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Q.

What is the correct increasing order of reactivity of the following compounds towards electrophilic aromatic substitution reaction?

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a

IV < III < I<II

b

III < IV < I<II

c

I < II < III < IV

d

IV < III < II <I

answer is B.

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Detailed Solution

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Electron donating groups increase the reactivity of benzene ring towards electrophilic aromatic substitution while electron withdrawing groups decrease the reactivity.

-CH3 is an electron donating and an ortho para directing group while -F and -CHO are electron withdrawing groups.

Compound I contain -CH3 groups at 1 and 3 positions allowing the incoming electrophile to attack in ortho positions.

Compound II contains -CH3 groups at 1 and 4 positions. Thus, the incoming electrophile is not available to bind with benzene at ortho and para positions as two methyl groups repel each other in their ortho para directing effect.

-F is highly electronegative compared to carbonyl group, leading to its more electron withdrawing nature.

Thus, the increasing order of reactivity of the following compounds towards electrophilic aromatic substitution reaction is: IV < III < II <I

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