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Chapter 9: Q18P (page 409)

Draw the stereoisomers that are formed from the following SN1 reactions:

a. 3-bromo-3-methylpentane and methanol

b. 3-chloro-3-methylhexane and methanol

Short Answer

Expert verified

The produced stereoisomers are:

Step by step solution

01

Definition of SN1 reaction

SN1 reaction is a substitution reaction which proceeds through forming a carbocation as an intermediate and nucleophilic attack happens in the 2nd step. It is not a concerted mechanism and rate of the reaction depends only on the concentration of the alkyl halide.

02

Reaction mechanism

Reaction mechanism of SN1 reaction is given below,

03

Stereoisomers

The stereoisomers that are formed in both reactions are given below,

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Most popular questions from this chapter

Methoxychlor is an insecticide that was intended to take DDT’s place because it is not as soluble in fatty tissues and is more readily biodegradable. It, too, can accumulate in the environment, however, so its use was also banned—in 2002 in the European Union and in 2003 in the United States. Why is methoxychlor less soluble in fatty tissues than DDT?

a. What is the major product obtained when each of the following compounds undergoes an E2 reaction with methoxide ion ? Show the configuration of the product.

b. Does the product obtained depend on whether you start with the R or S enantiomer of the reactant?

Which reaction in each of the following pairs takes place more rapidly?

a. Which reacts faster in an SN2 reaction?

b.Which reacts faster in an E1 reaction?

c.Which reacts faster in an SN1 reaction?

Four alkenes are formed from the E1 reaction of 3-bromo-2,3-dimethylpentane and methoxide ion. Draw the structures of the alkenes and rank them according to the amount that would be formed.
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