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Question
Why haloarenes are not reactive towards nucleophilic substitution reaction? Give two reactions.
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Solution
Haloarenes are not reactive towards nucleophilic substitution reactions because of two reasons:
- The difference in the hybridisation of carbon atoms is the bond.
- Instability of phenyl cation.
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RELATED QUESTIONS
Chlorobenzene is extremely less reactive towards a nucleophilic substitution reaction. Give two reasons for the same.
Write the final product(s) in each of the following reactions:
The presence of nitro group (−NO2) at o/p positions increases the reactivity of haloarenes towards nucleophilic substitution reactions.
How the following conversion can be carried out?
Chlorobenzene to p-nitrophenol
What is Grignard reagent?
Which of the following compounds will give racemic mixture on nucleophilic substitution by \[\ce{OH-}\] ion?
(a) \[\begin{array}{cc}
\phantom{}\ce{CH3 - CH - Br}\\
\phantom{}|\\
\phantom{....}\ce{C2H5}\phantom{}
\end{array}\]
(b) \[\begin{array}{cc}
\phantom{..}\ce{Br}\\
\phantom{}|\\
\phantom{}\ce{CH3 - C - CH3}\\
\phantom{}|\\
\phantom{....}\ce{C2H5}\phantom{}
\end{array}\]
(c) \[\begin{array}{cc}
\phantom{....}\ce{CH3 - CH - CH2Br}\\
\phantom{}|\\
\phantom{....}\ce{C2H5}\phantom{}
\end{array}\]
Arrange the following compounds in increasing order of rate of reaction towards nucleophilic substitution.
| (a) |  |
| (b) |  |
| (c) |  |
Arrange the following compounds in increasing order of rate of reaction towards nucleophilic substitution.
| (a) |  |
| (b) |  |
| (c) |  |
Haloarenes are less reactive than haloalkanes and haloalkenes. Explain.
Assertion: Chlorobenzene is resistant to nucleophilic substitution reaction at room temperature.
Reason (R): C–Cl bond gets weaker due, to resonance.
