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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

(S)-2-Butanol slowly racemizes on standing in dilute sulfuric acid. Explain.

What product would you expect from SN2reaction of 1-bromobutane with each of the following?

(a)NaI (b) KOH (c)H—C≡C—Li(d)NH3

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

c)

Question: The reactions shown below are unlikely to occur as written. Tell what is wrong with each, and predict the actual product.

a.

Question: Ignoring double-bond stereochemistry, what products would you expect from elimination reactions of the following alkyl halides? Which product will be the major product in each case?
See all solutions

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