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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Compound B contains one chiral carbon atom and reacts with concentrated H2SO4 to yield compounds and G (both CSH10) that are positional isomers of each other (neither compound is capable of having geometric isomers). Provide the structures of these compounds in the boxes below. No IUPAC names are necessary. F
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.
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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