2021 Block Test Revision Package (77marks, Target time : 2hrs)

1 (a) The rate of reaction for the reaction 2NO(g) + O2(g) → 2NO2(g) was investigated and
the following kinetics data was obtained.

(i) Explain why nitrogen monoxide is used in large excess. [1]

(ii) Using the graphs above, determine the order of reaction with respect to O2 and
NO, showing your workings clearly. [2]

(iii) State the rate equation for the reaction. Hence, calculate the rate constant,
including its units. [2]

(iv) State how the half–life of oxygen will be affected when the concentration of
nitrogen monoxide is doubled. [1]

(b) Fe2+ ions are also commonly used as a homogenous catalyst in reactions involving two
anions.
(i) The reaction between peroxodisulfate ions, S2O82– and iodide ions is very slow at
room condition.
Explain why this is so. [1]

(ii) Write two equations to show how Fe2+ catalyse the reaction below. [2]

2I– (aq) + S2O82– (aq) → I2 (aq) + 2SO42– (aq)

(iii) With the aid of a Boltzmann distribution curve, explain how Fe2+ ions catalyse the
reaction between S2O82– and iodide ions. [3]

[Total : 12]

1
2 Hydrogen bromide, HBr, is a colourless, or sometimes faint yellow, highly toxic gas with a
sharp, irritating odour. It can also be found as a liquid, either as hydrobromic acid (hydrogen
bromide dissolved in water) or as a compressed gas under pressure (anhydrous hydrogen
bromide). HBr can react with both organic and inorganic compounds.

(a) CH3CBr(CH3)2 can be formed from reacting an alkene with HBr.

(i) Give the structural formula of the alkene. [1]

(ii) Describe the mechanism of this reaction. Show clearly any intermediates that
may be formed and use curly arrows to indicate the movement of electron pairs.
[3]

(iii) Hence explain why CH3CBr(CH3)2 is formed as a major product from this
reaction. [2]

(b) The reaction between HBr and H2O2 can be represented as follows:

H2O2 + 2HBr → 2H2O + Br2

In order to determine the order with respect to HBr, the reaction can be followed by
adding a small, fixed volume of sodium thiosulfate solution to the reaction mixtures at
the start and measuring the time taken for the orange colour of Br2 to appear.

In a series of experiments, the following results were obtained:

volume of volume of volume of time taken for

rate
experiment HBr (aq) / water H2O2(aq) / 0.02 mol dm−3 Br2
/ mol dm−3 s−1
cm3 / cm3 cm3 to be formed / s

1 5.0 20.0 5.0 77

2 10.0 15.0 5.0 38

3 15.0 10.0 5.0 26

4 20.0 5.0 5.0 19

(i) Write an equation between bromine and sodium thiosulfate. Hence explain the
role of sodium thiosulfate in determining the reaction kinetics of this reaction. [2]

(ii) Suggest how the addition of different volumes of water facilitates the comparison
of concentrations of reactants in separate experiments. [1]

(iii) Fill in the blanks in the table above by calculating the rate of each reaction from
the given data. [1]

(iv) Deduce the order of reaction with respect to HBr. [1]

(v) Suggest how the experiment can be modified to determine the order with respect
to H2O2. [1]

(vi) Given that the order with respect to H2O2 is 1, predict whether the above reaction
takes place in a single step or two steps. [1]

[Total: 13]
2
3 The structure of compound A, C13H20O2, is as shown below.

4 2
3 1 O

OH

A
(a) (i) State all the functional groups present in A. [2]

(ii) State the type(s) of stereoisomerism that A can exhibit and describe how such
isomerism can be possible. Draw the stereoisomers. [3]

(iii) State the type of hybridisation of each of the carbons: C1, C2, C3 and C4. Hence
explain which of the C−C bonds is stronger: C1−C2 or C3−C4 bond. [2]

(iv) On heating A with acidified KMnO4(aq), only one organic product B, C11H18O4, is
produced.

Identify B and write an equation for the reaction. [2]

(b) This part question is about two isomeric compounds, C and D, as shown below.

