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Chapter 11: Q48E (page 350)

Question: (R)-2-Bromooctane undergoes racemization to give (卤)-2-bromooctane when treated with NaBr in dimethyl sulfoxide. Explain.

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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鈥檚 a single-step reaction.

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 that are ready for bonding.

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

03

Chemical reaction

When the 2 bromooctane react 50% then leads to the formation of 50% of R and 50% of S in the reaction. Thus, the reacting species is completely racemized.

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