A Level Chemistry

Optical isomers

Optical isomers exam questions

1.

must attempt 3D
use
symbol in the tools to denote whether or not each chiral C
is a reflection of the one given in the question

each chiral C must have 2 bonds, 1 wedge bond (IGNORE shading) & 1
dash bond (IGNORE wedge)
check the clockwise orientation of each C. For each C start with the H and if
on the:

top C the H is followed by COOH it is not a mirror image.

If it is a mirror image annotate using RE.

bottom C the H is followed by CH3 it is not a mirror

image. If it is a mirror image annotate using RE.
the four groups can be attached in any order. If the molecule is drawn upside
down clockwise becomes anti-clockwise.
MUST check that the drawn structure is non-superimposable irrespective of
the orientation or the way it has been drawn.
IGNORE bond linkage for all groups
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A Level Chemistry

2.

Optical isomers

(a)

(i)
H2NCHRCOOH /
(1)
allow R CH NH2 and COOH in any order

(ii)

they both have the

group / or in words (1)
NOT just they both have NH2 and COOH
R group is H in glycine and CH2CH2COOH in glutamic acid (1)

(b)
NH3+ (1)

one COO (1)

-COOH and
side chain
unaffected
(1)

both COO (1)

H2N- and rest of
molecule (1)

(c)

glutamic acid/molecule with optical isomers

is chiral (1)
has four different / distinguishable groups attached to a carbon (1)
NOT just different atoms
the mirror images/isomers cannot be superimposed AW (1)
one diagram showing two 3-D bonds not opposite each other,
and not with angles looking like 90

(1)

3-D diagram of the other isomer (allow ecf on one 3-D error) (1)
all groups correctly connected for glutamic acid in both diagrams (1)
glycine
only has three different groups / two groups are the same /
3-D diagram used to show symmetry (1)

quality of written communication

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A Level Chemistry

Optical isomers

for correct use and organisation of at least one technical term:

*(in the correct place), non-superimposable, enantiomer, stereoisomer(ism),
tetrahedral, assymetric (1)
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A Level Chemistry

3.

Optical isomers

(b)

(i)

(1)
(ii)

optical (isomerism) (1)

(iii)

(stereo)isomers are non-superimposable (mirror images) /

the molecule is asymmetric /
the carbon has four different groups attached (1)

(1)

one 3-D isomer with all groups correct (1)

second isomer is a mirror image of a reasonable attempt at 3-D (1)
for the 3-D bonds allow:

but NOT:

(c)

(d)

Any three of:

only one stereoisomer has the right 3-D shape /

shape similar to noradrenaline /
is (pharmacologically) active ora

presence of other (inactive) stereoisomers:

will increase the amount needed for the dose

may give harmful side effects

may increase cost of separation

ANY 3 out of 4 marks (1)(1)(1)

use naturally occurring / enantiomerically pure amino acids

OR
use a stereospecific catalyst / enzyme / micro-organisms
OR
separate the mixture using a suitable method (1)

1
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A Level Chemistry

Optical isomers

A Level Chemistry

4.

Optical isomers

(i)
(ii)

C13H20O3 (1)

ketone (1)
ester (1)
alkene (1)

both optical (1)

E/Z (1)

(iii)

(iv)

possible side effects of other chiral compound (1)

increased costs/difficulty of separating of isomers (1)
using bacteria within synthetic route (1)

2 max
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5.

(i)
(1)
(ii)

structure with correct use of at least two 3-D bonds (1) e.g.

1
allow ecf if lactic acid is labelled in (i)
NOT if all four bond angles at 90
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A Level Chemistry

6.

(i)
four different groups attached (1)

Optical isomers

a carbon with

a chiral carbon /centre (1)

different spatial / 3-D arrangement (of the groups) (1)
(stereo)isomers / mirror images are non-superimposable / molecules
are asymmetric (1)
ANY 3 out of 4 marks
(ii)

(iii)

(iv)

contains 2 chiral centres (1)

each can have 2 (stereo)isomers/ 22 possibilities AW (1)

use naturally occurring / enantiomerically pure amino acids

OR
use a stereospecific catalyst / enzyme / micro-organisms
OR
separate the mixture using a suitable method (1)

higher doses are required (1)

the drug /other stereoisomers may have (harmful) side-effects (1)

2
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Optical isomers

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8.

Optical isomers

stereoisomers have same structural formula but a

different arrangement in space 1

2
Diagrams of cis and trans isomers

Diagrams showing two optical isomers2

(If diagrams are wrong / not used give 1 mark for mention
of cis/trans and optical isomerism)
H2O at 90/ adjacent in cis / 180 / opposite in trans (not from diagram)
Optical isomers are non-superimposable mirror images
1

Quality of Written Communication:

At least three of the following key words used in context:
non-superimposable, mirror images, optical, cis/trans, geometric,
plane polarised, rotate, chiral, asymmetric
1
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9.

(a) (i)
1 mark for correct 3-D diagram of cis isomer
1 mark for correct 3-D diagram of trans isomer
1

(Allow planar diagrams if two appropriate 90 angles are shown)

Allow any suitable 3-D diagrams. Possibilities to include:

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A Level Chemistry

(ii)
(b)

Optical isomers

Geometric / cis trans

Optical isomerism

1
1

1 mark for using cis isomer

1
1 mark for correct 3-D diagrams which are mirror images of each other.

(If all diagrams are drawn as non-3d do not penalise in (b))

Allow any suitable 3-D diagrams such as:

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10.

(ii)

(i)
drawn
trans isomer drawn
(ignore any charges)

cis isomer
1
1

cis / trans or geometric

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