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a. Label the four stereogenic centres in sorbitol as R or S.

b. How are sorbitol and A related?

c. How are sorbitol and B related?

Short Answer

Expert verified

a.

b. Diastereomers.

c. Enantiomers.

Step by step solution

01

Stereogenic centres

The stereogenic centers or chiral centers are directly related to the groups or substituents in the molecule. If the four different substituents are bonded with a common carbon atom, then the carbon atom is a stereogenic center.

02

Enantiomers  

The inverted stereochemistry is obtained in the enantiomers. The mirror images are non-superimposable in this case.

03

Diastereomers

The pairs which are not mirror images of each other are diastereomers. The stereochemistry of the diastereomers differs at only one carbon center.

04

Explanation

a. The sorbitol has three isomers. The three isomers are obtained by

changing the stereochemistry of the groups at the chiral center.

The R and S nomenclature are assigned according to the priority of the groups.

The order of the given groups is as:

OH>R>H

Therefore, the clockwise movement in the molecule gives R, and the anticlockwise movement gives S.

b. The sorbitol has R, R, R, S, and the A molecule has R, R, S, S. Therefore, it is a diastereomer.

c. The sorbitol has R, R, R, S, and the B molecule has S, S, S, R. Therefore, it is an enantiomer.

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Most popular questions from this chapter

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.

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b.

The amino acid (S)-alanine has the physical characteristics listed under the structure.

a. What is the melting point of (R)-alanine?

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d. What is the optical rotation of a racemic mixture of (R)- and (S)-alanine?

e. Label each of the following as optically active or inactive: a solution of pure (S)-alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine.

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?

A limited number of chiral compounds having no stereogenic centers exist. For example, although A is achiral, constitutional isomer B is chiral. Make models and explain this observation. Compounds containing two double bonds that share a single carbon atom are called allenes. Locate the allene in the antibiotic mycomycin and decide whether mycomycin is chiral or achiral.

±á°ä≡C-°ä≡C-°ä±á=°ä=°ä±á-°ä±á=°ä±á-°ä±á=°ä±á-°ä±á2CO2H

How are the compounds in each pair related to each other? Are they identical, enantiomers, diastereomers, constitutional isomers, or not isomers of each other?

a.

and

b.

and

c.

and

d.

and

e.

and

f.

and

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