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Chapter 7: PROBLEM 7.60 (page 292)

Question: Draw the products of each SN1 reaction and indicate the stereochemistry when necessary.

a.

b.

Short Answer

Expert verified

a.

Products obtained from reaction (a)

b.

Products obtained from reaction (b)

Step by step solution

01

Stereochemistry of the SN1 reactions

The SN1 reaction takes place in two steps. The first step involves the formation of the carbocation intermediate with the removal of the leaving group. The nucleophile attacks in the second step.

The carbocation intermediate is achiral in nature, and it has a planar geometry. The nucleophilic attack can take place from both sides of the intermediate.

This results in the formation of equal amounts of the two enantiomeric products, and the racemic mixture is obtained.

02

The products of the given reaction are as follows:

a. The given reactants will produce a racemic mixture of the following products:

Products obtained from reaction (a)

b.The given reactants will produce a racemic mixture of the following products:

Products obtained from reaction (b)

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Most popular questions from this chapter

Question: Give the structure corresponding to each name.

a. 3-chloro-2-methylhexane

b. 4-ethyl-5-iodo-2,2-dimethyloctane

c. cis-1,3-dichlorocyclopentane

d. 1,1,3-tribromocyclohexane

e. sec-butyl bromide

f. 6-ethyl-3-iodo-3,5-dimethylnonane

Question: Rank the nucleophiles in each group in order of increasing nucleophilicity.

a. OH-,NH2- , H2O

b. OH- ,Br- , F-(polar aprotic solvent)

c. H2O, OH-,CH3CO2-

Question: Which compound in each pair undergoes a faster SN2 reaction?

a.

and

b.

and

Question: Muscalure, the sex pheromone of the common housefly, can be prepared by a reaction sequence that uses two nucleophilic substitutions. Identify compounds A–D in the following synthesis of muscalure.

Question: Which solvents favor SN1reactions and which favor SN2 reactions?

a.

b. CH3CN

c.

d.
See all solutions

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