Indian Forest Service (Mains), Chemistry optional · 2021 · Paper II
Q6(c)(i). Cyclization of a beta-hydroxy phenethylamide
Question
Identify A and B from PhCH(OH)CH₂NH₂ treated with one equivalent of acetic anhydride, then POCl₃; give the mechanism.
Answer in brief
A is N-(2-hydroxy-2-phenylethyl)acetamide; cyclodehydration gives 1-methylisoquinoline B.
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CoversPictet–Gams reactionBischler–Napieralski reaction1-methylisoquinolinePOCl₃ cyclodehydrationisoquinoline synthesis
All parts of Question 6
- 6(a)(i) Malonic ester ring synthesis5 marks
- 6(a)(ii) Wittig olefination5 marks
- 6(b)(i) Tertiary protein structure5 marks
- 6(b)(ii) End-group content of polystyrene5 marks
- 6(c)(i) Cyclization of a beta-hydroxy phenethylamide5 marks
- 6(c)(ii) Terylene from p-xylene5 marks
- 6(d) Fischer indole synthesis5 marks
- 6(e) Acid equivalent of nylon-6,65 marks