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Chapter 5: Q.17 (page 192)

Label the two stereogenic centers in each compound and draw all possible stereoisomers.

a.

b.

Short Answer

Expert verified

a.

stereogenic centers

b.

Step by step solution

01

Stereogenic center

The four different groups are bonded with a common carbon. The carbon point is known as stereogenic center.

02

Stereoisomers

The stereoisomers are the enantiomers or diastereomers. The enantiomers are non-superimposable mirror images, and the diastereomers are not part of mirror images.

The formula to calculate stereoisomers from stereogenic centers is:2n.

Where n is the stereogenic center number.

03

Explanation

a. The stereogenic centers in the given compound are 2 as shown below:

stereogenic centers

Therefore, the possible stereoisomers are 4, which are the non-superimposable mirror images as shown:

Stereoisomers

Stereoisomers

b. The stereogenic centers in the given compound are shown as:

Stereogenic centers

The possible stereoisomers are the non-superimposable mirror images as shown:

Stereoisomers

Stereoisomers

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Most popular questions from this chapter

Draw the structure of (S)-citalopram, a drug used to treat depression and anxiety that is much more potent than its R enantiomer.

citalopram

Draw all possible constitutional and stereoisomers for a compound of molecular formulaC6H12 having a cyclobutane ring and two methyl groups as substituents. Label each compound as chiral or achiral.

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

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

b. How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine?

c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine?

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.

A natural product was isolated in the laboratory, and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of water. What is the specific rotation of this compound?

Draw the structures for each compound.

  1. (R)-3-methylhexane
  2. (4R,5S)-4,5-diethyloctane
  3. (3R,5S,6R)-5-ethyl-3,6-dimethylnonane
  4. (3S,6S)-6-isopropyl-3-methyldecane
See all solutions

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