Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter FRP, Problem 13P

An alkane (A) with the formula C 6 H 14 reacts with chlorine to yield three compounds with the formula C 6 H 13 C l ; B, C, and D. Of these only C and D undergo dehydrohalogenation with sodium ethoxide in ethanol to produce an alkene. Moreover C and D yield the same alkene E ( C 6 H 12 ) . Hydrogenation of E produces A. Treating E with HCl produces a compound (F) that is an isomer of B, C, and D. Treating F with magnesium in dry ether followed by aqueous acid gives a compound (G) that is isomeric with A. Propose structures for A-G.

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