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Unformatted text preview: 14-10 c ontinued (b) (1) (2) o H g(OAch .. (c) (1)
(2) A lkoxymercuration i s not practical here ; the product does not h ave Markovnikov orientation . (d) (1)
(2) (yoH 6 -- Na C H31 .. (y O OCH 1 H g(OAch C H30 H
.. NaB H4
.. CH 1 (e) (1) Hg(OAch
------� .. � NaBH4
OH Na (2) Wi lliamson ether synthesis would give a poor yield of product as the hal ide i s on a 2° c arbon. (f) (1) O H
-- ==< o- H g(OAch .. K�
.. OH (2) Wi l liamson ether synthesis is n o t feasible here. SN2 does n o t work on either a benzene or a 3 ° halide. ( }-o+
3 02 14-11 An i mportant pri nciple of synthesis is to avoid mixtures of i somers wherever possible; minimizing separations increases recovery of products. Bimolecular d ehydration is a r andom process . Heating a m ixture of ethanol and methanol w ith acid wi l l produce all possible combinations: dimethyl ether, ethyl methyl ether, and diethy l ether. Thi s mixture would be troublesome to separate. ...
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- Spring '10