Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
12th Edition
ISBN: 9780357391594
Author: Frederick A. Bettelheim; William H. Brown; Mary K. Campbell
Publisher: Cengage Learning US
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Chapter 14, Problem 37P

15-41 Compound A(C5Hh, is not optically active and cannot be separated into enantiomers. It reacts with bromine in carbon tetrachloride to discharge the purple color of bromine and form Compound B( C.FL Br,). When Compound A is treated with H., in the presence of a transition metal catalyst, it is converted to compound C(C5H10). When treated with HC1, compound A is converted to compound DtC.HyCl). Given this information, propose structural formulas for compounds A B, C, and D. Hint: There are at least three possibilities for Compound A and, in turn, three possibilities for Compounds B. C, and D.

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