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PMT

1
...


(i)

(ii)

Any two realistic fragments,
e
...
CH3+: 15; C2H5+: 29; C3H7+: 43; C4H9+: 57; OH+: 17, etc
...


2

breathalysers/monitoring of air pollution, MOT emission testing, etc
...


Availability of starting materials:
availability
sugar is renewable because it can be grown (1)
ethane is finite because it is obtained by processing of crude oil (1)
energy:
fermentation: energy is required for distillation/
hydration: energy is required to generate steam (1)
atom economy and waste products:
atom economy for fermentation < atom economy hydration (1)
In fermentation, CO2 is produced in addition to ethanol/ethanol is
not the only product (1)
In hydration, ethanol is the only product/hydration is an addition
reaction (1)
Atom economy of fermentation could be increased by finding a use
CO2 (1)
Atom economy linked to a chemical equation to show that hydration
has 100% atom economy/fermentation has 51% atom economy (1) 7max
[7]

PMT

4
...


(ii)

balanced equation
C6H12O6 (aq) → 2C2H5OH(l) or (aq) + 2CO2(g)
state symbols can be awarded only if equation shows C6H12O6 ,
C2H5OH and CO2
anaerobic, aqueous, temp range 25 − 40°C/warm to just above room temp

1
2

(iii)

no more bubbles/gas/CO2

1

(i)

1

[5]

6
...


O

...


CH3 H
H

H

step 3
H

C

C


...


...


CH3CH(OH)CH3 + 4½O2 → 3CO2 + 4H2O /C3H8O
(1 mark if correct formula for all four chemicals and 1 mark for
correct balancing)
[2]

8
...

H

H
C

C

C
H

C2H5

H

H
C

H3C

H

H3C
C

CH3

H

C
CH3

Minimum − must display/show C=C
[3]

10
...


(a)

(i)

1
Cl

(ii)

H2SO4/Al2O3/(hot) pumice/H3PO4

1

(H2SO4(aq) or dil H2SO4 loses the mark)
(iii)

1
OH

+ H 2O
C6H11OH / C6H12O → C6H10 + H2O
(b)

(i)

1
OH

OH

also allow

OH

Cl

diol

Cl-alcohol

PMT

(ii)

2

from the diol allow

from the Cl-alcohol allow

Cl

OH

[6]

12
...
= bonds/forces/attractions between molecules

1
1

(ii)

type of intermolecular bond = hydrogen bond

1

dipoles on both O-H bonds

1

H-bond shown as a ‘dashed bond’

1

H
H

C

H

H

C

δ–
O

H
δ+
H

H

H

C

H

δ–
O

C

H

H
δ+

(iii)

H

(The boiling point of glycerol will be higher than ethanol because there are)
more OH groups ∴ more H-bonds

1
[6]

13
...


(i)

Cr2O72-

H+

2

(ii)
compound E

compound F

H

H3C
C

C
CH2

H3C CH2 CH2

H

H3C

2[O]

C
OH

H2 O

COOH

H3C CH2 CH2

C 7 H 14 O

+

C

C 7 H 14 O2







3
(iii)

carboxylic acid would have an absorption between
1680 – 1750 cm-1 /1700 cm-1 or 2500 – 3300 cm-1
...


(a)

(i)

H2SO4 – any mention of (aq) loses the mark

1

(ii)

any correct formula/structure or name for benzoic acid

1

PMT

(b)

(i)

dichromate/Cr2O72–/permanganate

1

(ii)

1
OH

O

+ [O]

H2
C

+ H2O

H2
C

OH

H2C

CH

H2C

CH2

O

H2C

C

H2C

CH2

+ H2O

+ [O]
C
H2

C6H12O

C
H2

+ [O]

C6H10O

+ H2O

[4]

16
...

require at least one ‘wedge’ bond or one
‘dotted’ bond
(ii)

108 − 111°

1

(iii)

volatile/low boiling/gas/non-toxic/non-flammable/unreactive/liquefied under
pressure/inert

1

homolytic = bonded pair split equally/ each retains 1 electron

1

fission = bond breaking

1

(v)

C-Cl (no mark) because it is the weaker bond

1

(vi)

Cl•

1

•CF3 (allow CF3•)

1

(iv)

(lack of ‘dots’ penalise once)
[8]

17
...

H

δ+
O

H

H

C

H

H

C

H

δ–
O

H

H

C

C

H

H

H

H

dipoles

1

hydrogen bond between O in one O-H
and H in the other O-H

1

lone pair from O involved in the H-bond

1
[3]

19
...


