One or more options correct
Aromatic substitution and its limitations are used in the following statements. The CORRECT statement(s) is/are
- A. Friedel-Crafts alkylation of benzene with -chloropropane and anhydrous gives mainly isopropylbenzene, because the primary carbocation-like species rearranges by a hydride shift.
- B. Nitrobenzene undergoes Friedel-Crafts acylation with at the meta position in good yield.
- C. Acylation of benzene with propanoyl chloride/ followed by Clemmensen reduction gives -propylbenzene free from isopropylbenzene.
- D. Nitration of chlorobenzene with gives mainly -chloro--nitrobenzene, since is an electron-withdrawing group.
Show answer and solution
Answer: A, C
(A) With the incipient primary cation undergoes a 1,2-hydride shift to the more stable secondary cation, which alkylates benzene, so isopropylbenzene (cumene) predominates: correct. (B) A nitro group strongly deactivates the ring (and complexes with ), so nitrobenzene does not undergo Friedel-Crafts reactions at all: wrong. (C) The acylium ion does not rearrange; it gives propiophenone, . Clemmensen reduction () converts to , giving -propylbenzene with no isopropyl isomer: correct. (D) Chlorine withdraws electrons by the effect, which deactivates the ring, but its lone pairs donate by , which directs the incoming nitronium ion ortho and para. The major products are -chloro--nitro and -chloro--nitrobenzene: wrong.
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