5. Chirality

For each compound, determine whether the molecule has an internal mirror plane of symmetry. If it does, draw the mirror plane on a three-dimensional drawing of the molecule. If the molecule does not have an internal mirror plane, determine whether the structure is chiral.

(d) 1,2-dichloropropane

(e)

For each compound, determine whether the molecule has an internal mirror plane of symmetry. If it does, draw the mirror plane on a three-dimensional drawing of the molecule. If the molecule does not have an internal mirror plane, determine whether the structure is chiral.

(a) methane

(b) cis-1,2-dibromocyclobutane

(c) trans-1,2-dibromocyclobutane

Which of the following compounds are meso?

(a)

How many stereoisomers are possible for each of the following molecules?

(a)

Which of the following compounds has a stereoisomer that is a meso compound?

e. 1,4-dichlorocyclohexane

f. 1,2-dichlorocyclobutane

A molecule of the type shown is discussed in greater detail in Section 6.5.1. Although it contains at least one atom with four different groups attached, why is it not a chiral molecule?

Which of the following compounds are meso?

(c)

Which of the following has an achiral stereoisomer?

e. 1,3-dibromocyclobutane

f. 2,4-dibromopentane

Which of the following has an achiral stereoisomer?

i. 1,2-dimethylcyclopentane

j, 1,2-dimethylcyclobutane