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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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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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Most popular questions from this chapter

Which compound in each of the following pairs will react faster in an SN2reaction with OH-?

(c)(CH3)3CClorCH3Cl

Question: Order each of the following sets of compounds with respect to reactivity:

b. (CH3)3 CCI (CH3)3 CBr (CH3)3 COH

Rank the following compounds in order of their expected reactivity toward SN2reaction:

CH3Br,CH3OTos,CH33CCl,CH32CHCl

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

(a)NaI (b) KOH (c)H鈥�C鈮�C鈥�Li(d)NH3

Question: Propose structures for compounds that fit the following descriptions:

(b) An organohalide that will not undergo nucleophilic substitution

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