet?

A. CH3CH2COOH

B. CH2CH2

C. (CH3)CHCOCH2CH3

D. (CH3)3CCOOH
1. Which isomer of C3H6O2 has a different number of peaks to the other three isomers in
its 1H NMR spectrum?

A. CH3CH2COOH

B. CH3COOCH3

C. HCOOCH2CH3

D. CH3OCH2CHO

1. Propanal, CH3CH2CHO, undergoes complete fragmentation in a mass spectrometer.

Which value for m/z will not show up as a line in its mass spectrum?

A. 15

B. 29

C. 44

D. 58

1. Which is a correct statement about the use of spectroscopy to determine the structure
of an organic compound?

A. X-ray crystallography provides information on the bond angles in a molecule of the

compound.

B. Infrared spectroscopy can be used to help determine the number of hydrogen atoms in
a molecule of the compound.

C. Mass spectrometry can be used to determine the bond lengths in a molecule of the
compound.

D. 1H NMR provides information on the chemical environment of each carbon atom in a

molecule of the compound.
. The infrared spectrum of a compound shows a very broad absorption centred at
3325 cm-1 but no absorption at around 1700 cm-1. Which class of compound is it most
likely to belong to?

A. carboxylic acid

B. aldehyde

C. ester

D. alcohol
7. The biopharmaceutical industry is now a global contributor to the world economy.

(a) Atorvastatin, a drug used to lower cholesterol, recently gained attention from the global
media.

Atorvastatin has the structure shown below.

II. III.

N OH
O

HO OH O

I. IV.

Identify the four functional groups, I, II, III and IV. [2]

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(Question 7 continued)

(b) Bute, a painkiller used on horses, has caused widespread concern recently because
analytical tests showed that it entered the food chain through horse meat labelled as beef.
The drug is suspected of causing cancer.

(i) Analysis of a sample of bute carried out in a food safety laboratory gave the
following elemental percentage compositions by mass:

Element Percentage
C 73.99
H 6.55
N 9.09
O Remainder

Calculate the empirical formula of bute, showing your working. [3]

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(ii) The molar mass, M, of bute, is 308.37gmol1. Calculate the molecular formula. [1]

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(Question 7 continued)

(iii) Deduce the degree of unsaturation (index of hydrogen deficiency IHD) of bute. [1]

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(iv) The infrared (IR) spectrum of bute is shown below.

100
Transmittance / %

50

B
0
4000 3000 2000 1500 1000 500
1
Wavenumber / cm

[Source: SDBS web: www.sdbs.riodb.aist.go.jp (National Institute of Advanced Industrial Science and Technology, 2014)]

Using information from section 26 of the data booklet, identify the bonds
corresponding to A and B. [1]

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(Question 7 continued)

(v) Based on analysis of the IR spectrum, predict, with an explanation, one bond
containing oxygen and one bond containing nitrogen that could not be present in
the structure. [2]

Bond containing oxygen not present in structure:

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Bond containing nitrogen not present in structure:

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Explanation:

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(Question 7 continued)

(c) An alcohol, X, of molecular formula C3H8O, used as a disinfectant in hospitals, has the
following 1HNMR spectrum:

10 9 8 7 6 5 4 3 2 1 0
Chemical shift / ppm

[Source: SDBS web: www.sdbs.riodb.aist.go.jp (National Institute of Advanced Industrial Science and Technology, 2014)]

The three peaks in the 1HNMR spectrum of X have chemical shift values centred at
= 4.0, 2.3 and 1.2ppm.

(i) From the integration trace, estimate the ratio of hydrogen atoms in different
chemical environments. [1]

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(ii) Deduce the full structural formula of X. [1]

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(Question 7 continued)

(iii) Y is an isomer of X containing a different functional group. State the condensed

structural formula of Y. [1]

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(iv) Compare and contrast the expected mass spectra of X and Y using section 28 of the
data booklet. [2]

One similarity:

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One difference:

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(Question 7 continued)

(v) Both X and Y are soluble in water. Deduce whether or not both X and Y show
hydrogen bonding with water molecules, representing any hydrogen bonding
present by means of a diagram. [2]

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(Question 7 continued)

(d) The two isomers of [Pt(NH3)2Cl2] are crystalline. One of the isomers is widely used as a
drug in the treatment of cancer.

(i) Draw both isomers of the complex. [1]

(ii) Explain the polarity of each isomer, using a diagram for each isomer to support
your answer. [2]

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(iii) State a suitable method (other than looking at dipole moments) to distinguish
between the two isomers. [1]

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(Question 7 continued)

(iv) Compare and contrast the bonding types formed by nitrogen in [Pt(NH3)2Cl2]. [2]

Similarity:

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Difference:

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(v) Deduce all of the intermolecular forces between molecules of ammonia. [2]

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