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Chapter 11: Q47aE (page 350)

Question: Predict the product and give the stereochemistry resulting from reaction of each of the following nucleophiles with (R)-2-bromooctane:

a) CN-

Short Answer

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Answer

Step by step solution

01

SN2 reaction

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

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

02

 Definition of Nucleophile and Stereochemistry

Nucleophiles are the negatively charged ions or the neutral species having the lone pair of electrons that are ready for bonding.

Stereochemistry - It is a study of the arrangement of atoms in a space that forms a molecule.

03

Species react faster with 2-bromoctane

2-bromoctane is a secondary bromoalkane so the reaction proceeds with the inversion of configuration that the chirality of the carbon atom is changed as shown:

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Most popular questions from this chapter

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

(c) NaI

Tell whether each of the following reactions is likely to be SN1, SN2, E1, E1cB or E2:

c)

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

(d) Thedisplacement byon bromomethane in benzene or in acetonitrile

We saw in Section 8-7 that bromohydrins are converted into epoxides when treated with base. Propose a mechanism, using curved arrows to show the electron flow.
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