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Question: Which of the following represents decreasing order of reactivity of given organic compounds towards ...

Which of the following represents decreasing order of reactivity of given organic compounds towards nitration?

A

IV > V > II > III > I

B

I > II > III > V > IV

C

III > I > III > V > IV

D

V > IV > II > III > I

Answer

IV > V > II > III > I

Explanation

Solution

  1. Substituent Effects:

    • Methyl (–CH₃): +I, activates the aromatic ring.
    • Carboxyl (–COOH): –I, deactivates the aromatic ring.

  2. Analysis of Compounds:

    • p‑xylene (IV): Two activating methyl groups (at para positions) → most activated.
    • m‑xylene (V): Two methyl groups present but less efficiently synergistic than in para configuration → slightly less reactive than (IV).
    • Toluene (II): One methyl group (activating) → less reactive than di‑substituted xylenes.
    • p‑Toluic acid (III): One methyl (activating) and one COOH (deactivating) → net lower reactivity than toluene.
    • Terephthalic acid (I): Two COOH groups (strongly deactivating) → least reactive.

  3. Decreasing Order of Reactivity: → IV > V > II > III > I