Question 1

Which of the following statements best describes a chiral molecule?

Accepted Answer

A molecule that is not superposable on its mirror image.

Question 2

Which of the following molecules would be expected to be achiral?

Accepted Answer

A molecule with a plane of symmetry.

Question 3

How many stereoisomers are possible for a molecule with three chiral centers?

Accepted Answer

$$2^3 = 8$

Question 4

Which of the following best describes enantiomers?

Accepted Answer

Stereoisomers that are nonsuperposable mirror images of each other.

Question 5

A molecule with two chiral centers is found to be achiral. What is the most likely explanation?

Accepted Answer

The molecule is a meso compound.

Question 6

Which of the following is true about the R, S system for naming chiral centers?

Accepted Answer

R means the order of priority is clockwise.

Question 7

Which of the following is NOT a criterion for assigning priority in the Cahn-Ingold-Prelog system?

Accepted Answer

The boiling point of the substituents.

Question 8

Which of the following statements about meso compounds is correct?

Accepted Answer

Meso compounds have two or more chiral centers and are achiral due to a plane of symmetry.

Question 9

Which of the following best describes diastereomers?

Accepted Answer

Stereoisomers that are not mirror images of each other.

Question 10

Which of the following molecules can exist as a pair of enantiomers?

Accepted Answer

trans-1,2-cyclopentanediol

Question 11

Which of the following is a correct statement about the physical properties of enantiomers?

Accepted Answer

Enantiomers have identical physical and chemical properties in an achiral environment.

Question 12

Which of the following is an example of a configurational isomer?

Accepted Answer

cis-2-butene and trans-2-butene

Question 13

A molecule with the formula $$C_4H_{10}O$$ has two chiral centers. How many stereoisomers are possible?

Accepted Answer

$$2^2 = 4$

Question 14

Which of the following best describes atropisomers?

Accepted Answer

Enantiomers that differ due to hindered rotation and lack a chiral center.

Question 15

Which of the following statements about Fischer projections is correct?

Accepted Answer

Groups on the right and left are in front of the plane of the paper.

Question 16

Which of the following molecules is achiral due to the presence of a plane of symmetry?

Accepted Answer

cis-1,2-cyclohexanediol

Question 17

Which of the following is true about the relationship between (2R,3R)-erythrose and (2S,3S)-erythrose?

Accepted Answer

They are enantiomers.

Question 18

Which of the following is a correct application of the Cahn-Ingold-Prelog priority rules?

Accepted Answer

A -CH2Cl group has higher priority than a -CH2CH2CH3 group.

Question 19

Which of the following statements about conformational isomers is correct?

Accepted Answer

They can be separated at room temperature if the barrier to rotation is high.

Question 20

Which of the following best describes the relationship between cis- and trans-1,4-dimethylcyclohexane?

Accepted Answer

They are diastereomers.

Stereoisomerism and Chirality: Structure, Classification, and Nomenclature

Study Guide - Practice Questions