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Question
Which of the following compounds will most readily undergo electrophilic aromatic substitution ?
Which of the following compounds will most readily undergo electrophilic aromatic substitution ?
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Solution
The correct option is C
Rate of electrophilic substitution reaction is proportional to the stability of the carbocation intermediate (Arenium ion) formed in the reaction.
In (a), there is no any stabilisation for the carbocation formed.
In (b), Cl is an electron withdrawing group so it will destabilise the carbocation formed.
In (c), OH group will stabilise the carbocation formed because OH is a +R group which will donate the electron pair and stabilise the arenium ion formed.
In (d), the carbocation is stabilised by CH3 which shows hyperconjugation effect.
Comparing (c) and (d), compound (c) is more stabilised because resonance effect is prior to hyperconjugation effect.
Hence, compound (c) will be easily attacked by an electrophile.
Rate of electrophilic substitution reaction is proportional to the stability of the carbocation intermediate (Arenium ion) formed in the reaction.
In (a), there is no any stabilisation for the carbocation formed.
In (b), Cl is an electron withdrawing group so it will destabilise the carbocation formed.
In (c), OH group will stabilise the carbocation formed because OH is a +R group which will donate the electron pair and stabilise the arenium ion formed.
In (d), the carbocation is stabilised by CH3 which shows hyperconjugation effect.
Comparing (c) and (d), compound (c) is more stabilised because resonance effect is prior to hyperconjugation effect.
Hence, compound (c) will be easily attacked by an electrophile.
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