1.

(i)

Cl2 2 Cl (1)
CH4 + Cl CH3 + HCl (1)
CH3 + Cl2 CH3 Cl + Cl (1)
Cl + Cl Cl2
or

CH3 + CH3 C2H6

or

CH3 + Cl CH3Cl

etc.(1)
(ii)

Initiation (1)

(iii)

Suggestion

Use excess methane or limit the amount of Cl2 (1)

Reason

Idea of - to minimise multiple substitutions (1)

or to minimise or prevent further reaction or

substitution
(of CH3Cl)
or more chance of Cl colliding with CH4 or methane
[7]

2.
(a)

Correct structure for CF2BrCF2Br drawn out

(penalise Fl for fluorine)

(b)

(i)

2bromo2chloro1,1,1trifluoroethane
OR 1bromo1chloro2,2,2trifluoroethane
(insist on all numbers, but do not penalise failure to
use alphabet)
(accept flourine and cloro in this instance)

(ii)

197.4 only
(ignore units)

(iii)

(57/197.4 100) = 28.9% OR 28.88%

(credit the correct answer independently in part
(d)(iii), even if (d)(ii) is blank or incorrectly
calculated, but mark consequential on part (d)
(ii), if part (d)(ii) is incorrectly calculated,
accepting answers to 3sf or 4sf only)
(penalise 29% if it appears alone, but not if it
follows a correct answer)
(do not insist on the % sign being given)
(the percentage sign is not essential here, but
penalise the use of units e.g. grams)
[4]

C H
3.

(a)

(b)

C H

C H

Br

Equation
(C H 3 )2 C H -C H -C H

(1)

+ N aO H

(C H 3 )2 C H -C H -C H

Br

+ N aB r
(1 )

O H

Type of reaction

hydrolisis or nucleophilic

substitution (1)

Mechanism

C H (C H 3) 2

H O :
(1 )

(c)

B r

CH

C H (C H 3 ) 2

H
H O

(1 )

C H

Type of reaction

elimination (1)

Role of reagent

base (1)

Structural formula of alkene 1

:B r

Structural formula of alkene 2

(CH3)2C=CHCH3 (1)

(CH3)2CHCH=CH2 (1)
[9]

4.

(a)

(b)

(i)

UV light OR sunlight OR T 450C (1)

NOT high T

(ii)

(free) radical substitution (1)

(iii)

CCl4 (1) OR named

(i)

CH3Cl + KCN CH3CN + KCl (1)

CN

(c)

Cl

(ii)

nucleophilic substitution (1)

(iii)

CBr bond is weaker (than CCl bond)

OR CBr bond enthalpy is less than CCl (1)
Ignore electronegativity

(i)

C Cl OR CCl is polar (1) OR C atom is electron deficient / +

(ii)

methylamine (1) only

(iii)

SN1 scores full marks

(1 )

C H

..
N H

(1 )

Cl

H 3C
N
(1 )
H

A llo w o n N H 3
p e n a lis e o n N H 3

..
N H

(C H 3 N H

+ N H

(1 ) s tru c tu re
H

s e c o n d m o le
n o t e s s e n tia l
3

)
[12]

2.8 test ms
1.

1(-)bromobutane
correct structure for 1-bromo-2-methylpropane
(CC bonds must be clear where drawn)
[2]

2.

(i)

2-bromo-3-methylbutane
correct spelling each of bromo, methyl and butane (1)
for numbers 2 & 3 either order (1)

(ii)

compounds with the same molecular formula / compounds or molecules

with the same number and type of atoms
not atoms or elements instead of compounds (1)
different structural formulae / different arrangement of atoms / different
structures / different graphical (displayed) formulae / functional groups in
different places (1)

(iii)

CH

CH

Br
3

accept CH3CH2.... (1)

[5]

3.

