1.

(i)

but-1-ene (1)

(ii)

two H on one carbon of double bond (1)

(iii)

CH3CH=CHCH3 (1)

(iv)

C H

C H

C H

(1)
[4]

(a)

(b)

Name of alkene

3-methylpent-2-ene (1)

Type of stereoisomerism

geometrical or cis-trans (1)

Name of mechanism

electrophilic addition (1)

Mechanism

CH
CH 3C H
(1 )

C H

C H 3CH
C H 2C H

(1 )

Br

2.

(1 )

C H 2CH

:B r

(1 )

(c)

Structure

CH

(1 )

CH 3C H B r C H
CH 2C H
Explanation

(CH3CH2)2 CH3 or tertiary carbonium ion more

C
stable (1)
than CH3 HCH(CH3) CH2 CH3 or secondary
C
carbonium ion (1)
[10]

3.

(i)

C18H34O2 Only;
C9H17O Only;
(empirical formula is not consequential on
molecular formula)

(ii)

(An unsaturated compound) contains (at least) one double bond

OR
Contains C=C;
(must be a positive statement)

(iii)

M1: Bromine water

OR
Br2(aq)
OR
Bromine
OR
Br2;
(penalise bromide water, but mark on)
Ml: decolourised or goes colourless
OR
from brown/red/orange/yellow to colourless;
(Must be colourless not clear for M2)
(chemical error if no reagent or wrong reagent,
loses both marks) (credit KMnO 4 for M1,
(purple) to colourless for M2 (if acidified) OR
(purple) to brown/brown precipitate (if alkaline
or unspecified) (No credit for hydrogen or
iodine as reagents)
[5]

4.

(a)

(i)

Electrophilic addition
(Both words required)

(ii)

M1 the reaction to form 1-bromopropane goes via the primary

o
carbocation OR 1 carbocation

OR via CH 3 CH 2 C H 2
M2 primary carbocations are less stable than secondary
carbocations.
(Credit converse arguments for M1 and M2 i.e.
the reaction to form 2-bromopropane goes via
the secondary carbocation , M1, and secondary
carbocations are more stable than primary
carbocations, M2)
(Accept the use of carbonium ions as an
alternative to carbocation)

(b)

(i)

Secondary OR 2

(ii)

C H 3C H

C H
H

CH 3C H CH

M 3 s tru c tu re o f c a rb o c a tio n

O SO 2O H

:O S O 2 O H

M1 arrow from double bond to H of H O bond

M2 arrow from bond to oxygen atom to show H O bond breakage
M4 arrow from lone pair of electrons to carbon atom of carbocation
(Penalise M1 if arrow goes to H2SO4 or to
formal positive charge on H, but ignore partial
charges on sulphuric acid unless wrong)
+

(Credit M2 for H ion)

(For M4, accept negative charge anywhere on
the ion)
(iii)

Catalyst ONLY
(Ignore homogeneous, heterogeneous)
[9]

5.

(a)

(i)

the joining together of monomers / small molecules (1)

to form long chains / large molecules (1)

(ii)

nCH2 = CH2

(-CH2CH2-)n (1)

allow n CH2 CH2 not n C2H4

(b)

1,2-dibromoethane (1)

(c)

electrophilic addition (1)

H

H
C

H
Br
Br

H
H

B r

:B r

Br

B r

words or diagrams to show attack by p electrons on Br atom

and either +/ on Br2 or e shift on BrBr (1)

correct carbocation intermediate (allow triangular representation) (1)

attack by Br (onto +ve carbon) leading to correct product (1)

(d)

(i)

C 38.71/12 = 3.23 ;

H 9.68/1 = 9.68 ;

O 51.61/16 = 3.23 (1)

ratio C:H:O = 1:3:1 /empirical formula = CH3O (1)

empirical mass = 31 so molecular formula = 2 CH3O = C2H6O2
(1)
(ii)

reagent = NaOH / KOH (1)

conditions = aqueous solution (dependent on first mark) (1)

(iii)

CH2BrCH2Br + 2NaOH

CH2(OH)CH2OH + 2NaBr

product = CH2(OH)CH2OH (condone missing brackets) (1)

correctly balanced (1)
if C2H6O2 given, allow second mark only
for CH2 Br CH2 Br + 2H2O CH2(OH)CH2(OH) + 2HBr
allow 2 marks if reagent in (ii) is H2O or aqueous solution
[15]

2.9 ALKENES EXTRA QUESTIONS MS

1.

(a)

C2H6 C2H4 + H2

(b)

Addition
(ignore self or chain as a preface to addition )
(penalise additional)
[2]

2.

