13 Halogenoalkanes

AQA Chemistry Exam-style mark scheme

Question
Answer Marks Guidance
number
1a Electron pair donor 1
OR
Species which uses a pair of electrons to form a co-
ordinate / covalent bond.
1b Replacement of the halogen (atom) (by the 1 They must describe the idea of
nucleophile) substitution in a halogenoalkane.
OR Penalise reference to ‘halogen
molecule’ and penalise the idea
The carbon–halogen bond / C–X breaks and a bond
forms with the nucleophile or between the carbon that the halogenoalkane contains
and the nucleophile. a halide.

1c Splitting molecules using / by water 1 NOT simply the reaction with

water or simply the addition of
OR
water.
breaking / splitting / dissociating (C–X) bond(s) /
Ignore ‘compound’.
using / by water.
1d Heat energy / enthalpy required / needed / absorbed 1 Ignore bond formation.
to break / split it / the carbon–halogen bond
OR
Heat energy / enthalpy required / needed / absorbed
Ignore ‘average’.
(at constant pressure) for homolysis of the (C–X /
the carbon–halogen) bond.
2ai 1 Insist on C–OH bond.
Do not allow 2-hydroxypropane.
1
propan-2-ol
2 a ii nucleophilic substitution 1 Both words needed for mark.
Do not allow SN1 or SN2.
2 Penalise incorrect polarity on
C–Br (M1).
If SN1, both marks possible.
2bi Elimination 1
2 b ii base OR proton acceptor 1 Do not accept nucleophile.
3ai An electron pair donor 1 Answer must refer to an electron
pair.
OR
‘Attracted’ does not equal
forms a covalent or co-ordinate or dative bond by
‘donated’.
donating a pair of electrons.
3 a ii Penalise M1, if covalent NaOH is
used.
Penalise M2 for formal charge on
C or incorrect partial charges.
M1 must show an arrow from the lone pair of
electrons on the oxygen atom of the negatively Penalise once only for a line and
charged hydroxide ion to the central C atom. 1 two dots to show a bond.

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 13 Halogenoalkanes
AQA Chemistry Exam-style mark scheme

Question
Answer Marks Guidance
number
M2 must show the movement of a pair of electrons Max 1 mark for the wrong
from the C–Br bond to the Br atom. Mark M2 reactant.
independently.
1 Award 1 mark only for C–Br bond
breakage, if an SN1 mechanism
is used.
Do not penalise the use of ‘sticks’.
3bi Structure of the tertiary carbocation (CH3)3C or 1 Insist on a full positive charge on
drawn out the central C atom.
Penalise a bond to the positive
charge.
3 b ii Tertiary carbocation / carbonium ion (from 2-bromo- 1 Ignore reference to the alleged
2-methylpropane) is more stable (than the primary relative stability of
carbocation / carbonium ion). halogenoalkanes.
OR
Primary carbocation / carbonium ion (from 2-bromo-
2-methylpropane) is less stable (than the tertiary
carbocation / carbonium ion).
4ai
1

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 13 Halogenoalkanes
AQA Chemistry Exam-style mark scheme

Question
Answer Marks Guidance
number
4 a ii 1

1
2-chloro-2-methylbutane

4bi Elimination 1

4 b ii Alkene A and B (in any order) 1

1
Alkene C

4 b iii Alkene C has a CC bond, but does not have two 1
different groups attached to the end carbon atom.
5 Mr of CF3CHBrCl  197.4 1

3.948 ´ 10–4 ´ 103

Moles of halothane 
197.4
 0.002 1

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 13 Halogenoalkanes
AQA Chemistry Exam-style mark scheme

Question
Answer Marks Guidance
number
Number of molecules  0.002  6.02  1023
1
 1.204  1021

(1.204 ´ 1021 ´ 500 ´ 10–6 )

Molecules in 500 cm3 
150 1
 4.01  1015
6a 2-bromobutane 1
6b Elimination 1
Curly arrow from lone pair on oxygen of hydroxide
ion to H atom on correct C–H adjacent to C–Br. 1
Curly arrow from single bond of adjacent C–H to
adjacent single bond C–C. 1
Curly arrow from C–Br bond to side of Br atom. 1
6ci Structural isomers have the same molecular 1
formula, but different structural formulas / different
structures.
6 c ii Correct structure for but-1-ene: 1

7ai M1 Elimination 1 For M1, accept ‘Base elimination’,

but no other prefix.
1
Penalise M2, if covalent KOH.
1
Penalise M4 for formal charge on
1
C of C–Br OR incorrect partial
M2 must show an arrow from the lone pair on the charges on C–Br.
oxygen of a negatively-charged hydroxide ion to a
Ignore other partial charges.
correct H atom.
Penalise once only in any part of
M3 must show an arrow from a C–H bond adjacent
the mechanism for a line and two
to the C–Br bond towards the appropriate C–C
dots to show a bond.
bond. Only award if a reasonable attempt has been
made at the attack on the H atom of the appropriate Max any 2 of 3 marks for the
adjacent C–H. mechanism for wrong reactant (or
wrong product if shown).
M4 is independent, provided it is from their original
molecule.
Award full marks for an E1 mechanism in which M3
is on the correct carbocation.
7 a ii Structure for pent-1-ene: 1 Penalise C3H7.
CH3CH2CH2CHCH2

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 13 Halogenoalkanes
AQA Chemistry Exam-style mark scheme

Question
Answer Marks Guidance
number
7b M1 Electrophilic addition 1 For M1, both words required.
1 For the mechanism
1 M2 Ignore the partial negative
charge on the double bond.
1
M3 Penalise partial charges on
1
the Br–Br bond, if wrong way and
penalise formal charges.
M2 must show an arrow from the double bond Penalise once, only in any part of
towards the Br atom of the Br–Br molecule. the mechanism for a line and two
M3 must show the breaking of the Br–Br bond. dots to show a bond.
M4 is for the structure of the tertiary carbocation, Max any 3 of 4 marks for the
with Br on the correct carbon atom. mechanism for wrong organic
reactant or wrong organic produce
M5 must show an arrow from the lone pair of (if shown) or primary carbocation.
electrons on the negatively charged bromide ion
towards the positively charged carbon atom. If HBr is used, max 2 marks for
the mechanism.

7c M1 Nucleophilic substitution 1 For M1, both words required.

1 Penalise M2 if NH3 is negatively
charged.
1
Penalise M3 for formal charge on
1
C or incorrect partial charges.
1
The second mole of ammonia is
M2 must show an arrow from the lone pair of not essential for M5; therefore
electrons on the nitrogen atom of an ammonia ignore any species there.
molecule to the C atom.
Penalise once only for a line and
M3 must show the movement of a pair of electrons two dots to show a bond.
from the C–Br bond to the Br atom. M3 is
independent, provided it is from the original Max any 3 of 4 marks for the
molecule. mechanism for wrong organic
reactant (or wrong organic product
M4 is for the structure of the alkylammonium ion, if shown).
which could be a condensed formula. A positive
charge must be shown on / close to the N atom. Accept the correct use of ‘sticks’.

M5 is for an arrow from the N–H bond to the N atom.

Award full marks for an SN1 mechanism, in which
M2 is the attack of the ammonia on the intermediate
carbocation.

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