(a)

(i)

(Free) radical substitution

(Both words needed)

(ii)

M1 initiation ONLY
M2 ultra-violet light OR sunlight OR 1000C T 450C
(Ignore reference to temperature if included with
uv light)
(Penalise high temperature for M2)

(iii)

H C2H6
2C
3
(OR CH3CH3 as alternative to C2H6)

(iv)

CH3Br + Br2 CH2Br2 + HBr

(b)

(i)

Electron pair donor

OR species with an electron pair able to form a covalent bond.

(ii)

Methylamine
(Credit aminomethane)

(iii)
H
CH
:N H

Br

CH

M 3 s tru c tu re

[ :N H 3 ] (n o t e s s e n tia l)
M1 arrow to show breakage of C Br bond
M2 arrow from lone pair on N of NH3 to form bond with C

M4 arrow from bond of N H to N atom of CH3 N H 3

(Ignore partial charges on haloalkane but
penalise if incorrect)

(Accept CH 3 N H 3 for M3)

(Full credit for carbocation mechanism; M1 for
C Br bond breakage and M2 for lone pair
attack on carbocation)
(Second mole of ammonia not essential to
mechanism for full credit)
[11]

4.

(a)

C 22.24/12 = 1.85 H 3.71/1 = 3.71 Br 74.05/79.9 = 0.927 (1)

ratio C:H:Br = 2:4:1 C2H4Br (1)
empirical mass = 107.9 mol formula = 215.8/107.9 C2H4Br =
C4H8Br2 (1)
must use % to justify answer
or
C (22.24/100) 215.8 = 47.99 i.e. 48/12 = 4 carbon atoms (1)
H (3.71/100) 215.8 = 8.01 i.e. 8/1 = 8 hydrogen atoms (1)
Br (74.05/100) 215.8 = 159.8 i.e. 159.8/79.9 = 2 bromine atoms (1)
or
C (48/215.8) 100 = 22.24% (1)
H (8/215.8) 100 = 3.71 % (1)
Br (159.8/215.8) 100 = 74.05% (1)

(b)

any two pairs of marks

1,1-dibromo-(2-)methylpropane (1)
graphical formula to suit (CH3)2CHCHBr2 (1)
1,2-dibromo-(2-)methylpropane (1)
graphical formula to suit (CH3)2C(Br)CH2Br (1)
1,3-dibromo-(2)-methylpropane (1)
graphical formula to suit BrCH2CH(CH3)CH2Br (1)
allow unambiguous names
mark name and structure independently
accept order of bromo / methyl reversed

penalise once for each of

numbering from wrong end and di in dibromo omitted
(c)

(d)

(i)

alcoholic/ethanolic solution (not just alcohol must be solvent) (1)

structure to suit CH3CH=CH2 (1)

(ii)

aqueous solution (not water alone, unless solvent penalised in (i))

(1)
structure to suit CH3CH(OH)CH3 (1)

(i)

cyanide ion / CN / NC

(ii)

nucleophilic substitution / SNI / SN2 (1)

(iii)

CH3CH(Br)CH3 + KCN CH3CH(CN)CH3 + KBr / ionic version

(1)
(condone missing brackets)

(iv)

structure to suit CH3CH(CN)CH3 (with CN bond shown as a

triple bond) (1)

not nitrile ion (1)

1
[15]

5.

Ml curly arrow from lone pair on oxygen of hydroxide ion to H atom on

C-H
adjacent to C-Br
M2 curly arrow from single bond of adjacent C-H to adjacent single bond
C-C
(only credit M2 if Ml is being attempted to
correct H atom)
M3 curly arrow from C-Br bond to side of Br atom

6.

(a)

dichlorodifluoromethane / accept halogens reversed (1)

ignore number l in name; penalise other numbers
ignore hyphens and gaps

(b)

appropriate tetrahedral shape (1)

explains that tetrahedral shape due to repulsion between
(four bonding) pairs of electrons not pairs of atoms repelling (1)
repulsion unequal due to bonds to different atoms / covalent radii /
bond lengths / different electronegativity / dipoles (1)

(c)

CCl bond weaker / longer than C-F bond / CF bond is stronger (1)
[5]

7.

