Q4(c)(i). Benzoin exchange in cyanide
Give products and mechanism when benzoin and p-anisaldehyde are heated with KCN.
Answer in brief
Cyanide permits retro-benzoin cleavage and crossed benzoin formation; with Ar = p-MeOC₆H₄, the crossed products are PhCOCH(OH)Ar and ArCOCH(OH)Ph.
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Coversbenzoin condensationcrossed benzoinretro-benzoinumpolungcyanide catalysis
All parts of Question 4
- 4(a) Grignard addition and competing reduction10 marks
- 4(b) Stobbe condensation10 marks
- 4(c)(i) Benzoin exchange in cyanide10 marks
- 4(c)(ii) Bischler–Napieralski cyclization10 marks