15 Alcohols

AQA Chemistry Exam-style mark scheme

Question
Answer Marks Guidance
number
1a Displayed formula for butan-2-ol M1 displayed formula must have all
1 bonds drawn out, including the O–H.
but ignore angles.
Penalise ‘sticks’.
M2 structure must be clearly
identifiable as 2-methylpropan-2-ol and
may be drawn in a variety of ways.
Alcohol X is 1
M3 must be correct name, but ignore
structures.

Alcohol Y is named (2)-methylpropan-1-ol 1

ONLY.
1b Balanced equation Or multiples for M1 and M3
1
C6H12O6 → CH3CH2CH2CH2OH  2CO2  H2O In M1 and M3, penalise use of C4H10O
(or C4H9OH) or butan-2-ol once only.

Any one from: For M2, do not accept simply ‘oxygen’

1
or ‘air’ alone.
 excess amount of oxygen or air
Ignore reference to ‘temperature’.
 OR good mixing of the fuel and air /
oxygen. In M4, ignore references to ‘carbon
1
neutral’.
CH3CH2CH2CH2OH  6O2 → 4CO2  5H2O
(or C4H9OH) Ignore ‘sugar’ and ‘glucose’.

A biofuel is a fuel produced from (renewable)

biological resources OR (renewable) resources 1
from a specified plant(s) / fruit(s) / tree(s).
1c Butan-1-ol is a primary or 1° alcohol. M2 and M3 displayed formula must
1 have all bonds drawn out, including the
Displayed formula (ONLY) for butanal
O–H, but ignore angles.
CH3CH2CH2CHO. 1
If butanal and butanoic acid formulae
Displayed formula (ONLY) for butanoic acid 1
are both correctly given but not
CH3CH2CH2COOH.
1 displayed, credit one mark out of two.
Oxidation (oxidised) OR Redox
1 Both colours required for M5. Ignore
orange to green states.
2ai C6H12O6  2C2H5OH  2CO2 1

2 a ii Fermentation 1
2b Elimination 1 Penalise ‘sticks’ once only.
Structure of protonated alcohol 1

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 15 Alcohols
AQA Chemistry Exam-style mark scheme

Question
Answer Marks Guidance
number

1
For the mechanism, award one mark for each 1
of the following:
 arrow to show breakage of C–O bond on
protonated alcohol
 structure of carbocation
 arrow from correct C–H bond on
carbocation.
3a CH2O 1
3b Penalise C2H6O.
For M2 and M3:
C6H12O6 → 2 CH3CH2OH  2 CO2 1
Ignore ‘aqueous’.
Either order:
 (enzymes from) yeast or zymase Ignore ‘anaerobic / absence of
1
oxygen’.
 25 °C ≤ T ≤ 42 °C OR 298 K ≤ T ≤ 315 K. 1
Ignore ‘controlled pH’.
Ignore ‘warm’.
3ci Displayed formula for CH3COOH. 1

3 c ii O2  4H  4e− → 2H2O 1 Ignore state symbols.

Negative charge on electron not
essential.

3 c iii CH3CH2OH  H2O → CH3COOH  4H  4e– 1 Ignore state symbols.

(C2H6O or C2H5OH) Negative charge on electron not
essential.

3 c iv Acidified potassium or sodium dichromate For M1, it must be a whole reagent

and / or correct formulae.
OR H2SO4 / K2Cr2O7 or H / K2Cr2O7, etc. 1
If oxidation state given in name, it must
OR correct combination of formula and name be correct, but mark on from an
orange to green (requires an attempt at M1) 1 incorrect attempt at a correct reagent.
Possible alternative:
acidified potassium manganate(VII) OR KMnO4 Other alternatives will be accepted, but
/ H2SO4 M2 is dependent on M1 in every case.

