Q19 · CSIR-NET Chemistry, June 2011
Paper: CSIR-NET June 2011 · Subject: Organic Chemistry · Chapter: Natural Products · Topic: Natural Products – General · Marks: 2 · Difficulty: Medium
Under review — part of this question (a structure or an option) is not clear in the source scan. 4AB is checking it against the original book; the answer shown may change.
Papaverine on oxidation with potassium permanganate gives a ketone, which on fusion with potassium hydroxide gives 
Papaverine
Papaverine(a)
(b)
(c)
(d)
Answer
Under review — not yet confirmed.
Answer: B
Answer: (b) and (c) — veratric acid (as its K salt) and 6,7-dimethoxyisoquinoline.
Explanation
Answer: (b) and (c) — veratric acid (as its K salt) and 6,7-dimethoxyisoquinoline — KMnO₄ oxidises the CH₂ bridge of papaverine to the ketone papaveraldine. KOH fusion cleaves the aryl ketone into potassium 3,4-dimethoxybenzoate and 6,7-dimethoxyisoquinoline.
Study loop for Natural Products