(a)

(CH3)2 CH CH2CH2Br (1)

1-bromo-3-methylbutane (1)
CH3 CH2CH (CH3) CH2Br (1)
1-bromo-2-methylbutane (1)
(CH3)2CH CHBr CH3 (1)
2 bromo-3-methylbutane (1)
6

(b)

two bromine isotopes (1)

11 79

C5H

81

Br = 150 and C5H11 Br = 152 (1)

relative abundances approximately equal (1)

[9]

2.8 EXTRA QUESTIONS MS

1.

(i)

Cl2 2Cl / Cl2 Cl (1)

(ii)

Cl+ C6H5CH3 C6H5CH2 + HCl (1)

C6H5CH2 + Cl2 Cl + C6H5CH2Cl (1)

(iii)

C6H5CHCl2 / C6H5CCl3 / C6H5 CHCHC6 H5 /

other correct possible answer (1)
[4]

2.

(a)

(i)

(free)radical substitution
(both words required for the mark)

(ii)

uv light OR sunlight OR high temperature OR 150 C to 500 C

(iii)

Propagation
(ignore chain, first, second in front of the
word propagation)

(iv)

Termination
CH2CH3 + Br

CH3CH2Br
OR 2CH2CH3

C4H10
(penalise if radical dot is obviously on CH3, but not
otherwise)
(penalise C2H5)

(credit 2Br

Br2)

(ignore chain in front of the word

termination)
(b)

(i)

Fractional distillation OR fractionation

(credit gasliquid chromatography, GLC)

(ii)

CH3CH3 + 6Br2 C2Br6 + 6HBr

(credit C2H6 for ethane)
[7]

3.

(a)

(i)

(free) radical substitution

(both words required for the mark)
initiation Cl2 2Cl
(credit correct half arrows, but penalise double headed arrows)
first propagation CH3Cl + Cl CH2Cl + HCl
second propagation CH2Cl + Cl2 CH2Cl2 + Cl
(penalise the absence of dots on radicals once only)
(penalise radical dot on Cl of CH2Cl once only)

(b)

(ii)

CH3Cl + Cl2 CH2Cl2 + HCl

(penalise if any radicals appear in this equation)

M1:

mol C = 10.1/12.0 and mol Cl = 89.9/35.5

M2:

Ratio 0.842 : 2.53 OR 1: 3 OR CCl3

M3:
237.0/Mr of CCl3 = 237.0/118.5 = 2 Therefore C2Cl6
(correct answer gains full credit)
OR
M1:

237.0 10.1/100 and 237 89.9/100

M2:

Ratio 23.9/12.0 : 213/35.5 OR 2 : 6

M3:
C2Cl6
(correct answer gains full credit)
(c)

any two from CHBr3 or CBr4 or C2H2Br4 (or CHBr2CHBr2) or C2Br6

(or CBr3CBr3)
(ignore HBr or H2)
(ignore equations and ignore names when given in addition to formulae)
(penalise names alone)
[10]

4.

(a)

(i)

substitution or hydrolysis (1)

nucleophile (1)

H 3C

(ii)

H O :
(1 )

C H (C H 3 )
B r (1 )

C H 2C H

CH

H O

C H (C H 3 ) 2

C H 2C H

(1 )
or

H 3C

C H (C H 3 )
C

B r

C H 2C H

(b)

(i)

H 3C

H O :

+
C

C H (C H 3 ) 2

C H 2C H

Type of reaction

elimination (1)

Role of reagent

base or proton acceptor (1)

(ii)

Structure of the alkene

(CH3)2C=C(CH3)CH2CH3 (1)

Mechanism

(1 )
H
(C H 3 ) 2C
C
H 3C

(1 )

(C H 3 ) 2C

Br

C H 2C H

:O H

Br

H
(1 )

:O H
C H 2C H

+C
CH

o r (C H 3 ) 2C
H 3C

(iii)

C H 2C H

Structure of second alkene

(CH3)2CHC(CH3)=CHCH3 (1)

Name

3,4-dimethylpent-2-ene (1)

Structure of third alkene

(CH3)2CHC(C2H5)=CH2 (1)

Name

2-ethyl-3-methylbut-1-ene(1)
[15]

5.

