Question:
$ t- $ butyl chloride preferably undergo hydrolysis by
$ t- $ butyl chloride preferably undergo hydrolysis by
Updated On: Jul 28, 2022
- $ {{S}_{N}}1 $ mechanism
- $ {{S}_{N}}2 $ mechanism
- Any of (a) and (b)
- None of the above
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The Correct Option is A
Solution and Explanation
Tertiary halide preferentially undergo $ {{S}_{N}}1 $ substitution as they can give stable carbocation. $ \underset{t-butyl\,\,chloride}{\mathop{{{H}_{3}}C-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-Cl}}\,\xrightarrow[-Cl]{slow}\underset{\begin{smallmatrix} {{3}^{o}}carbocation \\ (most\,\,stable) \end{smallmatrix}}{\mathop{{{({{H}_{3}}C)}_{3}}{{C}^{+}}}}\,\xrightarrow[fast]{+O{{H}^{-}}} $ $ \underset{t-butyl\,\,alcohol}{\mathop{{{({{H}_{3}}C)}_{3}}COH}}\, $
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Concepts Used:
Preparation of Haloalkanes
- Preparation by Alcohols: By using alcohol, we can very easily prepare Haloalkane as when R-OH is reacted with a suitable reagent it will form R-X. The following reagents will help in the formation of the reactions:
- Halogen Acids (HX)
- Thionyl chloride (SOCl2)
- Phosphorous halides (PX5 or PX3)
- Preparation by Free Radical Halogenation: The formation of alkyl bromides and alkyl chloride is very much possible with the help of free radical halogenation, but as these radicals are highly reactive and non-specific in nature, they can result in the formation of a mixture of products. Though, it's not a preferred method for the preparation of haloalkanes. For example, free radical chlorination can result in the formation of a number of haloalkanes, which in turn makes it difficult to set apart a single product.
- Preparation by Alkenes: An electrophilic addition reaction can be used to transform an alkene into a haloalkane as alkene will react with HX to form R-X.
Read More: Haloalkanes and Haloarenes