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Locate the stereogenic center in each compound and draw both enantiomers.

a.

b.

c.

Short Answer

Expert verified

The stereogenic centers in the given compounds and their enantiomers are represented below.

a.

b.

c.

Step by step solution

01

Stereogenic centers

The points in a molecule that could generate stereoisomers on interchanging two of the substituents attached to it are named stereogenic centers.

02

Enantiomers

The molecules whose mirror images are non-superimposable are termed enantiomers.

03

Stereogenic centers in the given molecules

The carbon atoms that are hybridized and are bonded to four other groups/atoms are stereogenic centers.

a. The given molecule consists of only one stereogenic center.

Stereogenic center in a

b. The given molecule consists of one stereogenic center.

Stereogenic center in b

c. The molecule consists of one stereogenic center.

Stereogenic center in c

04

Enantiomers of the given compounds

The enantiomers of the given compounds are provided below.

a.

Enantiomers of compound a

b.

Enantiomers of compound b

c.

Enantiomers of compound c

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Most popular questions from this chapter

A sulfonium ion (R3S+) is a stereogenic center if three different alkyl groups are bonded to sulfur because sulfur is surrounded by four different groups, including its lone pair. In assigning an R or S designation to sulfur, the lone pair is always assigned the lowest priority (4). SAM, S-adenosylmethionine, is a biologically active sulfonium ion that we will learn about in Section 7.16. Locate all the stereogenic centers in SAM, and assign an R,S designation to each center.

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?

Classify each pair of compounds as constitutional isomers or stereoisomers.

Compare the physical properties of the three stereoisomers of 1,3-dimethylcyclopenatane.

  1. How do the boiling points of A and B compare? What about A and C?
  2. Characterize a solution of each of the following as optically active or optically inactive: pure A; pure B; pure C; an equal mixture of A and B; an equal mixture of A and C.
  3. A reaction forms a 1:1:1 mixture of A, B, and C. If this mixture is distilled, how many fractions would be obtained? Which fractions would be optically active and which would be optically inactive?

Explain each statement by referring to compounds A-E.

a. A has a mirror image but no enantiomer.

b. B has an enantiomer and no diastereomer.

c. C has both an enantiomer and a diastereomer.

d. D has a diastereomer but no enantiomer.

e. E has a diastereomer but no enantiomer.

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