Electrophilic addition
M1: curly arrow from C=C bond towards/alongside the side of H atom on
H1OSO2OH
(penalise M1 if arrow to H2SO4 OR to formal charge on H of H1O bond)
(ignore partial charges on H and O of H2SO4, but penalise if these are
incorrect on the H atom being attacked)
(credit M1 and M2 if correct curly arrow to H+ provided the anion is
present)
M2: curly arrow from HO bond towards/alongside the side of the O atom
on
HOSO2OH
(credit the arrow even if there are partial or formal charges on H and O
but the structure of H2SO4 is correct)
M3: correct structure of the carbocation
(penalise use of sticks in this structure)
M4: curly arrow from lone pair on an individual oxygen atom of
(correct formula for) hydrogensulphate ion towards/alongside C atom
bearing the positive charge
(insist that the an ion has the correct formula with a lone pair of
electrons and a negative charge)
[5]

3.

Type of isomerism
Explanation

geometrical or
restricted rotation or
double bond rigid (1)
[2]

4.

H 3C

CH

H 3C

(1 )

C H

(1 )
3

H
accept

C H

C H

and

CH

C H

Credit 1 mark for a correct formula for but-2-ene

Credit 1 mark for any pair of cis / trans isomers

Geometric(al)
Or cis-trans
Or diastereoisomerism
NOT stereoisomerism
[3]

5.

(i)

+ H

or C6H10 + H2 C6H12
(ii)

Reagent(s)

Br2 or KMnO4 (1)

Observation(s)

no charge (1)
[3]

6.

(i)

Electron pair/ lone pair acceptor OR seeking/bonds

with an electron pair
(insist on reference to a pair of electrons)

(ii)

M1 curly arrow from middle of C=C bond of the alkene towards/

alongside the H atom of the H-Br;
(penalise arrows which go towards one of the
carbon atoms) (ignore a partial negative charge
on the C=C)
M2 curly arrow from H-Br bond to side of Br atom;
(penalise M2 if there are formal charges on HBr
or if there are partial charges which are the
wrong)
(penalise M2 if the single bond has two dots in
addition to the line)
M3 correct structure for carbocation;
(penalise M3 if the positive charge is placed on
the end of a bond) (penalise M3 if any alkene
other than ethene is used - all other marks can
score)
M4 curly arrow from lone pair on bromide ion to the positive
carbon
of carbocation, ensuring that bromide ion has a negative charge;
[5]

7.

(a)

Ml credit a correct structure for either geometrical isomer and its

designation as either cis or trans.

OR credit two correct geometrical isomer structures (ignore the names)
OR credit two correct names for cis pent-2-ene and trans pent-2-ene
(ignore the
structures)
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)
(b)

(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)
M2 curly arrow from H-Br bond to side of Br atom
M3 correct structure for correct secondary carbocation
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)

(ii)

1-bromopentane

(iii)

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

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)
[9]

8.

(1 ) M 4
a rro w
H 3C
(i)

H
(1 )
a rro w
M 1

C
H

H 3C

:B r
+

B r
(1 )

a rro w
M 2

CH

M 3
(1 ) c a rb o c a tio n

If wrong carbocation, lose structure mark

If wrong alkene, lose structure mark
Can still score i.e. penalise M3
Penalise M2 if
polarity included incorrectly
no bond between H and Br
bond is shown as
or

(ii)

C H 3C H 2C H

(1 )

credit secondary carbocation here if primary carbocation has

been used in (i)

Ignore attack on this carbocation by B r

[5]

9.

(a)

melting point increases (1)

boiling point increases(1)
or

they are liquids, the higher members are solids(1)

density increases(1)
viscosity increases(1)
(b)

addition (1)
polymerisation (1)

(c)

(i)

C2H4 + H2O C2H5OH - must show the functional group (1)

(ii)

vapour phase / high temperature (300 50C) (1)

high pressure 70cl 20 (1)
if high T and high p, then only 1 mark, value for either gives 2nd
mark
strong acidic catalyst /H3PO4 (1)

(iii)

electrophilic (1)
addition (1)
[10]

10.

(i)
Iso m e r 1
Cl

C l
C

Iso m e r 2

e ith e r o rd e r

Cl
(1 )

C l

Cl Cl
[c re d it

(1 )

C
C l

and

H ]

C l
(ii)

restricted rotation OR no rotation OR cannot rotate (1)

[3]

11.

(a)

e le c tr o p h ilic

a d d i t i o n (1)

(1 )

C H

+
H 2C

Cl
Cl

(1 )

(1 )

H 2C

Cl

CH
Cl

(1 )
2

(b)

C 2H 4C l2

CH

or

Cl

CH

Cl

H C l

Cl

(1)
(c)

ester or alkoxy alcohol (1)

(d)

(i)

HOCH2CH2OH (1)

(ii)

high electron density of double bond (1)

repels OH or nucleophile (1)

[10]

12.

(a)

geometrical or cis-trans isomers (1)

due to restricted rotation (1)

(b) (i)

C H B rC H 2 C H

(1 )

C H 2 C H B rC H

(1 )

(ii)

electrophilic addition (1)

(iii)

C6H5 C H CH2CH3 (1)

C6H5CH2 C H CH3 (1)

both secondary but one is more stable (1)

[8]

13.