(i)

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)
M2 curly arrow from the middle of the CH bond to the middle of
the CC bond.
(only credit this mark if the arrow originates from
the correct
CH bond and if an attempt has been made at M1)
M3 curly arrow from the middle of the CBr bond
towards/alongside
the Br atom.
(credit M3 independently unless the bond breaking is
contradicted by an additional arrow)
(penalise M3 curly arrow if the CBr has a formal positive
charge)
(ignore partial charges on the CBr bond, but penalise if
incorrect)
(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 an incorrect

haloalkane)
(ignore products)

(ii)

Haloalkane/C2H5Br is made from ethane

OR haloalkane is not (readily) available
OR haloalkane is expensive
OR it is (too) expensive/costly
OR (reaction) yield is too low/poor
OR it is too slow
OR a valid reference to nucleophilic substitution/alcohol formation
occurring as an alternative reaction.
(ignore references to temperature or to energy
consumption)
(do not credit statements which refer to the idea that
this route
is not chosen, because industry chooses another route
e.g. cracking)
[4]

6.
(i)

M1: potassium cyanide OR KCN OR sodium Cyanide OR NaCN;

(ignore conditions - dissolved in (aq) or (alc) or
KOH(aq) all work) (penalise HCN)
M2: propanenitrile;
(credit propan-1-nitrile OR propan nitrile, but
not propanitrile)

(ii)

M1: ammonia OR NH3;

(If formula is written, insist that it is correct)
(ignore conditions, but penalise acidic)
M2: ethylamine;
(credit aminoethane)

(iii)

M1: curly arrow from lone pair on nitrogen of (correct formula for)
ammonia towards/alongside C atom of C-Br;
(penalise M1 if formula of ammonia is wrong or
has a negative charge or has no lone pair or
arrow is from negative charge)
M2: curly arrow from C-Br bond towards/alongside side Br atom;
(credit M2 independently)
(penalise M2 if formal positive charge on C
atom of C-Br)
M3: correct structure of the ethylammonium ion;
(credit the structure drawn out with all four
bonds around the nitrogen atom OR written as
+
+
C2H5NH3 OR CH3CH2NH3 )

M4: curly arrow from the middle of one of the H-N bonds towards
the
positive N atom;
(possible to credit M4 on an incorrect
ethylammonium ion with no positive charge)
(ignore use of ammonia or bromide ion etc. to
remove proton from ethylammonium ion)
(If the wrong haloalkane is used, award MAX. 3
marks for the mechanism) (If SN 1 mechanism is
used, give full credit in which M1 is for a curly
arrow from the lone pair of the N atom of
(correct formula for) ammonia
towards/alongside the positive carbon atom of
+
CH3CH2 )
[8]

C H
7.

(a)

CH

C H

Br

C H

CH

C H

or

C H 3 C H B rC H (C H 3 )2

(1 )

H 3C
(b)

(i)

or

CH

C H 3C H

C (C H 3)2

(1 )
(ii)

(nucleophilic) elimination

(1 )
(1 )
C H

(c)

:O H

CH

(1 )

Br

CH

CH

o r v ia

C H 3 C H C H (C H 3 )2

3methylbut1ene (1)
[7]

8.

