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An alkane (A) with the formula C6H14 reacts with chlorine and light to form thre

ID: 836314 • Letter: A

Question

An alkane (A) with the formula C6H14 reacts with chlorine and light to form three compounds with the formula C6H13Cl: 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 (C6H12). 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 Zn and acetic acid (replaces Cl with H) gives an alkane (G) which is isomeric with A. Propose structures for compounds A-G and write all the reactions.

Explanation / Answer

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