1.

B
[1]

2. D
[1]

3. C
[1]

4. C
[1]

5. B
[1]

6. (a)
C l H C l C H C lC H 3

C C C C
H C H C lC H 3 H H
one correct structural formula;
two distinct isomeric structures shown;
CH CH 3
3

C C
H H CH CH Cl
C lH C H C
Cl Cl
one correct structural formula shown as 3-D;
two distinct isomeric structures shown; 4

(b) it contains equal amounts/moles of the two optical isomers/enantiomers/

d (dextro/dextrorotatory) and l(levo/levorotatory); 1

(c) polarimeter/plane-polarized light;

plane (of polarization) rotated in opposite directions;
no rotation for racemic mixture; 3

1
 (d)
H H H Cl

H H H H
H Cl H H

Cl H Cl H
one correct structural formula;
two distinct isomeric structures shown; 2
[10]

7. (a) restricted rotation because CC bond is now part of a cyclic system; 3
H H H H

H H ; H Cl ;
H H H H

Cl Cl Cl H

Award [1] for each correct 3D structure.

If correct structure, but not 3D, or wrongly labelled award [1]
only.
Accept 1,3-disubstituted cyclo compound, or any other correct
isomer.

(b) (i) 2
HOOC COOH H COOH
C C ; C C ;
H H HOOC H
(ii) cis isomer (has lower melting point than the trans-isomer);
intramolecular hydrogen bonds/weaker intermolecular forces
/less close packing; 2
(iii) (gentle) heating of a sample of each isomer;
cis isomer readily releases water vapour (forming a cyclic anhydride); 2

2
 (c) (i) 2-chloropentane;
C 3H 7 C 3H 7

C ; C ;

H C1 C1 H
CH3 CH3
3
Award [1] for each correct 3D structure.
If correct structures, but not 3D, award [1] only.
(ii) rotation of the plane polarized light in opposite directions; 1
[13]

8. (i) optical isomers rotate the plane of polarized light

(in opposite directions); 1
(ii) 1
H H O
N C* C
C H 3 ;
The chiral centre may be indicated by an asterisk, circle,
highlight, etc.

(iii)

H
H
C
CO C
NH CO
CH 3 CH 3 NH

Award [1] for one 3-D structure and [1] for showing that the second
structure is a mirror image of the first one. 2
[4]

9. (a) restricted/no rotation around double bond/pi bond; 1

3
(b) Accept either of these structures
Cl H H Cl

C C C C ;

Cl CH 3 H C H 2C l
two identical atoms on one side of double bond/interchanging CH3
and H/Cl and CH2Cl makes no difference; 2

(c)
H H

C C cis;
Cl C H 2C l

H CH 2Cl

C C tran s;
Cl H

Award [0] if structure of another isomer drawn.

Award [1] if both structures correct but unlabelled or wrongly
labelled.
Award [1] for each correctly drawn and labelled structure.
2

4
(d)
Cl Cl

C C
H ;

H C H

Cl H

C C
H ;

H C Cl

H
2
Award [0] if structure of another isomer drawn.
[7]

5
10. (a) (i) no rotation possible due to double bond/ bond; 1
Accept restricted or hindered rotation.
(ii) 2
H H

C ;
C

CH 3 C H 2C l
C is

CH 3 H

C C ;

C H 2C l
H
tran s

OR
H
H

C C ;

Cl C H 2C H 3
C is

H
Cl
;
C C

H C H 2C H 3
tran s

OR
CH3 CH 3

C C

C is H Cl

H CH 3

C C

tran s CH 3 Cl

6
 (iii)
H H

C H
C
;
H *C C H 3

C l
2
Award [1] for the structure and [1] for showing * on the correct
carbon atom.

(b) restricted rotation because CC bond is now part of a cyclic system; 3
CH 2
Cl H

C C ;

H Cl
tran s

CH 2
H H

C C ;

Cl Cl
C is
[8]

11. CH3CH(OH)CH2CH3;
Accept more detailed formula.
butan-2-ol;
Accept 2-butanol.
ECF for correct name of another C4 alcohol.

contains a chiral/asymmetric carbon atom/four different groups around one

carbon atom;
(plane of) plane-polarized light rotated in opposite directions; 4
[4]

12. C
[1]