Q1.

Which is not a possible product of the reaction of this compound with potassium
hydroxide?

(Total 1 mark)

Q2.
When 2-bromobutane is warmed with potassium hydroxide solution, substitution and
elimination reactions both occur.

Which of these compounds is not produced?

A butan-1-ol

B butan-2-ol

C but-1-ene

D E-but-2-ene

(Total 1 mark)

Q3.
(a) The equation below shows the reaction of 2-bromopropane with an excess of

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 ammonia.

CH3CHBrCH3 + 2NH3 → CH3CH(NH2)CH3 + NH4Br

Name and outline the mechanism involved.

Name of mechanism __________________________________________________

Mechanism

(5)

(b) When 2-bromopropane is heated with ethanolic potassium hydroxide, an elimination

reaction occurs. State the role of potassium hydroxide and outline a mechanism for
this reaction.

Role of potassium hydroxide ____________________________________________

Mechanism

(5)
(Total 10 marks)

Q4.
(a) Complete the mechanism below by drawing appropriate curly arrows.

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 (3)

(b) Draw and name the geometrical E-Z isomers of pent-2-ene.

Isomer 1 Isomer 2

Name _________________________ Name _________________________

(2)

(c) Pent-1-ene reacts with hydrogen bromide to produce 2-bromopentane as the major
product.

(i) Outline the mechanism for this reaction.

(ii) Identify the minor product formed in this reaction.

______________________________________________________________

(iii) Explain why 2-bromopentane is the major product of this reaction.

______________________________________________________________

______________________________________________________________

______________________________________________________________
(7)
(Total 12 marks)

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Q5.
Consider the following reaction in which an alkene is formed from a haloalkane.

(a) Name the haloalkane used in this reaction.

___________________________________________________________________
(1)

(b) Name and outline a mechanism for this reaction.

Name of mechanism __________________________________________________

Mechanism

(4)

(c) Another alkene, which is a structural isomer of but-2-ene, is also formed during this
reaction.

(i) State what is meant by the term structural isomers.

______________________________________________________________

______________________________________________________________

(ii) Draw the structure of this other alkene.

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 (2)
(Total 7 marks)

Q6.
(a) Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with
ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH3)2C=CH2

Name of mechanism __________________________________________________

Mechanism

(4)

(b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with
ethanolic potassium hydroxide.

(i) Explain what is meant by the term stereoisomers.

______________________________________________________________

______________________________________________________________

(ii) Draw the structures and give the names of the two stereoisomers of
but-2-ene.

Stereoisomer 1 Stereoisomer 2

Name _________________________ Name _________________________

(iii) Name this type of stereoisomerism.

______________________________________________________________
(5)

(c) When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide,

2-methylpropan-2-ol is formed as shown by the following equation.

State the role of the hydroxide ions in this reaction.

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 ___________________________________________________________________
(1)

(d) Write an equation for the reaction that occurs when CH3CH2CH2CH2Br reacts with an
excess of ammonia. Name the organic product of this reaction.

Equation ___________________________________________________________

Name of product _____________________________________________________

(3)
(Total 13 marks)

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Mark schemes

Q1.
B

[1]

Q2.
A
butan-1-ol
[1]

Q3.
(a) Name of mechanism: nucleophilic substitution (1)
Mechanism:

Marks SN1 using same points

M2 requires

(b) Role of potassium hydroxide: Base (1)

Mechanism:

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 5
[10]

Q4.
(a) M1 curly arrow from lone pair on oxygen of hydroxide ion to
H atom on C-H adjacent to C-Br
1

M2 curly arrow from single bond of adjacent C-H

to adjacent single bond C-C
(only credit M2 if M1 is being attempted to correct H atom)
1

M3 curly arrow from C-Br bond to side of Br atom

(credit M3 independently)
1

(b) Ml credit a correct structure for either geometrical E-Z isomer and its
designation as either cis or trans.
OR credit two correct geometrical E-Z isomer structures
(ignore the names)
OR credit two correct names for cis pent-2-ene and trans
pent-2-ene (ignore the structures)
1

M2 credit a second mark if all four parts of the required structures and
names are correct.
(credit “linear” structures)
(insist on the alkyl groups being attached clearly by C-C
bonds)
1

(c) (i) Ml curly arrow from middle of C = C bond to H atom on H-Br

(penalise M1 if partial negative charge or formal positive
charge on H)
(penalise Ml if pent-2-ene is used)
1

