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Chapter 10: PROBLEM 10.51 (page 422)

Question: Draw all stereoisomers formed in each reaction.

a.

b.

c.

Short Answer

Expert verified

Answer

a,

b.

c.

Step by step solution

01

Geometrical isomers  

The geometrical isomers are also stereoisomers. They show cis-trans geometry. If two substituents have the same stereochemistry, cis isomers are formed and vice versa for trans isomers.

02

Optical isomers  

Optical isomers are also stereoisomers that have chiral centers but lack a plane of symmetry. If two compounds with the same molecular formula have opposite stereochemistry, they form stereoisomers.

03

Explanation

a. The bromination of the alkene substrate allows the trans addition of bromine atoms on the sides of the double bond.

Stereoisomers obtained from a

b. The chlorination of the alkene substrate allows the trans addition of the chlorine atom and the hydroxide ion on the sides of the double bond.

Stereoisomers obtained from b

c. In the presence of DMSO and water, NBS allows trans addition on the double bond.

Stereoisomers obtained from c

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Most popular questions from this chapter

Question: Draw the six alkenes of the molecular formula C5H10. Label one pair of diastereomers.

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a

b.

c.

Question: What alkene can be used to prepare each alkyl halide or dihalide as the exclusive or major product of an addition reaction?

a.

b.

c.

d.

Question: Give the structure corresponding to each name.

a. (E)-4-ethylhept-3-ene

b. 3,3-dimethylcyclopentene

c. 4-vinylcyclopentene

d. (Z)-3-isopropylhept-2-ene

e. cis-3,4-dimethylcyclopentene

f. 1-isopropyl-4-propylcyclohexene

g. 3,4-dimethylcyclohex-2-enol

h. 3,5-diethylhex-5-en-3-ol
See all solutions

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