One or more options correct
Which of the following transformations of aromatic compounds give the stated major product?
- A. Benzene ethylbenzene
- B. Nitrobenzene -nitrotoluene
- C. Aniline exclusively -nitroaniline
- D. Phenol -hydroxybenzaldehyde as the major product
Show answer and solution
Answer: A
(A) Correct. Friedel-Crafts acylation gives acetophenone, which the Clemmensen reduction converts to ethylbenzene; acylation is used because direct alkylation with ethyl halide could rearrange or poly-alkylate. (B) Incorrect. The strongly deactivating group makes nitrobenzene unreactive in Friedel-Crafts alkylation, and the also complexes with it. (C) Incorrect. In strongly acidic medium aniline is protonated to the anilinium ion, a meta director, so a large amount of -nitroaniline is formed together with oxidation products; the product is not exclusively para. (D) Incorrect. In the Reimer-Tiemann reaction the electrophilic dichlorocarbene attacks the ortho position of the phenoxide, so salicylaldehyde is the major product and the para isomer is minor.
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