M2 curly arrow from H-Br bond to side of Br atom

1

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 M3 correct structure for correct secondary carbocation
1

M4 curly arrow from lone pair on bromide ion to the positive

carbon of carbocation, ensuring that bromide ion has a
negative charge.
(with the exception of pent-2-ene, if the wrong alkene is
used, only penalise the structure M3)
(penalise the use of two dots in addition to a covalent bond,
once only)
1

(ii) 1-bromopentane
1

(iii) Ml 2-bromopentane is formed via the secondary (or 2°)

carbocation
1

OR 1-bromopentane is formed via the primary (or 1°)

carbocation
M2 a secondary carbocation is more stable than a primary
carbocation -
award this mark only if the quality of language justifies
the award.
(the argument must involve clear statements about
carbocations)
1
[12]

Q5.
(a) 2-bromobutane;
1

(b) Elimination;
(penalise “nucleophilic” OR “electrophilic” before the word
“elimination”)
1

M1: curly arrow from lone pair on oxygen of hydroxide ion to H atom
on correct C-H adjacent to C-Br;
(penalise M1 if KOH shown as covalent with an arrow
breaking the bond)
1

M2: curly arrow from single bond of adjacent C-H to adjacent

single bond C-C;
(only credit M2 if M1 is being attempted to correct H atom)
1

M3: curly arrow from C-Br bond to side of Br atom;

(credit M3 independently unless arrows contradict)
(Credit possible repeat error from 2(c)(iii) for M3)
(If the wrong haloalkane is used OR but-1-ene is produced,
award MAX. 2 marks for the mechanism)
(If E1 mechanism is used, give full credit in which M1 and

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 M2 are for correct curly arrows on the correct carbocation)

(c) (i) (structural) isomers/hydrocarbons/compounds/they have the same

molecular formula, but different structural formulas/different structures; 1
(penalise statements which are not expressed in good
English and which do not refer clearly to structural isomers
i.e. plural)
(penalise statements which refer to “different (spatial)
arrangements”)
(credit” different displayed formulas”)
(Q of L mark)

(ii) Correct structure for but-1-ene;

1
[7]

Q6.
(a) (base) elimination
(penalise other words before ‘elimination’ e.g. nucleophilic)
1

M1: curly arrow from lone pair of electrons on oxygen of hydroxide ion
(insist on a lone pair of electrons on the oxygen atom and a
negative charge, but only credit this mark if the attack is to a
correct H atom)
1

M2: curly arrow from the middle of the C-H bond to the middle
of the C–C bond
1
(only credit this mark if the arrow originates from the correct
C–H bond and if an attempt has been made at M1)

M3: curly arrow from the middle of the C–Br bond towards/alongside
the Br atom
(credit M3 independently unless the bond breaking is
contradicted by an additional arrow)
(penalise curly arrow if the C–Br has a formal positive
charge)
(credit full marks for an E1 mechanism, with M2 awarded for
a correct curly arrow on the correct carbocation)
(award a maximum of two marks for either an incorrect
haloalkane or an incorrect organic product)
(maximum 2 marks for use of 'sticks' for the haloalkane,
unless RE from 2(b), when credit can be given)

(b) (i) M1: compounds with the same structural formula

1

M2: but the bonds/groups/atoms have different spatial

arrangements or orientation or configuration/are arranged
differently in space/3D
(ignore reference to the same molecular formula for M1)
1

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 (ii) M1: correct structural representation for cis-but-2-ene and
its name or its identification as the cis isomer
1

M2: correct structural representation for trans-but-2-ene

and its name or its identification as the trans isomer
(accept representations which are 90° to linear)
(award one mark for two correct structures but either
wrong/no names)
(maximum 1 mark for an incorrect alkene)
1

(iii) geometric(al) or cis-trans

1

(c) nucleophile or electron pair donor

(penalise ‘base’)
1

(d) CH3CH2CH2CH2Br + 2NH3 → CH3CH2CH2CH2NH2 + NH4Br

(M1 correct product)
(M2 balanced equation using 2NH3 and leading to NH4Br)
(penalise M1 for use of C4H9NH2 or for incorrect haloalkane,
but allow consequent correct balancing of equation with 2
moles of ammonia)
2

(1–)butylamine
(credit 1–aminobutane and butyl–1–amine)
(award QoL mark for correct spelling)
1
[13]

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