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Chapter 5: Q.20 (page 194)

Which compounds are meso compounds?
a.
b.
c.

Short Answer

Expert verified

a. Meso compound.

b. Not a meso compound.

c. Meso compound.

Step by step solution

01

Meso compounds

The compounds with atleast two stereogenic centers and a plane of symmetry are termed meso compounds.

The meso compounds are achiral.

02

Plane of symmetry

There are two planes of symmetry as follows:

The horizontal plane of symmetry bisects the horizontal plane into two equal halves.
The vertical plane of symmetry bisects the vertical plane into two equal halves.

03

Explanation

a. The given compound has two stereogenic centers (as two centers have four different groups), and it has the same substituents with the same stereochemistry.

Therefore, a vertical plane of symmetry exists in this compound. Hence, the compound is a meso compound.

Meso compound with a vertical plane of symmetry

b. The given compound has 2 stereogenic centers (as two centers have four different groups), but it does not have the substituents with the same stereochemistry.

Therefore, a plane of symmetry does not exist in this compound. Hence, the compound is not a meso compound.

Not a meso compound

c. The given compound also has 2 stereogenic centers, and it has the same substituents with the same stereochemistry.

Therefore, a vertical plane of symmetry exits in this compound. Hence, the compound is a meso compound.

Meso compound with a vertical plane of symmetry

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Most popular questions from this chapter

Locate the stereogenic centers in each compound.

a.

b.

Locate the stereogenic centers in each drug.

a.

b.

c.

Drawn are four isomeric dimethylcyclopropanes.

a. How are the compounds in each pair related (enantiomers, diastereomers, constitutional isomers): A and B; A and C; B and C; C and D?

b. Label each compound as chiral or achiral.

c. Which compounds, alone, would be optically active?

d. Which compounds have a plane of symmetry?

e. How do the boiling points of the compounds in each pair compare: A and B; B and C; C and D?

f. Which of the compounds are meso compounds?

g. Would an equal mixture of compounds C and D be optically active? What about an equal mixture of B and C?

A molecule is achiral if it has a plane of symmetry in any conformation. Each of the following conformations does not have a plane of symmetry, but rotation around a carbon–carbon bond forms a conformation that does have a plane of symmetry. Draw this conformation for each molecule.

a.

b.

Rank the following groups in order of decreasing priority.

${-F,-NH}_{2} {,-CH}_{3},-OH$
${-CH}_{3,} {-CH}_{2} {CH}_{3} {,-CH}_{2} {CH}_{2} {CH}_{3} {,-(CH}_{2})_{3} {CH}_{3}$
${-NH}_{2} {,-CH}_{2} {NH}_{2} {,-CH}_{3} {,-CH}_{2} {NHCH}_{3}$
${-COOH,-CH}_{2} OH,-H,-CHO$
${-Cl,-CH}_{3},-SH,-OH$
${-C≡CH,-CH(CH}_{3})_{2} {,-CH}_{2} {CH}_{3} {,-CH=CH}_{2}$

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