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Chapter 5: Q.16 (page 190)

What is the maximum number of stereoisomers possible for a compound with:

a. three stereogenic centers;

b. eight stereogenic centers?

Short Answer

Expert verified
  1. 8 isomers.
  2. 256 isomers.


Step by step solution

01

Stereogenic centre

The different groups at the chiral centers generate stereogenic centers.

02

Calculation of stereoisomers

The stereogenic centers give the number of stereoisomers.The formula used to calculate stereoisomer is shown as: 2n

Where n is the number of stereogenic centers.

03

Explanation

a. The number of stereoisomers is calculated as:

23=8

Where 3 is the given number of stereogenic centers.

b. The number of stereoisomers is calculated as:

28=256

Where 8 is the given number of stereogenic centers.

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Most popular questions from this chapter

Which of the following cyclic molecules are meso compounds?

a.

b.

c.

Draw the structures of (S,S)-ethambutol, a drug used to treat tuberculosis that is 10 times more potant than any of its other isomers.

ethambutol

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

Artemisinin and mefloquine are widely used antimalarial drugs. A ball-and-stick model of artemisinin appears on the cover of this text.

  1. Locate the stereogenic centers in both drugs.
  2. Label each stereogenic center in mefloquine as R or S.
  3. What is the maximum number of stereoisomers possible for artemisinin?
  4. How are the N atoms in mefloquine hybridized?
  5. Can two molecules of artemisinin intermolecularly hydrogen bond to each other?
  6. What product is formed when mefloquine is treated with HCl?

Rank the following groups in order of decreasing priority.

  1. -F,-NH2,-CH3,-OH
  2. -CH3,-CH2CH3,-CH2CH2CH3,-(CH2)3CH3
  3. -NH2,-CH2NH2,-CH3,-CH2NHCH3
  4. -COOH,-CH2OH,-H,-CHO
  5. -Cl,-CH3,-SH,-OH
  6. -C≡CH,-CH(CH3)2,-CH2CH3,-CH=CH2
See all solutions

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