Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 5, Problem 44P

Compound F has the molecular formula C 5 H 8 and is optically active. On catalytic hydrogenation F yields G ( C 5 H 12 ) (and G is optically inactive. Propose structures for F and G.

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3. An optically active compound A has the molecular formula C6H140. This compound reacts with Na2Cr207 in sulfuric acid to form a new optically active compound B, with the molecular formula C,H12O. Suggest structures for A and B.
Using the isomers classification flowchart given above, categorize each pair of structures using all the terms that apply: Identical, isomers, constitutional isomers, conformational isomers (name type), stereoisomers, enantiomers or diastereomers. (a) (b) O (d) C -off-as and H (f) and and and H OH H₂C H₂C H₂C H₂C H its - outs and WOCH, OCH, X-X and OH OH
Compound A (C5H8) readily reacts with bromine (Br2) at room temperature to discharge the purple colour of bromine and form Compound B ‍‍(C5H8Br2). When Compound A is treated with H2 in the presence of a transition metal catalyst, it is converted to compound C ‍(C5H10). When treated with HCl, compound A is converted to compound D (C5H9Cl)‍‍. B, Cand D are saturated compounds. Given this information, propose structural formulas for compounds A, B, C, and D.

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Organic Chemistry

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