Single Choice

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

Acabanion
Bcarbene
Cfree-radical
Dcarbocation
Correct Answer

Solution

A planar cabocation is generated when $$Sb{Cl}_{5}$$ remove $${Cl}^{-}$$ from the substrate.

Since the reactant is having chiral center.

This carbocation is subsequently attacked by $${Cl}^{-}$$ (nucleophile) from both the sides (ie., from top and bottom) to produce a racemic mixture.

Option D is correct.

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

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

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

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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