8.32(a)The problem states that the reaction type is nucleophilic substitution. Sodium acetylideis therefore the nucleophile and must be treated with an alkyl halide to give the desiredproduct.(b)The acidity data given in the problem for acetylene tell us that HC>CH is a very weak acid(Ka5 10226), so that sodium acetylide must be a very strong base—stronger than hydroxideion.Eliminationby the E2 mechanism rather than SN2 substitution is therefore expected to bethe principal (probably the exclusive) reaction observed with secondary and tertiary alkylhalides. The substitution reaction will work well with primary alkyl halides but will likely failfor secondary and tertiary ones. Alkynes such as (CH3)2CHC>CH and (CH3)3CC>CHcould not be prepared by this method.8.33The compound that reacts with trans-4-tert-butylcyclohexanol is a sulfonyl chloride and convertsthe alcohol to the corresponding sulfonate.
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