(i)

Mechanism:


CH

H O :
3

CH
Cl

(1 )

M 1

C H
(1 )

CH

CH

..
C H 3+ Cl

O H

M 2

C re d it M 1 fo r

CH

H O :
3

CH
+

C H

M1 and M2 independent
Curly arrows must be from a bond or a lone pair
Do not penalise sticks
O H precedes (penalise this
Penalise M1 if N a
once)
Penalise incorrect + for M2
Penalise + on C atom for M2
Only allow M1 for incorrect haloalkane
Role of the hydroxide ion: nucleophile (1)
electron pair donor
lone pair donor
NOT nucleophilic substitution

(ii)

Mechanism:

H O : (1 ) M 1
M 2
H ( 1 )H
H

C H 3
(1 )
C l
M 3

H 2C

CH C H

..
+ C l + H 2O

H O :

C
+

C H

H
Only allow M1 and M2 for incorrect haloalkane
unless RE on (i)
+ charge on H on molecule, penalise M1
M3 independent
M2 must be to correct CC
M1 must be correct H atom
Credit M1 and M2 via carbocation mechanism
No marks after any attack of C by OH

Role of the hydroxide ion: base (1)

proton acceptor
+
accepts H
[7]

(a)

(i)

Structure:

O H
H 3C

C H

C H

(1 )

in s ist o n
C
O H bond

No credit for propan-1-ol even when named correctly

Credit propane-2-ol

Name: propan-2-ol (1)

Not 2-hydroxypropane

(ii)

Name of mechanism: nucleophilic substitution (1) (both words)

(NOT SN1 orSN2)
Mechanism:
M 1
a rro w (1 )
H 3C

B r
C H

H O :

C H

C H 3 C H (O H )C H

(1 ) a rro w fro m
( M 2 ) lo n e p a ir

penalise incorrect polarity on C-Br (M1)

Credit the arrows even if incorrect haloalkane
If SN1, both marks possible

9.

+ B r

(b)

M 1

(i)

elimination (1)

(ii)

base (1)

Br

M 2

i.e .

H O

c o rre c t c a rb o c a tio n

OR proton acceptor
NOT nucleophile (base)
[7]

10.

(a)

M1 NaOH OR KOH OR correct name

M2 aqueous or solution in water (ignore heat, reflux etc.)
(Penalise M1 for hydroxide ion alone, but mark
on and credit M2)
(Credit M2 ONLY for H2O as reagent and heat /
o

warm / T=50 to 100 C)

(NaOH(aq) scores M1 and M2 provided it is not
contradicted)
(Penalise M2 if NaOH(aq) followed by
concentrated or ethanol)
(Penalise M1 and M2 if followed by acid)
(b)

Ethanolic OR alcoholic OR CH3CH2OH / CH3OH solvent OR

aqueous ethanol/alcohol
OR higher temperature (must be comparative)
(Ignore heat or heat under reflux)
(Credit part (c) independently from part (b))
(Penalise ethanoic)
[3]

11.

(i)

2methylpropanenitrile (1)

(ii)

Reagent KCN (1)

Conditions alcoholic/aq (1)

(iii)

Name of mechanism

nucleophilic

substitution (1)

Mechanism
C H
CH

N C : [1 ]

C H

[1 ]

Br

[1 ]

CH

CN

H
+

:B r

[7]

(a)

Name of mechanism: nucleophilic substitution (1)

Mechanism:

C H
CH

(1 )

(1 )

B r

C H

:N H

(1 )

C H

H
+

H
(1 )

:N H

(w ro n g d ip o le

C
B r or C
lo s e s C
Br
m a rk )

(M 3 is fo r c o rre c t
c a r b o c a tio n - if
u se d w ro n g
h a lo g e n o a lk a n e
lo s e M 3 )

12.

B r

Marks SN1 using same points

C H

M2 requires

C H

B r

:N H

(b)

Role of potassium hydroxide: Base (1)

Mechanism:

H
C H

C
C
H

(1 )
Br
(1 )
H
:O H
(1 )

C H

(1 )

CH

M a rk E 1 u s in g s a m e p o in ts
M 2 / M 3
C H

H
:O H

[10]

13.

elimination (1)
[1]

14.

