World of Chemistry, 3rd edition
3rd Edition
ISBN:9781133109655
Author:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCoste
Chapter2: Matter
Section: Chapter Questions
Problem 7STP
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Reaction of unknown A with HCl forms chlorohydrin B as the major product. A shows no absorptions in its IR spectrum at 1700 cm−1 or 3600-3200 cm−1, and gives the following 1H NMR data: 1.4 (doublet, 3 H), 3.0 (quartet of doublets, 1 H), 3.5 (doublet, 1 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.2 (doublet, 2 H) ppm. (a) Propose a structure for A, including stereochemistry. (b) Explain why B is the major product in this reaction.
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