[1] CH3LI Y [2] CH3I H NMR of Y 6 H 2H 2H 3H 1H 8 6 5 4 3 ppm

EBK A SMALL SCALE APPROACH TO ORGANIC L
4th Edition
ISBN:9781305446021
Author:Lampman
Publisher:Lampman
Chapter31: An Oxidation–reduction Scheme: Borneol, Camphor, Isoborneol
Section: Chapter Questions
Problem 2Q
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Treatment of W with CH3Li, followed by CH3I, affords compound Y
(C7H14O) as the major product. Y shows a strong absorption in its IR
spectrum at 1713 cm−1, and its 1H NMR spectrum is given below. (a)
Propose a structure for Y. (b) Draw a stepwise mechanism for the
conversion of W to Y.

[1] CH3LI
Y
[2] CH3I
H NMR of Y
6 H
2H
2H
3H
1H
8
6
5
4
3
ppm
Transcribed Image Text:[1] CH3LI Y [2] CH3I H NMR of Y 6 H 2H 2H 3H 1H 8 6 5 4 3 ppm
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