The product of the following reaction gave 6 line ¹³ C NMR spectrum with peaks at δ 175,52,50,46,37,33 ppm… · ABC26OR0733
Subject: Organic Chemistry · Chapter: Organic Spectroscopy · Topic: Organic Spectroscopy – General · Exam: GATE 2000-2022 · Marks: 2 · Difficulty: Medium
The product of the following reaction gave 6 line ${ }^{13} \mathrm{C}$ NMR spectrum with peaks at $\delta 175,52,50,46,37,33$ ppm. The structure of the product is 
(a)
(b)
(c)
(d)
Answer
Answer: C ✓ checked by 4AB · confidence high
Explanation
Photochemical Wolff rearrangement of the α-diazoketone contracts the norbornanone to the bicyclo[2.1.1]hexane ketene, trapped by MeOH as the ester (c); six ¹³C lines (175 ester C=O, 52 OMe, 50, 46, 37, 33) fit this symmetric ester.
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