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Chapter 11: Q.11-50b (page 350)

Question:What products would you expect from the reaction of 1-bromopropane with each of the following?

(b) KOC(CH3)

Short Answer

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Answer

CH3CH2CH2Br+KOC(CH3)2→HOC(CH3)2+CH3CH2CH2OC(CH3)2+KBrEliminationreactionCH3CH2CH2Br+KOC(CH3)2→CH3CH=CH2+KBrSubstitutionreaction

Step by step solution

01

SN2 reaction

It is a nucleophilic substitution reaction in which old bond is broken and a new bond is formed. Both the processed occur simultaneously. Hence, it is a single step reaction.

Two reacting species are involved in the rate determining steps.

CH3CH2CH2Br+KOC(CH3)2→CH3CH=CH2+KBrSubstitutionreaction

02

E2 reaction

It is a nucleophilic elimination reaction in which old bond is broken and a new bond is formed. Both the processes occur simultaneously and no intermediate is formed.

Here, carbon hydrogen or halogen bond break to form new double bond. Hence, it’s a single step reaction.

CH3CH2CH2Br+KOC(CH3)2→HOC(CH3)2+CH3CH2CH2OC(CH3)2+KBrEliminationreaction

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Most popular questions from this chapter

How might you prepare each of the following molecules using a nucleophilic substitution reaction at some step?

(a)

Question: Review the mechanism of geraniol biosynthesis shown in Figure 11-15, and propose a mechanism for the biosynthesis of limonene from linalyl diphosphate.

What effect would you expect the following changes to have on the reaction rate of 1-iodo-2-methylbutane with cyanide ion?

(a) TheCN-concentration is halved, and the 1-iodo-2-methylbutane concentration is doubled.

(b) Both theCN-and the 1-iodo-2-methylbutane concentrations are tripled.

What effect would you expect the following changes to have on the rate of thereaction of 1-iodo-2-methylbutane with cyanide ion?

(b) Both theand the 1-iodo-2-methylbutane concentrations are tripled.

Question: Arrange the carbocations below in order of increasing stability.

a.
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