M A R K S I D R O P P E D : C H E M I ST R Y

TT REVISION METHOD™ [OCR A LEVEL GAM MA 2022 PAPER 2]

Test Conditions Negatively Mark & Analyse FFS Journal Action Hours Repeat Paper

Grade & FFS Journal AH1 Topic AH2 Topic AH3 Topic Grade & FFS Journal

MID
Q U EST I ON MID TA LLY TOPICS KNOW LE MID TA L LY NOTES
& M AR K S FFS DGE PRACTIC E

1ST

Q 1-15

Multiple Choice
15 Marks

2ND

Q 16

Alkenes
20 Marks

Q 17

Organic Analysis
6 Marks

Q 18

Aromatic Chemistry
7 Marks

Q 19

Aromatic Compounds
18 Marks

Q 20

Organic Multi-topic
21 Marks

Q 21

Organic Synthesis
11 Marks
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SECTION A

You should spend a maximum of 20 minutes on this section.

Write your answer to each question in the box provided.

Answer all the questions.

1 Which alkane has the highest boiling point?

A CH3(CH2)5CH3

B (CH3)3CCH(CH3)2

C CH3(CH2)3CH(CH3)2

D (CH3)2CHCH2CH(CH3)2

Your answer
[1]

2 Butane reacts with chlorine in the presence of ultraviolet radiation to form a mixture of organic
products.

Which equation shows a propagation step in the mechanism for this reaction?

A Cl 2 → •Cl + •Cl

B •Cl + •C4H8Cl → C4H8Cl 2

C C4H9Cl + •Cl → C4H8Cl 2 + •H

D •Cl + C4H9Cl → •C4H8Cl + HCl

Your answer
[1]

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3 What is the name of the compound below?

H CH3
C

C
H 3C CH2 CH2 CH2 CH3

A 3-Propylpent-2-ene

B 3-Propylpent-3-ene

C 3-Ethylhex-2-ene

D 4-Ethylhex-4-ene

Your answer
[1]

4 The structure of a stereoisomer is shown below.

H3C CH(CH3)2

C C

CH3CH2 CH2CH2CH3

Which term correctly describes this stereoisomer?

A cis-

B trans-

C E-

D Z-

Your answer
[1]

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5 Which types of bonds are broken and formed in the reaction of ethene and bromine?

Types of bond broken Types of bond formed

A σ π
B π σ
C σ and π π
D σ and π σ

Your answer
[1]

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6 What is the organic product of the reaction below?

CH2Cl

KOH(aq)

Cl

CH2OH

Cl

CH2Cl

OH

CH2OH

OH

HO CH2Cl

Cl

Your answer
[1]

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7 What is the number of chiral carbon atoms in the steroid molecule below?

OH

A 5

B 6

C 7

D 8

Your answer
[1]

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8 Phenol reacts with bromine.

Which is the least likely organic product?

OH

Br

Br

OH

Br Br
B

OH

Br
C

Br

OH

Br Br

Br

Your answer
[1]

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9 The repeat unit of a polymer is shown below.

H H H H O

O C C O C C C C

H H O H H

Which monomers could form this polymer?

OH HO
A
HO OH

OH
HO OH
B
HO

O O
HO OH
C

HO OH

O O

D HO
HO OH OH

Your answer
[1]

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10 Which compound shows 4 peaks in its carbon-13 NMR spectrum?

Your answer
[1]

11 A student reacts 4.50 g of C6H5NH2 with excess CH3COCl in the reaction below.

C6H5NH2 + CH3COCl → C6H5NHCOCH3 + HCl

Mr = 93.0 Mr = 135.0

The reaction produces 3.25 g of C6H5NHCOCH3.

What is the percentage yield of C6H5NHCOCH3?

A 49.8

B 68.9

C 72.2

D 95.4

Your answer
[1]

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12 A compound produces the 13C NMR spectrum below.

80 70 60 50 40 30 20 10 0
chemical shift, d / ppm

Which compound could have produced this spectrum?

A Propane

B 2-Methylbutane

C 2-Methylpropan-1-ol

D 2-Methylpropan-2-ol

Your answer
[1]

13 A carbonyl compound is reacted with NaBH4.

Which compound(s) could be formed?

1 2-Methylpentan-2-ol

2 2-Methylpentan-1-ol

3 3-Methylpentan-2-ol

A 1, 2 and 3

B Only 1 and 2

C Only 2 and 3

D Only 1

Your answer
[1]

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14 Which chemical(s) can react with phenol?

1 Potassium hydroxide

2 Ethanoyl chloride

3 Nitric acid

A 1, 2 and 3

B Only 1 and 2

C Only 2 and 3

D Only 1

Your answer
[1]

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15 The structure of a compound used to treat influenza is shown below.

