Q10(a). Reformatsky reaction and dehydration; Doebner synthesis
Write the structure of final products (P and Q) in the following reactions: (i) [aryl ketone + α-bromo ester] with i) Zn, THF, 60 °C; ii) HCl, THF → P; (ii) [aromatic amine + aromatic aldehyde + pyruvic acid] in EtOH, Δ → Q. [structures given in the paper]
Answer in brief
P = methyl 2-(6-methoxy-1H-inden-3-yl)butanoate; Q = 6-methoxy-2-(3-nitrophenyl)quinoline-4-carboxylic acid.
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CoversReformatsky reactionzinc enolateDoebner reactionquinoline-4-carboxylic acidβ-hydroxy ester dehydration
All parts of Question 10
- 10(a) Reformatsky reaction and dehydration; Doebner synthesis10 marks
- 10(b) Electronic transitions of acrylaldehyde; hexane to ethanol5 marks
- 10(c) Thermal [1,3] shift: hydrogen cannot migrate, carbon can5 marks
- 10(d) Spectral structure problem: the liquid from acetone and base10 marks