The increasing order of reactivity of the following compounds towards aromatic electrophilic substitution reaction is:

09.04.2019 Shift 1 Synergy JEE Mains D75

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  1. D < A < C < B
  2. B < C < A < D
  3. A < B < C < D
  4. D < B < A < C

Answer (Detailed Solution Below)

Option 1 : D < A < C < B
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JEE Main 04 April 2024 Shift 1
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Detailed Solution

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Concept:

  • Electrophilic aromatic substitution (EAS) is where benzene acts as a nucleophile to replace a substituent with a new electrophile. That is, benzene needs to donate electrons from inside the ring. An electrophile attacks the region of high electron density.
  • Activating group is that which increases the rate of an electrophilic aromatic substitution reaction, relative to hydrogen.CH3 is a perfect example of an activating group; when we substitute a hydrogen on benzene for CH3, the rate of nitration is increased.
  • A deactivating group, on the other hand, decreases the rate of an electrophilic aromatic substitution reaction, relative to hydrogen. The trifluoromethyl group, F3, drastically decreases the rate of nitration when substituted for a hydrogen on benzene.
  • This definition is ultimately based on experimental reaction rate data.  It doesn’t tell us why each group accelerates or decreases the rate. “Activating” and “deactivating” just refers to the effect of each substituent on the rate, relative to H.
  • CH3 is an activating group because of its +I effect, −Cl and −NO2 are deactivating due to their −I and −M effect. −CH3 group, having +I effect, increases the electron density in the benzene ring whereas −Cl group having −I effect decreases the electron density the benzene ring.

Calculation:

→ Order of strength for electrophilic substitution

+ M > + I > - I > - M

→ SE ∝ EDG

\(SE \propto \frac{1}{{EWG}}\)

Where, EDG is Electron Drawing Group,

EWG is Electron Withdrawing Group

09.04.2019 Shift 1 Synergy JEE Mains D76

→ Thus, the increasing order of reactivity of the given compounds towards aromatic electrophilic substitution reaction is

D (-M) < A (-I) < C (+I) < B (+M)

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