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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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Answer

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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

Compound X is optically inactive and has the formulaC16H16Br2. On treatment with strong base, X gives hydrocarbon Y,C16H14. Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst and reacts with ozone to give two fragments. One fragment, Z, is an aldehyde with formulaC7H6O. The other fragment is glyoxal,(CHO)2. Write the reactions involved, and suggest structures for X, Y, and Z. What is the stereochemistry of X?

Propose a mechanism for the following reaction, an important step in the laboratory synthesis of proteins:

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

Which reactant in each of the following pairs is more nucleophilic? Explain.

(e) I- or Cl-

What stereochemistry do you expect for the trisubstituted alkene obtained by E2 elimination of the following alkyl halide on treatment with KOH? (Reddish brown = Br.)
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