(i)

CH3 CH2 CH2 CH2 CN (1) Not C4 H9 CN

Pentanenitrile (1)

allow pentanonitrile, ignore numbers

(ii)

Nucleophilic substitution (1)

H
CH 3C H 2CH
(1 )
M 2

M 1
(1 )
Br

H
:C N

SN1 mechanism
M1 formation of carbocation including C

B r

M2 attack by :CN
allow mechanism showing Cl
If + onC lose M1
If KCN shown lose M2

If c Bs lose M1
(iii)

CF bond is strong (er) (1)

Must imply CF is stronger than CBr bond
ignore references to electronegativity, bond polarity etc.
[6]

15.

(a)

(base) elimination
(penalise other words before elimination e.g. nucleophilic)
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)
M2: curly arrow from the middle of the C-H bond to the middle
of the CC bond
(only credit this mark if the arrow originates from the correct CH
bond and if an attempt has been made at M1)
M3: curly arrow from the middle of the CBr bond towards/alongside
the Br atom
(credit M3 independently unless the bond breaking is contradicted
by an additional arrow)
(penalise curly arrow if the CBr 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)

nucleophile or electron pair donor

(penalise base)

(c)

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)
(1)butylamine
(credit 1aminobutane and butyl1amine)
(award QoL mark for correct spelling)
[8]

16.

(i)

potassium or sodium hydroxide (or other specific strong base) (1)

allow formula; not just hydroxide
in ethanolic /alcoholic solution

(independent of first mark) (1)

allow in ethanol, not just ethanol/ with ethanol

ignore references to heat / pressure

(ii)

H
H

H
H

H
H

C
C

B r

H
+ K O H

H
H

H
H

C
C

+ K B r + H 2O

structure of cyclohexene showing double bond (1)

minimum structure needed is a ring with CH2 units implied
and double bond:
do not allow KOH over arrow

equation correct overall ie balanced

allow ionic equation (1)
(iii)

elimination / dehydrohalogenation
ignore nucleophilic / electrophilic etc.
[5]

17.
(a)

(i)

CH3CH2CH2Br + KCN CH3CH2CH2CN + KBr (1)

allow C3H7Br
(ii)
(b)

allow C4H7N

nucleophilic substitution / SN2 (1)

CN or NC (1)
lone pair of electrons on C atom (1)
[4]

18.

(a)

2-bromobutane;

(b)

Elimination;
(penalise nucleophilic OR electrophilic
before the word elimination)
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)
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)
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 M2 are for correct curly arrows
on the correct carbocation)
[5]

19.

(a)

(b)

(i)

CH3Cl + 2Cl2 CHCl3 + 2HCl (1)

(ii)

step in which radicals are used and formed (1)

(iii)

CH3Cl + Cl CH2Cl + HCl (1)

(iv)

CHCl2 + Cl2 CHCl3 + Cl

Equation
Mecanism

CH3Cl + 2NH3 CH3NH2 + NH4Cl (1)

(1 )
H 3N :

C H

Cl

CH

(1 )

(1 )

(1 )
+

H
:N H

[9]

CH4 + Cl2 CH3Cl + HCl (1)

20.

Initiation: Cl2 2Cl. (1)

Propagation: CH4 + Cl. CH3. + HCl (1)
CH . + Cl CH Cl + Cl. (1)
3

Termination: Cl. + Cl. Cl2 (1)

or CH3. + CH3. C2H6
[5]

21.