O
O

HN

NH2
O

Which functional group(s) is/are in a molecule of the compound?

1 Ester

2 Secondary amide

3 Ketone

A 1, 2 and 3

B Only 1 and 2

C Only 2 and 3

D Only 1

Your answer
[1]

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SECTION B

Answer all the questions.

16 This question is about unsaturated hydrocarbons.

(a) Compound A and compound B are isomers.

compound A compound B

Compound A has a lower melting point than compound B.

Suggest why.

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(b) Compound C, CH3CH2CH=CHCH2CH2OH, exists as cis and trans stereoisomers.

(i) Name compound C.

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(ii) Define the term stereoisomers.

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(iii) Draw the structures of the cis and trans stereoisomers of compound C.

cis trans

[2]

(c) The C=C group in an alkene contains a π-bond.

Complete the diagram below to show how p-orbitals are involved in the formation of a π-bond.

[1]

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(d) Compound D, shown below, reacts with hydrogen bromide by electrophilic addition. A mixture
of two organic compounds, E and F, is formed.

CH3 CH2CH3
HBr
C C Mixture of organic compounds E and F

CH3 H

compound D

(i) Suggest how an HBr molecule can act as an electrophile.

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(ii) Draw the structures of the two organic compounds E and F.

E F
[2]

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(iii) Outline the mechanism of the reaction between compound D and hydrogen bromide to
form either compound E or compound F.

Include curly arrows and relevant dipoles.

[3]

(iv) Which of E or F is the major organic product?

Explain your answer.

Major organic product .......................................................................................................

Explanation .......................................................................................................................

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(e) Myrcene, C10H16, is a naturally occurring hydrocarbon containing more than one
carbon-carbon double bond.

myrcene

(i) Reaction of 204 mg of myrcene with hydrogen gas produces a saturated alkane.

Calculate the volume of hydrogen gas, in cm3 and measured at RTP, needed for this reaction.

Show your working.

volume = .................................................. cm3 [2]

(ii) β-Carotene is a naturally occurring unsaturated hydrocarbon found in carrots.

A β-carotene molecule contains 40 carbon atoms, has two rings, and a branched chain.

0.0200 mol of β-carotene reacts with 5.28 dm3 of hydrogen gas to form a saturated
hydrocarbon.

Using molecular formulae, construct a balanced equation for this reaction.

Include relevant calculations and reasoning.

Equation ...................................................................................................................... [4]

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17* Compound L is an organic compound containing carbon, hydrogen and oxygen only.
The 1H NMR spectrum of compound L is shown below.
The numbers by the peaks are the relative peak areas.

3
2
2

5 4 3 2 1 0
chemical shift, / ppm

Compound L is refluxed with aqueous hydrochloric acid, forming two organic compounds M
and N. The infrared spectra of M and N are shown below.

Infrared spectrum of M
Item removed due to third party copyright restrictions.

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Infrared spectrum of N

100

transmittance
(%) 50

0
4000 3000 2000 1500 1000 500
wavenumber / cm–1

Use the information provided to suggest a structure for compound L.

Show all of your reasoning.

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18 A student investigates reactions of aromatic compounds.

(a) The student first carries out the reaction shown below.

+ FeCl3
+ HCl

quinol Compound E

(i) The student obtains a very low yield of compound E.

The student obtains a much higher yield of a different organic product with molecular
formula C14H22O2.

Suggest an identity for the organic product C14H22O2 and draw its structure below.

[1]

(ii) The student is told by a friend that the FeCl3 catalyst is not needed because quinol is more
reactive than benzene.

Explain why the student’s friend is correct.

You may draw a diagram to support your answer.

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(b) 4-Nitrobenzoic acid is an important compound in chemical synthesis. The flowchart below shows a
synthesis involving 4-nitrobenzoic acid.

product
step 1 step 2

Compound F

(i) State suitable reactant(s) and conditions for step 1.

[1]

(ii) In step 2, the –NO2 group in compound F is reduced by tin and concentrated
hydrochloric acid.

Write an equation for the reduction of compound F.

Show the structures of any organic compounds involved.

[2]

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19 Dettol® is a disinfectant containing the antiseptic chloroxylenol, shown below.

OH

H 3C CH3

Cl
chloroxylenol

(a) Chloroxylenol is a weak Brønsted–Lowry acid.

(i) What is the systematic name of chloroxylenol?

...................................................................................................................................... [1]

(ii) Predict the number of peaks in a 13C NMR spectrum of chloroxylenol.

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(iii) Name the functional group responsible for the acidity of chloroxylenol and describe a
simple test which would confirm the presence of this group.

Functional group ................................................................................................................

Test ....................................................................................................................................

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...................................................................................................................................... [2]

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(iv) A student measures the pH of the contents in a bottle of Dettol® as 5.14.

