b) A compound with molecular formula C,H1402 upon hydrolysis produces an alcohol and an acid. It has the following NMR data : 'H-NMR (at 298 K, 600 MHz, CDC13) : 80-92 (d, 6H), 1-52 (т, 2н), 1-69 (m, 1H), 2-04 (s 3H) and 4-09 (t, 2H). 13 C-NMR : 8 21-0, 22:5, 25·1, 37.4, 63·1 and 171-2 ppm DEPT provided two inverted signals. Predict the structure of the alcohol that is obtained through hydrolysis of the mentioned parent compound. Assign appropriate IR values, 'H and 13C-NMR resonances along with a mass spectral pattern for the alcohol.
b) A compound with molecular formula C,H1402 upon hydrolysis produces an alcohol and an acid. It has the following NMR data : 'H-NMR (at 298 K, 600 MHz, CDC13) : 80-92 (d, 6H), 1-52 (т, 2н), 1-69 (m, 1H), 2-04 (s 3H) and 4-09 (t, 2H). 13 C-NMR : 8 21-0, 22:5, 25·1, 37.4, 63·1 and 171-2 ppm DEPT provided two inverted signals. Predict the structure of the alcohol that is obtained through hydrolysis of the mentioned parent compound. Assign appropriate IR values, 'H and 13C-NMR resonances along with a mass spectral pattern for the alcohol.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...
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