Reaction 5

NH3 (1)
For Reaction 4; credit dil H2SO4 OR H2SO4(aq)
OR HCl (aq) but NOT steam and NOT
NaOH(aq)
[1]

22.

nucleophilic substitution
(both words needed)
Mechanism M1 curly arrow from lone pair on oxygen of hydroxide
ion to C atom of C-Br
Mechanism M2 curly arrow from C-Br bond to side of Br atom
(a possible repeat error here from Question 4a)
(award a maximum of one mark for the wrong
haloalkane)
(credit an SNl mechanism in which Ml will be a
curly arrow from the lone pair on oxygen of the
hydroxide ion to the correct positive carbon
atom)
Y is susceptible to attack by hydroxide ions for one of the following
reasons
o
o
o

the C-Br bond is polar

the carbon atom is partially positive (or shown as such)
the carbon atom is electron deficient
[4]

23.

(a)

Reaction 2: NaOH OR KOH (1) M1

alcohol (ic) OR ethanol (ic)(1)
M2
ignore heat
Condition mark linked to correct reagent but

award M2 if OH or base or alkali mentioned

2
(b)

Mechanism:

H O :

(1 )M 1
M 2
H (1 )H
C

H (
(1 )
M 3
Cl

H 2C

C H

..
+ H 2O + C L

Award M3 ( C
C l ) independently
M1 and M2 must be to / from correct places
E1 mechanism possible in which M2
H
H

H
Name: of mechanism = elimination (1)
NOT dehydrohalogenation
Ignore base OR nucleophilic before
elimination
Reason: Reaction 2 has (very) low yield (1)
QoL OR chloroethane has to be made (from
ethane)
OR chloroethane is expensive
OR chloroethane is not redily available
[7]

24.

(a)

Alcohol: Reaction = Substitution (/ hydrolysis) (1)

Ignore reference to nucleophilic, but electrophilic give zero

Alcohol: Role = nucleophile (/ lone pair donor) (1)

Alkene: reaction = elimination (1)
Ignore ref to nucleophilic or electrophilic

Alkene: base (/ proton acceptor) (1)

(b)

Alcohol = butan-2-ol (1)

Not 2-hydroxybutane or but-2-ol

Appropriate structure for CH3CH(OH) CH2CH3 (1)

Brackets not essential

SN2 version

SN1 version

C Br bond is polar

Lone pair of OH
Attacks the C

CBr bond is polar (1)

CBr bond breaks (1)
forming carbocation / carbonium ion (1)

M1 can be scored from a diagram, M2 and M3 from written

explanation only

[9]

25.

(i)

2-chloro(-2-)methylpropane / (2)methyl 2 chloropropane (1)

(ii)

appropriate unambiguous formula for either but-1-ene or but-2-ene

(1)
appropriate unambiguous formula for the remaining structural
isomer
allow 1 mark if candidate draws cis and trans but-2-ene (1)

(iii)

unambiguous structure for 2-methylpropan-1-ol may be

from mechanism (1)
curly arrow / attack by OH
charge only (1)

curly arrow from lone pair or

do not allow if Na -OH

curly arrow from bond to Cl / dipole shown on
C-Cl bond / intermediate showing 3 full and 2 partial bonds to C (1)

loss of Cl

not allowed

NaCl or Na :Cl (1)

if SN1 mechanism given:

first mark as above - independent
second mark for correct carbocation formed including curly
S+
S
arrow from C to Cl or C Cl
third mark for hydroxide attack as above
final mark not available (wrong mechanism)
penalise missing proton once only
[7]

26.

(1 )

Br
C H 3C H
H O

(1 )

C
CH

CH

(1 )

O H
b a se
(1 )

C H 3C H
H
H O

(1 )

O H
n u c le o p h ile
(1 )
CH 3CH=C(CH3)2 (1)
CH3CH2C(OH)( CH3)2 (1)
2-methylbutan-2-ol (1)

2-methylbut-2-ene (1)
+

CH

C
(1)

CH

also loss of H from CH3 (1)

or

Br

C H 3C H
H
H O

C
(1 )

CH

CH
3

C H 3C H

C = C H
C H

(1 )

(1)
2 - m e th y lb u t - l - e n e

(1 )
14
[14]