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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-

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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鈥檚 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

3-Bromo-1-butene and 1-bromo-2-butene undergoSN1 reaction at nearly the same rate, even though one is a secondary halide and the other is primary. Explain.

What product would you expect to obtain from SN2 reaction of OH-with (R)-2-bromobutane? Show the stereochemistry of both the reactant and product.

Organic solvents like benzene, ether, and chloroform are neither protic nor strongly polar. What effect would you expect these solvents to have on the reactivity of a nucleophile in SN2 reactions?

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

Assign R or S configuration to the following molecule, write the product you would expect from SN2reaction with NaCN, and assign R or S configuration to the product (green = Cl):
See all solutions

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