(a)

(i)

reaction 1

1

(ii)

reaction 4

1

(iii)

reaction 3

1

PMT

(b)

(i)

lone pair/electron pair donor

H3C

CH2

δ+

1

δ-

CH2

Cl

H3C

CH2

CH2

OH

+

-

Cl

...

(same formula, different structure
...


(a)

(i)

prop-2-en-1-ol CH2=CHCH2OH must show the C=C double bond

1

acrolein
O
H2C

CH

C
H

must clearly show the aldehyde group and the C=C
1
(ii)

alkene/C=C double bond

1

PMT

(b)

(i)

(ii)

acidified /H+

1

dichromate/Cr2O7 2-

1

CH2CHCH2OH/ C3H6O/ C3H5OH + [O]

CH2CHCHO/ C3H4O/
C2H3CHO + H2O
not CH2CHCOH

1
[6]

22
...

COO/CO2 without displaying the ester, they can still get 1
mark
...


Essential marks:
Order

RI>RBr>RCl /owtte

1

reason for the order

C-I bond weakest/length/C-Cl bond strongest and
mention/intermolc forces loses the mark

1

Ag+ + XAgX (solid or ppt) or an equation for
hydrolysis/using OH- or H2O

1

an equation
max = 3

Two possible methods of monitoring the reaction
Method 1

Method 2

AgNO3

AgNO3

1

Ethanol & Waterbath/
/hydroxide
temp 40 − 80°C
not heat/not bunsen

NaOH/OH-

1

& neutralise with HNO3
relative amount of
precipitation

relative rate of
precipitation

1
[6]

24
...


(a)
H H H H
H C C C C H
H H OH H

H
H C
H

CH 3 H
C H
C
OH

H

H

CH3 H

H C

C

C H

H

H

OH

3

PMT

(b)

(i)

orange to green/dark green/brown/black

1

(ii)

C4H9OH/ C4H10O + 2[O] → C3H7COOH + H2O

2

1 mark available for correct formula of the carboxylic acid
(iii)

(c)

(d)

Identify isomer 2-methylpropan-1-ol by appropriate
number/name/formula

1

CH2 has mass = 14, 14 × 4 = 56

1

∴C4H8

1

(ii)

C4H9OH → C4H8 + H2O

1

(iii)

Identify butan-2-ol by appropriate number/name/formula

1

(i)

H2SO4

1

(ii)

0
...


x

50

0
4000

3000

2000

1500

1000

500

HAVENUMBER

(c)

(i)

Ni/Pt/Rh/Pd

1

PMT

(ii)

compound B is C10H22O

1

(iii)

C10H20O + H2 → C10H22O

1
[9]

27
...


1

C2H4 + H2O → C2H5OH

1

Temp > 100 °C/Press 370 − 100 atm
continuous process

/ 6 −20 MPa/phosphoric acid catalyst/

Glucose is obtained from plants
Ethene is obtained from crude oil/cracking/fossil fuel
glucose is renewable/ethene isn’t

1
1
1
1

1 mark available for Quality of written communication…
...


(a)

(b)

(i)

C4H10

1

(ii)

C2H5O

1

(iii)

B and E

1

(iv)

A and F

1

(C4H9OH →) C4H8 + H2O

1

PMT

(c)

1

any unambiguous formula:
H

H
C

H

C
C

H

C

H

H

H

C

C

H

H
C

C

H

H

H

CH 2 CHCHCH2

H

H

H

H

C

C

C

C

H

H

CH2CHCHCH2
buta-1,3-diene
name ecf to the structure only if structure above has formula C4H6

1
[7]

29
...

H

H
OH

CH3 CH2 CH2

CH3 CH2 CH2

H

(b)

(i)

C

OH

+ Cl

H

mark for method/dividing by Ar / C, 3
...
3; Cl, 1
...


1

divide by smallest to get C2H4Cl

1

alternative method:
% of each element x 127 ÷ Ar of that
element = molecular formula, hence deduce empirical formula
(ii)

C4H8Cl2

1

PMT

(iii)

any unambiguous form of:
H H H H
H C

C

C C OH

H OH H H

1
(iv)

any unambiguous form of:

H H H H
H C

C

C

C

Cl

H Cl H H
1
ecf to (iii) provided that there are two OHs in (iii)
[9]

30

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