The label on the bottle shows the percentage of chloroxylenol in Dettol® as 4.80%
i.e. 100 cm3 of Dettol® contains 4.80 g of chloroxylenol.

Assume the following:

• Chloroxylenol is the only acidic component in Dettol®.
• Chloroxylenol is a weak monobasic acid.
• The density of Dettol® is 1.00 g cm−3.

Write the equation, using molecular formulae, for the acid dissociation of chloroxylenol.

Calculate the acid dissociation constant, Ka, for chloroxylenol.

Ka = .......................................... mol dm−3 [5]

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(b) Dettol® contains other chemicals including α-terpineol, shown below.

(i) α-Terpineol is a chiral compound.

Show with an asterisk, (*), the chiral centre(s) in the structure of α-terpineol.

OH

α-terpineol
[1]

(ii) α-Terpineol meets the requirements for E / Z isomerism.

However, only one E / Z isomer of α-terpineol exists.

Explain
• why α-terpineol meets the requirements for E / Z isomerism
• whether α-terpineol is an E- or Z- isomer
• why only one E / Z isomer of α-terpineol exists.

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(iii) α-Terpineol contains two functional groups.

For each functional group, choose a reagent that reacts with that group only.
Draw the structures for the organic products of the reactions.

Show structures for organic compounds.

Reagent(s) ................................................................................................................................

Name of functional group that reacts ........................................................................................

Structure of organic product

Reagent(s) ................................................................................................................................

Name of functional group that reacts ........................................................................................

Structure of organic product

[4]

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20 Molecules with more than one functional group are useful chemical ‘building blocks’.

(a) Compound D, CH3CH(OH)CH2NH2, is an intermediate in the synthesis of a variety of drugs.

(i) Compound D can be synthesised from ethanal, CH3CHO.

Devise a two-step synthesis of compound D from ethanal.

Give details of appropriate reagents and relevant conditions.
Write an equation for each step, showing clearly all organic compounds.

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(ii) Explain why compound D is very soluble in water.

Use a diagram in your answer.

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(iii) Compound D reacts with propanedioic acid, HOOCCH2COOH, to form a

condensation polymer.

Draw a possible repeat unit of this condensation polymer.

Show clearly any functional group present in the repeat unit.

[2]

(b) Serine, shown below, is an amino acid.

(i)

Use electron repulsion theory to predict the shape of the bonds around atoms A and B.

Give relevant bond angles around atoms A and B.

Give reasons for your answers.

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(ii) A student adds an excess of aqueous sodium hydroxide to a sample of solid serine.
The student then purifies the resulting reaction mixture to obtain a pure sample of an ionic
organic product.

Draw the structure of the ionic organic compound obtained.

Outline the steps that the student could carry out to obtain a pure sample of the organic
product from the reaction mixture.

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…………………………………………………………………………………………. [3]

(c) Tabtoxin is a poisonous substance produced by bacteria found in lilac trees.

tabtoxin

(i) Identify the chiral centres present in a molecule of tabtoxin.

On the structure above, mark each chiral centre with an asterisk, *. [1]

(ii) Tabtoxin can be broken down by alkaline hydrolysis.

Draw the structures of all the organic products of the alkaline hydrolysis of tabtoxin.

[4]
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21 This question is about two compounds used in medicine.

(a) Cis-platin, PtCl2(NH3)2, is a complex of platinum which is used in cancer treatment.

(i) What is the oxidation number of platinum in cis-platin?

............................ [1]

(ii) Cis-platin is prepared in a ligand substitution reaction which takes place in multiple steps.

The equation for the final step forming cis-platin is shown below.

[PtCl 3(NH3)]– + NH3 → PtCl 2(NH3)2 + Cl –

cis-platin

In the box, outline the mechanism for the formation of cis-platin from [PtCl 3(NH3)]–.
Use curly arrows and lone pairs where appropriate.

Cl Cl _
Pt + Cl
H 3N NH3
cis-platin

[2]

(b) Paracetamol is a solid organic compound used in tablets as a painkiller.

HO N

C CH3
paracetamol
O

(i) Name the functional groups present in paracetamol.

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...................................................................... [2]

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(ii)* A chemist prepares a pure solid sample of paracetamol from 4-nitrophenol in two stages:

H
Stage 1 Stage 2
HO NO2 Intermediate HO N
CH3COCl
C CH3
4-nitrophenol paracetamol
O

Describe a two-stage synthesis of 5.00 g of pure paracetamol from 4-nitrophenol. The

overall percentage yield of paracetamol from 4-nitrophenol is 40.0%.

In your answer, include the mass of 4-nitrophenol required, the reagents and intermediate,
and details of the purification of paracetamol. [6]

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Additional answer space if required.

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