Question

An alkane (A) with the formula CgH14 reacts with chlorine to yield three compounds with the formula CgH13Cl: 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 magnesium in dry ether followed by aqueous acid gives a compound (G) that is isomeric with A. Propose structures for A-G. 13. Compound A (C4Hg) reacts with hydrogen and a platinum catalyst to yield butane. Compound A reacts with Br2 in CCl4 and aqueous KMnO4 The IR spectrum of A does not have an absorption in the 2200-2300-cm region. On treatment with hydrogen and Ni2B (P-2 catalyst), A is converted to B (C4Hg). When B is treated with OsO4 and then with NaHS03. B is converted to C (C4H1002). Compound C cannot be resolved. Provide structures for A-C Dehalogenation of meso-2,3-dibromobutane occurs when it is treated with potassium iodide in ethanol. The prod- uct is trans-2-butene. Similar dehalogenation of either of the enantiomeric forms of 2,3-dibromobutane produces cis-2-butene. Give a mechanistic explanation of these results. 14. 15,

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