(i)

the same general formula or CnH2n / the same functional

group / a C=C / a double bond / differ from their immediate
neighbour by CH2
allow all straight chain alkenes

(ii)

increases
not just pent-l-ene highest; allow ethene lowest, pent-l-ene
highest

(iii)

methylpropene / 2methylpropene not 2-methylprop-2-ene (1)

ignore wrong punctuation

C H

H
C
H

H
C

H
H

C
or

C H

C H

allow 1 mark for but-2-ene with its correct structure (1)

m in im u m s tru c tu r e is C H 2 = C C H
C H

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

[4]

14.

Catalyst (c) phosphoric acid or (c) sulphuric acid (1)

Not dilute
accept correct formula
Conditions

Temp = High or 200500C (1)

Temp = medium or moderate or 50-100C

Pressure = High or 520 Mpa or 50200 atoms

Pressure = High or 24 Mpa or 2040 atoms

If. wrong, no catalyst given, allow phosphoric acid conditions

Equation

CH2 = CH2 + H2O CH3 CH2 OH

allow C2H4

allow C2 H5OH

not CH2 CH2

[4]

15.

M1 X is 1,2-dibromoethane only
M2 electrophilic addition
(both words needed)
M3 the double bond is a centre of electron density
OR electron-rich
OR nucleophilic
OR a source of an electron pair
OR a pi cloud/bond of electrons
M4 a dipole or polarity is induced/created/formed in the Br-Br
bond/molecule award this mark only if the quality of language justifies the award.
[15]

16.

An appropriate alkene; CH3CH2CHCH2 or (CH3)2CCH2

1
Isomer 1
1
Isomer 2
1
Position isomerism
1
Mechanism
+

electrophilic attack and electron shift to Br (Unless H used)

carbocation
reaction with carbocation
[Allow mechanism marks for the alkene
CH3CHCHCH3]
[Allow one mark if mechanism for minor
product given]
[7]

17.

(a)

Reaction 1

H2O or steam (1)

(b)
H

M 1

C
(1 )

CH
H

Br

(1 )

C
+

(1 )

M 4
s tru c tu re

:B r

(1 ) M 2
M 3
Penalise M2 incorrect + /

Penalise on alkene (M1)

Penalise dots on bonds once
Penalise M4 (structure) for use of wrong alkene
Penalise M1 for use of Br2
[5]

18.

ethane
ethene

tetrahedral (or 3d shown in diagram) (1)

(trigonal) planar (1)

bond lengths: C C in ethane longest or

C = C in ethene shortest
in ethene : 2 pairs of e/greater electron

109( 12 )
120

(1)
(1)

}
} (1)
density
/ bond (1)
[6]

19.

(a)
(1 )
H

(1 )
(C H 3 )2 C

B r

C H C H 2C H

(C H 3 ) 2 C

C H 2 C H 2C H

(1 )

:B r

(C H 3) 2 C

(1)

C H 2C H 2C H

(1 )

Br

2bromo2methylpentane (1)
tertiary carbonium ion more stable than secondary (1)

(b)

geometrical or cistrans isomerisation (1)

hex3ene or hex2ene (1)
R

R
C

R
(1 )

C
H

(c is )

H
C

C
R

(tra n s )

(1 )

[11]

20.

(1 )
H

B r

(1 )

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

CH
3

C H 3C H 2C H
(1 )

:B r

(1 )
+
C
C H

CH

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

C
C H

electrophilic addn (1) tertiary (1) 2-bromo-2-methylpentane (1)

+
C
H
C H 3C H 2C H C H C H 3
3 C H 2 C H C H C H 3
or
(1 )
(1 )
CH 3
Br C H 3
secondary (1)

3-bromo-2-methylpentane (1)

tertiary more stable than secondary (1)

[13]

21.

(a)

A alkene (1)
B halogenoalkane / bromoalkane / alkyl halide / haloalkane (1)
C alcohol (ignore primary, secondary) (1)

(b)
(c)

(i)

addition ignore nucleophilic / electrophilic / free radical (1)

(ii)

substitution not replacement / displacement (1)

Sodium hydroxide / NaOH / KOH not just hydroxide (1)

(B to C)
(B to A)

aqueous not dilute (1)

alcoholic (1)

mark alternatives as (d)

ignore references to concentration and temperature

CH
3

(d)

(i)

CH3CH(CH3)Br + NaOH CH3CH=CH2 + NaBr + H2O (1)

(ii)

CH3CH(CH3)Br + NaOH CH3CH(CH3)OH + NaBr (1)

allow molecular formulae C3H7Br; C3H8O; C3H6

allow ionic versions (with OH , Br )

(e)

arrow from O of OH to C joined to Br (1)

lone pair not needed
CBr polarity shown by + or
heterolytic fission of CBr bond shown by arrow from bond between C
and Br to Br or
intermediate with partial bonds and minus sign (1)

Br as product (1)
allow all 3 marks if 1-bromopropane identified as B
[13]