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Chapter 11: Q47cE (page 350)

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

(c)CH3S-

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Answer

Step by step solution

01

SN2 reaction

This is a nucleophilic substitution reaction in which an old bond is broken and a new bond is formed simultaneously. The response is one-step because there is only one bond to form.

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

02

Definition of Nucleophiles and Stereochemistry

Nucleophiles are the negatively charged ions or the neutral species having the lone pair of electrons 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

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

When primary alcohol is treated with p-toluenesulfonyl chloride at room temperature in the presence of an organic base such as pyridine, a tosylate is formed. When the same reaction is carried out at a higher temperature, an alkyl chloride is often formed. Explain.

Assign configuration to the following substrate, and show the stereochemistry and identity of the product you would obtain by reaction with water (reddish-brown=Br):

Question: There are eight diastereomers of 1,2,3,4,5,6-hexachlorocyclohexane. Draw each in its more stable chair conformation. One isomer loses HCl in an E2 reaction nearly 1000 times more slowly than the others. Which isomer reacts so slowly, and why?

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

(a) TheSN2displacement byI-鈥�on鈥�CH3Cl鈥�or鈥�CH3OTs
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