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Chapter 11: Q49bE (page 350)

Question: Propose structures for compounds that fit the following descriptions:

(b) An organohalide that will not undergo nucleophilic substitution

Short Answer

Expert verified

Answer:

CH2=CHBrlike other in vinylic organohalide do not show the nucleophilic substitution

Step by step solution

01

SN1 reaction

It is a nucleophilic substitution reaction in which an old bond is broken and a new bond is formed both processes occur simultaneously. Hence, it鈥檚 a single-step reaction.

The two reacting species are involved in the rate-determining steps.

02

E2 reaction

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

Here, the carbon-hydrogen or halogen bond breaks to form a new double bond. Hence, it鈥檚 a single-step reaction.

03

Formation of alkene

Organohalide is the vinylic halide that already has a double bond so these compounds do not show any nucleophilic substitution reactions.

LikeCH2=CHBr

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Most popular questions from this chapter

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

(d) NaCN

Write the product you would expect from reaction of each of the following alkyl halides with (1)Na+-SCH3and (2)Na+-OH (green = Cl):

b)

Which reaction in each of the following pairs would you expect to be faster?

(c) TheSN2displacement on 2-bromopropane by鈥�CH3CH2O-or byCN-

The following Walden cycle has been carried out. Explain the results, and indicate where Walden inversion occurs.

SN2 reactions take place with inversion of configuration, andSN1 reactions take place with racemization. The following substitution reaction, however, occurs with complete retention of configuration. Propose a mechanism.

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