Single Choice

In a nucleophilic substitution reaction: $$R-Br+Cl^-\xrightarrow{DMF}R-Cl+Br^-$$ Which one of the following undergoes complete inversion of configuration?

A$$C_6H_5CHC_6H_5Br$$
B$$C_6H_5CH_2Br$$
C$$C_6H_5CH CH_3Br$$
Correct Answer
D$$C_6H_5CCH_3C_6H_5Br$$

Solution

In the compound of option B, bromine is attached to a primary carbon atom. The substitution occurs via $$SN_2$$ mechanism which involves the inversion of configuration.
In the remaining compounds the bromine is attached to a secondary or tertiary carbon atom. In case of secondary carbon atom (options A and C), the substitution occurs via a combination of $$SN_1$$ and $$SN_2$$ mechanisms. Hence, complete inversion of configuration is not possible.
In case of tertiary carbon atom, (option D) the substitution occurs via $$SN_1$$ mechanism which cannot result in complete inversion of configuration.

SIMILAR QUESTIONS

Haloalkanes and Haloarenes

Which of the following is not stereospecific?

Haloalkanes and Haloarenes

Write $$SN^1$$ mechanism for the hydrolysis of tert-butyl bromide.

Haloalkanes and Haloarenes

Explain $${ S }_{ N }{1 }$$ mechanism with an example.

Haloalkanes and Haloarenes

$$S_{N}1$$ reactions are accompanied by racemization in optically active alkyl halides. Why?

Haloalkanes and Haloarenes

Which statement is correct about the above reaction?

Haloalkanes and Haloarenes

Which statement is correct about the following reaction?

Haloalkanes and Haloarenes

(-)-1-chloro-1-phenylethane in toluene racemises slowly in the presence of small amount of $$Sb{Cl}_{5}$$, due to the formation of:

Haloalkanes and Haloarenes

Which of the following halides will be most reactive in $${ SN }^{ 2 }$$ reaction and $${ SN }^{ 1 }$$ reaction, respectively ?

Haloalkanes and Haloarenes

Sec-Butyl alcohol will undergo alkaline hydrolysis in the polar solvent by:

Haloalkanes and Haloarenes

Which of the following gives $$SN^{1}$$ reaction?

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