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 15 Alcohols
AQA Chemistry Exam-style mark scheme

Question
Answer Marks Guidance
number
purple to colourless M2 requires an attempt at a correct
reagent for M1.
Ignore reference to states.
3di An activity which has no net / overall carbon 1 The idea that the carbon / CO2 given
emissions to the atmosphere / air out equals the carbon / CO2 that was
taken in from the atmosphere / air.
OR
Answer must refer to the atmosphere
An activity which has no net / overall (annual)
or air.
greenhouse gas emissions to the atmosphere /
air.
OR
There is no change in the total amount of
carbon dioxide / carbon / greenhouse gas
present in the atmosphere / air.
3 d ii Renewable / sustainable ONLY 1 Ignore references to global warming or
greenhouse gases.
3 d iii Any one statement about this process from: 1
 Subject to weather / climate
 Depletes food supply OR the land use for
(specified) food
 Requires use of / uses more fossil fuels
 Not carbon-neutral OR CO2 produced
during a named process (e.g. harvest,
transport, etc.)
 Slow process / slow rate of reaction / takes
a long time (to grow crops)
 This route leads to the production of a
mixture of water and ethanol / impure
ethanol that requires separation / further
processing.
4a Sodium or potassium hydroxide / NaOH / KOH 1 Mark on to M2 from hydroxide ion.
Warm / heat / reflux and aqueous or (aq) or 1 Ignore OH– if KOH / OH–.
water
M2 depends on correct M1.
Nucleophilic substitution 1
For M2, ignore ‘dilute’.
For M2, penalise T > 100 °C.
Acidified KOH/NaOH or H2SO4 with
KOH/NaOH loses M1 and M2.
M4 must show an arrow from the lone pair of For M3, both words required
1
electrons on the oxygen atom of the negatively Penalise M4, if covalent NaOH / KOH
charged hydroxide ion to the C atom. is used.
M5 must show the movement of a pair of 1
Penalise one mark from M4 or M5, if
electrons from the C–Br bond to the Br atom. half-headed arrows are used.
Mark M5 independently, provided it is from 1
their original molecule. Penalise M5 for formal charge on C of
the C–Br or incorrect partial charges

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 15 Alcohols
AQA Chemistry Exam-style mark scheme

Question
Answer Marks Guidance
number
One statement from: on C–Br.
 the yield is (very) low / not a high yield OR Penalise once only for a line and two
elimination occurs/ethene formed dots to show a bond.
 the rate of reaction slow For M4 and M5, maximum 1 of 2
 bromoethane has to be manufactured / marks if wrong reactant is used.
made first Penalise M5 if an extra arrow is drawn
 bromoethane is expensive. from the Br of the C–Br bond to, e.g.
K
For M4 and M5, award full marks for
an SN1 mechanism.
For M6, ignore references to other
costs and expenses.
4b Concentrated phosphoric acid / concentrated 1 Answers in any order.
H3PO4 OR concentrated sulfuric acid /
Ignore reference to support medium in
concentrated H2SO4
M1.
Hydration or (electrophilic) addition 1
Any two from: 2
 Excess ethane
OR excess steam
OR remove the ethanol as it forms
OR recycle the ethane.
 Specified pressure
50 atm ≤ P ≤ 100 atm
OR 5000 kPa ≤ P ≤ 10 000 kPa
OR 5 MPa ≤ P ≤ 10 MPa.
 High temperature, unless they give a value
that is not in the ranges given here:
OR 300 °C ≤ T ≤ 600 °C
OR 570 K ≤ T ≤ 870 K.
5a Pentan-2-one 1 ONLY but ignore absence of hyphens.
5b Functional group (isomerism) 1 Both words needed.
5ci 1 The group needs to be CHOHCH3, but
do not penalise poor C–C bonds or
absence of brackets around OH.
Trigonal planar structure not essential.

5 c ii Restricted rotation about the CC 1

OR
No (free) rotation about the CC.
5d 3 If M1 is blank, CE  0.

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 15 Alcohols
AQA Chemistry Exam-style mark scheme

Question
Answer Marks Guidance
number
M1 Tollens’ reagent M1 Fehling’s Check the partial reagents listed and if
solution / M1 has a totally incorrect reagent, CE
(Credit ammoniacal
Benedict’s  0.
silver nitrate OR a
description of (Penalise Cu2(aq) mark on from incomplete formulae or
making Tollens’.) or CuSO4, but incorrect oxidation state
mark M2 and M3.)
(Do not credit Ag, M2 turns colourless
AgNO3 or M3 stays purple / no (observed)
[Ag(NH3)2] or ‘the change / no
silver mirror test’ on
their own, but mark reaction
M2 and M3.) In all cases for M3
M2 silver mirror M2 red solid / Ignore ‘nothing happens’
precipitate
OR black solid or Ignore ‘no observation’.
black precipitate (Credit orange or
brown solid.)
M3 stays colourless M3 stays blue.
OR no observed OR no observed
change / no change / no
reaction. reaction.

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