(i) Suggest a simple chemical test to distinguish C from D. [2]

(ii) Suggest a two-step synthetic route to convert C to D. State clearly all reagents
and conditions and any intermediate compound(s) formed. [2]

(c) 1 mol of Compound E, C6H8, reacts with 2 mol of bromine in an inert solvent to form
compound F. Compound E also reacts with hydrogen gas in the presence of Pt to form
compound G. Compound G reacts with chlorine gas in UV light to give only one
monochlorinated product H.

Deduce the identities of E to H. [6]

[Total: 19]

3
4 Methylbenzene is a useful starting precursor for many commercial purposes.

(a) Methylbenzene can be used to synthesize 4−nitromethylbenzene, a common

intermediate for making dyes.

(i) State the reagent(s) and condition(s) for this reaction. [1]

(ii) Describe the mechanism for the nitration of methylbenzene to produce

4−nitromethylbenzene. Show clearly any intermediates that may be formed and
use curly arrows to indicate the movement of electron pairs.
[3]

(b) The following reaction scheme shows the synthetic route for making compound B used
in biochemical studies.

(i) Suggest a structure for the intermediate compound A. [1]

(ii) State the reagent(s) and condition(s) for steps 1 and 2. [2]

(c) The labels on 2 bottles known to contain either methylbenzene or cyclohexene have
accidentally dropped.

Describe a simple chemical test to determine the identity of chemicals, stating the types
of reaction and observations involved. [3]

[Total: 10]

4
5 2-phenylpropan-2-ol is a member of the fragrance structural group Aryl Alkyl Alcohols
(AAA). It can be synthesized from benzene in 3 steps using the following scheme.

2-phenylpropan-2-ol

(a) State the reagents and conditions for Step I and Step II.
[2]

(b) Outline the mechanism for the formation of compound X in step II.
[3]

(c) Another monobrominated product, compound Y, will be formed from step II.
Draw the structure of compound Y.
[1]

(d) Hence, state the expected ratio of the monobrominated compounds X and Y.
[1]

(e) It was observed that the experimental yield of compound X was higher than the
expected yield. Account for the observation.
[2]

[Total : 9]

5
6 Mass spectrometry is an analytical technique which measures the masses of chemical
species present in a sample. A mass spectrum can be used to determine the isotopic
composition of a sample and to elucidate the chemical structure of a chemical compound.

The mass−to−charge ratio, also known as m/e value, is the Mr of chemical species present
in the sample. The peak height ratio gives an indication of the isotopic ratio of an element
in a sample.

In the first experiment, propene was reacted with liquid bromine in inert organic solvent.
The organic products were then extracted and analysed using mass spectrometry. The
mass spectrum is as shown in Figure 2.1.

Relative ratio of peak height

Figure 2.1. Mass spectrum of the products from

reaction of propene with bromine

(i) Draw the structure of the product formed when propene reacts with bromine in inert
organic solvent. [1]

(ii) Based on the m/e values in Fig 2.1, deduce the two isotopes of bromine. [1]

(iii) Using your answers in (i) and (ii), determine the relative abundance of the isotopes
of bromine.

You may assume that carbon, hydrogen and oxygen only exist in one isotopic form
of 12C, 1H and 16O respectively. [1]

(iv) Describe the mechanism for the reaction between propene and bromine in inert
organic solvent.
Show relevant lone pairs and dipoles, and use curly arrows to indicate the movement
of electron pairs. [3]

6
When propene was reacted with aqueous bromine, a different mass spectrum was obtained
as shown in Fig 2.2. There are two additional peaks with greater peak height at m/e ratio of
138 and 140.
Relative ratio of peak height

Fig 2.2 products from reaction of propene with aqueous bromine

(v) Draw a possible structure that accounts for the product with m/e value of 138. [1]

(vi) Explain, with reference to the mechanism you have described in (iv), the m/e and
relative ratio of the two additional peaks. [2]

(vii) Draw the four different possible products that are responsible for the peak at m/e value
of 138. Copy the diagram below to your answer booklet and complete the diagram.

[2]

(viii) Ethanoic acid could be synthesised from propan-1-ol in two steps.

Suggest the structure of compound Y and give the reagents and conditions for each
step.

Step 1 Step 2
CH3CH2CH2OH Compound Y CH3CO2H

[3]

[Total: 14]