12.

3 extra questions ms
1.

(b)

melting point increases (1)

boiling point increases(1)
or

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

density increases(1)
viscosity increases(1)
(c)
(d)

max 2

addition (1)
polymerisation (1)

(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)

2
[10]

2.

(a)

( C H

C H

(1 )

C H 2C H

H
C

(b)

(i)

120

(1 )
C H 2

(1 )

C H

C H

CH

(1 )

(ii)
B r

B r

B r

Br

1,2,3,4 (1) - tetra bromobutone (1)

electophilic addition (1)
[7]

2 C H 2= C H
3.

+ O

2 C H

(a)

C H

(1 )

(1 )

strained ring or bond repulsion (1)

bonds break easily or ring opens easily (1)
(b)

(i)

C H

CH

H 2O

H O C H 2C H 2O H

(1 )

O
antifreeze or polyester (1)
(ii)

HOCH2CH2NH2 (1)

3
[7]

4.

To produce polymers (1)

Mill Hill High School

1
1

[1]

5.

+ H

(i)

or C6H10 + H2 C6H12
(ii)

Reagent(s)

Br2 or KMnO4 (1)

Observation(s)

no change (1)
[3]

6.

(a)

(i)
(ii)

the joining together of monomers / small molecules

(1)

to form long chains / large molecules

(1)

nCH2 = CH2

(-CH2CH2-)n

(1)

allow n CH2 CH2 not n C2H4

(b)

1,2-dibromoethane

(1)

(c)

electrophilic addition

(1)

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)

4
[8]

7.

(a)

Reagent
Catalyst

oxygen or O2 (1)
silver or Ag (1)

CH
(b)

Structure

(1 )

Explanation

(c)

C H

strained ring or bond repulsion or 60 bond angles (1)

ring opens easily or weak bonds (1)
not unstable

addition (1)
Not additional

1
H
(d)

C
H

C H

C H

(1 )

C
C H

May circle 4 Cs separately

1
[7]

Mill Hill High School

8.

(a)

(i)

H2C=CH2 + O2

O
H 2C

CH

Product (1) M1
Correct balanced equation (1) M2

(OR 2)
2

OR C2H4
OR CH2=CH2
OR CH2CH2
O2 NOT [O]
For M2, allow credit when C2H4O OR CH2CH2O are used

(ii)

strained (ring) (1)

NOT weakened
NOT unstable

(iii)

Structure:

CH

C H

O H

O H

(1)

Use: antifreeze (1)

or production of Terylene
or feedstock for polyester or PET
NOT plasticiser
NOT solvent
NOT de-icer
NOT alcohol

H 3C

CH

H 3C

(1 )

H
C H

(1 )
3

(b)

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
[8]

9.

(a)

(i)

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

C
H

H
H 3C

:B r
+

B r
(1 )

CH

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

a rro w
M 2

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
Mill Hill High School

bond is shown as
+

(ii)

C H 3C H 2C H

or

(1 )

credit secondary carbocation here if primary carbocation has been used in (i)

Ignore attack on this carbocation by B r

5
[5]

10.

(a)

(a c id )
K M nO

Test

B r2

Result

d e c o lo u riz e d
(b ro m id e
C E = 0)

(1 )

c o lo u rle s s o r b ro w n (1 )

H O
(b)

H O O C

p e n a liz e

C O O H
C

or

[1 ]

C
CO O H
C

cannot rotate double bond (1)

2 different groups on each C (1)

H O O C
(c)

CH

C H

(1 )

CO O H
H

H O O C

CH

(1 ) ..
Br

(1 )

(1 )
C H

C O O H

B r
penalize first mark : if wrong acid (unless if same error as in (b)) or if Br 2

4
[9]

11.

(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)

6
[8]

12.

(a)

CH2=CH2 + O2 (1) or air

Mill Hill High School

Ag catalyst [1] C H 2
250 300C [1]
O

C H

(1)
4

explosive or flammable (1) toxic (1)

(b)

max 5

strained ring or 60 angles or bond repulsion

ring opens easily or weak bonds
CH 2 C H 2
+ H2O HOCH2CH2OH
O
antifreeze or polyester

(1)
(1)
(1)
(1)
[9]

13.

(a)

ethane
ethene

109( 12 )
120

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

(1)
(1)

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

(b)
(1 )
H

(1 )
(C H 3 )2 C

B r

C H C H 2C H

(C H 3 ) 2 C

(1 )

C H 2 C H 2C H
: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)

(c)
Polymerisation:
Short-chain(ed molecule)s / monomers join / combine to make long-chiain(ed molecule)s
OR
small molecules join / combine to make long / long-chained / big molecules (1) (QoL)
Equation: nH2C=CH2 -(-CH2-CH2-)-n (1)
Equation must show n correctly and be balanced with clear structure for polymer showing the
bonds between each CH2 and extending through the brackets.
Credit nC2H4 or nCH2=CH2 in the equation
4
[17]

(1 )
14.

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

CH

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

Mill Hill High School

(1)
5

[13]

15.

geometrical or cistrans isomerisation (1)

hex3ene or hex2ene (1)
R

R
C

(1 )

(c is )

C
(tra n s )

(1 )

4
[4]

16.

(a)

Molecules with same structural formula (1)

but atoms arranged differently in space (1)

Geometrical or cistrans (1)

C = C or double bond (1)
2 different groups on each C (1)
no rotation of C = C (1)

Max 3

(b)

C H

C H

C H

(1 )

CH

C H

+
C H

C H

Br

B r:

(1)

CH

(1 )

(1 )

b u t - 2 - e n e : g e o m e tric a l (1 )
C H

CH

and

p ro d u c t:

(1 )

C
H

C
CH

H
CH

o p tic a l (1 )

CH

C*
Br

C H 2C H

(1 )
[13]

17.

Oxygen or air (1) Can score from the equation

Silver catalyst (1)
Linked to process: e.g. Consequence of leaks etc. (1)
Hazard 1 = flammable or explosive (1)
Hazard 2: = toxic or causes respiratory failure or neurological effects (1)
(CH2CH2)O +H2O HOCH2CH2OH (1) Not (CH2CH2)2O, CH2CH2O, C2H4O, but only
penalise once
Uses include antifreeze or polyester formation / terylene (1), Not plastics, polymers,
surfactants
[7]

Mill Hill High School

18.

(a)

2C H 2= C H

+ O

2C H

CH

(1 )

(1 )

O
Ag catalyst (1) 250 300C (1)

(b)
CH

CH

H 2O

H O C H 2C H 2O H

CH

C H 3O H

(1 )

O
CH

H O C H 2C H 2O H

(1 )

19.

(i)

[5]

Electrophilic addition (1)

B r

B r

(1 )

B r

(1 )

(1 )

(1 )

B r
B r

:B r

1 ,2 - d ib r o m o c y c lo h e x e n e
(1 )

(ii)
CH

C H

(1 )
1
[7]

20.

oxygen

(1)
O

H 2C

CH

+ O

Ag catalyst
250 C
product toxic
product flammable
danger of explosion

H 2C

CH

(1)
2

(1)
(1)
(1)
(1)
(1)
[7]

21.

No mark scheme available

Mill Hill High School