Theoretical Multiple Choice Questions on Optical Isomerism
Based on NCERT Texts
Q1. Which of the following best defines an optically active compound?
(A) A compound that is insoluble in water.
(B) A compound that boils at a very high temperature.
(C) A compound that rotates the plane of plane polarised light
when passed through its solutions.
(D) A compound that forms a stable crystal lattice.
Answer: C
Explanation: Optically active compounds are those that rotate the
plane of plane polarised light when it is passed through their
solutions.
Q2. A compound is described as laevorotatory if it:
(A) Rotates the plane polarised light to the right (clockwise
direction).
(B) Is optically inactive and does not rotate plane polarised
light.
(C) Rotates the plane polarised light towards the left
(anticlockwise direction).
(D) Has a mirror image that is superimposable on itself.
Answer: C
Explanation: If the light is rotated towards left (anticlockwise
direction), the compound is said to be laevo-rotatory or the l-form,
and a negative ( ) sign is placed before the degree of rotation.
Q3. What is an asymmetric carbon atom or stereocentre, according to J.
Van't Hoff and C. Le Bel?
(A) A carbon atom bonded to two identical groups and two
different groups.
(B) A carbon atom that forms a double bond within a molecule.
(C) A carbon atom where all four substituents attached are
different, and its mirror image is not superimposable.
(D) A carbon atom that is sp2 hybridised, allowing for planar
geometry.
Answer: C
Explanation: If all the substituents attached to that carbon are
different, the mirror image of the molecule is not superimposed on the
molecule; such a carbon is called asymmetric carbon or stereocentre.
Q4. Which characteristic defines a chiral object?
(A) It possesses a plane of symmetry.
(B) It is identical to its mirror image.
(C) Its mirror image is superimposable on the object.
(D) It is non-superimposable on its mirror image.
Answer: D
Explanation: The objects which are non-superimposable on their mirror
image (like a pair of hands) are said to be chiral, and this property
is known as chirality.
Q5. Propan-2-ol is an achiral molecule because:
(A) It is optically active.
(B) It contains an asymmetric carbon atom.
(C) It does not contain an asymmetric carbon and its mirror image
is superimposable on the molecule.
(D) It is a cyclic compound.
Answer: C
Explanation: Propan-2-ol does not contain an asymmetric carbon, as all
the four groups attached to the tetrahedral carbon are not different.
Its mirror image can be completely overlapped with the structure,
making it an achiral molecule.
Q6. What is the relationship between two compounds that are
enantiomers?
(A) They are identical compounds with the same physical and
chemical properties.
(B) They are stereoisomers that are non-superimposable mirror
images of each other.
(C) They are structural isomers with different functional groups.
(D) They are different compounds that rotate plane polarised
light in the same direction.
Answer: B
Explanation: The stereoisomers related to each other as non-
superimposable mirror images are called enantiomers.
Q7. A racemic mixture is formed when:
(A) An optically active compound undergoes inversion of
configuration.
(B) Two enantiomers are present in equal proportions, resulting
in zero optical rotation.
(C) A compound with multiple asymmetric centres is optically
active.
(D) A pure enantiomer is converted into a different compound.
Answer: B
Explanation: A mixture containing two enantiomers in equal proportions
will have zero optical rotation, as the rotation due to one isomer
will be cancelled by the rotation due to the other isomer. Such a
mixture is known as racemic mixture or racemic modification.
Q8. Which amino acid is an exception to the rule that naturally
occurring alpha-amino acids are optically active?
(A) Alanine
(B) Valine
(C) Glycine
(D) Serine
Answer: C
Explanation: Except glycine, all other naturally occurring -amino
acids are optically active, since the -carbon atom is asymmetric.
Q9. In the context of carbohydrates, what do the letters 'D' and 'L'
primarily represent?
(A) The specific direction of optical rotation (dextro- or
laevorotatory).
(B) The relative configuration of a stereoisomer with respect to
glyceraldehyde.
(C) The number of hydroxyl groups in the molecule.
(D) The overall size and complexity of the carbohydrate
structure.
Answer: B
Explanation: The letters 'D' or 'L' before the name of any compound
indicate the relative configuration of a particular stereoisomer of a
compound with respect to configuration of some other compound,
configuration of which is known. In the case of carbohydrates, this
refers to their relation with a particular isomer of glyceraldehyde.
Q10. Which statement correctly describes the relationship between D/L
notation and optical activity?
(A) All D-series compounds are dextrorotatory, and all L-series
compounds are laevorotatory.
(B) The D-configuration of a compound always correlates with a
positive (+) optical rotation.
(C) The letters 'D' and 'L' have no relation with the optical
activity of the compound.
(D) A compound with D-configuration will always have a higher
optical rotation magnitude than its L-isomer.
Answer: C
Explanation: It should be remembered that 'D' and 'L' have no relation
with the optical activity of the compound. For example, D-( )-fructose
is a laevorotatory compound.
Q11. What is the stereochemical outcome for optically active alkyl
halides undergoing an SN2 mechanism?
(A) Inversion of configuration.
(B) Racemisation.
(C) Retention of configuration.
(D) Elimination to form an alkene.
Answer: A
Explanation: In case of optically active alkyl halides, the product
formed as a result of SN2 mechanism has the inverted configuration as
compared to the reactant. This is because the nucleophile attaches
itself on the side opposite to the one where the halogen atom is
present.
Q12. The stereochemical consequence of SN1 reactions involving
optically active alkyl halides is:
(A) Complete inversion of configuration.
(B) Racemisation.
(C) Predominant retention of configuration.
(D) Formation of a single optically active product.
Answer: B
Explanation: In case of optically active alkyl halides, SN1 reactions
are accompanied by racemisation. This is because the carbocation
formed in the slow step being sp2 hybridised is planar (achiral) and
the nucleophile can attack from either side.
Q13. When assigning the configuration of monosaccharides as D- or L-,
which specific carbon atom is used for comparison with glyceraldehyde?
(A) The carbon atom of the carbonyl group.
(B) The highest numbered asymmetric carbon atom.
(C) The lowest asymmetric carbon atom.
(D) Any carbon atom with a hydroxyl group.
Answer: C
Explanation: For assigning the configuration of monosaccharides, it is
the lowest asymmetric carbon atom which is compared.
Q14. The term 'retention of configuration' means that during a
chemical reaction:
(A) The compound converts into its mirror image.
(B) A new asymmetric centre is formed.
(C) The spatial arrangement of bonds to an asymmetric centre is
preserved, and no bond to the stereocentre is broken.
(D) The direction of optical rotation necessarily remains the
same.
Answer: C
Explanation: Retention of configuration is the preservation of the
spatial arrangement of bonds to an asymmetric centre during a chemical
reaction or transformation. In general, if during a reaction, no bond
to the stereocentre is broken, the product will have the same general
configuration of groups around the stereocentre as that of reactant.
Q15. Which of the following best describes the structural requirement
for a molecule to exhibit optical isomerism?
(A) It must contain a carbon-carbon double bond.
(B) It must be a cyclic compound.
(C) It must possess a carbon atom with four different
substituents (an asymmetric carbon) and be non-superimposable on
its mirror image.
(D) It must have a linear structure.
Answer: C
Explanation: The asymmetry of the molecule along with non
superimposability of mirror images is responsible for the optical
activity in such organic compounds. This typically occurs when a
central carbon is attached to four different substituents.
