Dolbier HW Solutions 205

Dolbier HW Solutions 205 - 199 NUCLEOPHILIC SUBSTITUTION...

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8.32 ( a ) The problem states that the reaction type is nucleophilic substitution. Sodium acetylide is therefore the nucleophile and must be treated with an alkyl halide to give the desired product. ( b ) The acidity data given in the problem for acetylene tell us that HC > CH is a very weak acid ( K a 5 10 2 26 ), so that sodium acetylide must be a very strong base stronger than hydroxide ion. Elimination by the E2 mechanism rather than S N 2 substitution is therefore expected to be the principal (probably the exclusive) reaction observed with secondary and tertiary alkyl halides. The substitution reaction will work well with primary alkyl halides but will likely fail for secondary and tertiary ones. Alkynes such as (CH 3 ) 2 CHC > CH and (CH 3 ) 3 CC > CH could not be prepared by this method. 8.33 The compound that reacts with trans -4- tert -butylcyclohexanol is a sulfonyl chloride and converts the alcohol to the corresponding sulfonate.
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