organic compound B with formula C6H14O has the following: IR Spectroscopy      2974 cm-1, 1080 cm-1 Mass Spectrometry       102 (M+), 87, 73 1H NMR Spectroscopy    Eight signals at δ 1.10 (d, 3H), 1.13 (dd, 3H), 1.14 (dd, 3H), 1.59 (ddq, 1H), 1.60 (ddq, 1H), 3.19 (ddq, 1H), 3.51 (dq, 1H), 3.50 (dq, 1H). Compound B is obtained by the reaction of compound A with

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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An organic compound B with formula C6H14O has the following:

IR Spectroscopy      2974 cm-1, 1080 cm-1

Mass Spectrometry       102 (M+), 87, 73 1H

NMR Spectroscopy    Eight signals at δ 1.10 (d, 3H), 1.13 (dd, 3H), 1.14 (dd, 3H), 1.59 (ddq, 1H), 1.60 (ddq, 1H), 3.19 (ddq, 1H), 3.51 (dq, 1H), 3.50 (dq, 1H).

Compound B is obtained by the reaction of compound A with NaH followed by CH3CH2Br. The stereochemistry of A is "S" 


Using this information, deduce a plausible structure for Compound A with correct stereochemistry.

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