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SCAN0006 - H3CHC——-““"CHCH3 mixture of cis(32...

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Unformatted text preview: H3CHC——-““"CHCH3 mixture of cis (32%) and trans—l-butene (56%) Carbocations can.“ _ \ m6 v A x e ’- - react w1th nucleophlles Wlfi (fils E, 4 lose a proton from the B-carbun to form an alkene rearrange (less stable to more Stable) “we 5.14 Dehydrohalogenation of Alkyl Halides LE2) is a useful method for the preparation of alkenes NaOCH___—E__+CH3 ethanol 55 0c , t l 00% likewise, NaOCH3 in methanol, or KOH in ethanol Conditions: 3° and 2° NaOCHa, CH30H MW, \dlSfiS 1° KOC(CH3)3, (CH3)3COH‘ m8) @383 When the alkyl halide is primary, potassium tert-butoxide in dimethyl sulfoxide is the base/solvent system that is normally used. KOC(CH3)3 H CH CH ‘ ‘ ——-—-———> CH CH CH=CIL C 3( 2)” 2CH2C1 dimethylsulfoxidc 3( 2)” ‘ (DMSO) @ follow.rule more highly substituted double bond predominates ...
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