Dolbier HW Solutions 231

Dolbier HW Solutions 231 - 225 ALKYNES Treatment of...

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Treatment of compound A with sodium amide converts it to compound B. Compound B on ozonol- ysis gives a diacid that retains all the carbon atoms of B. Compound B must therefore be a cyclic alkyne, formed by an intramolecular alkylation. Compound B is cyclotetradecyne. Hydrogenation of compound B over Lindlar palladium yields cis -cyclotetradecene (compound C). Hydrogenation over platinum gives cyclotetradecane (compound D). Sodium ammonia reduction of compound B yields trans -cyclotetradecene. The cis and trans isomers of cyclotetradecene are both converted to O ? CH(CH 2 ) 12 CH ? O on ozonolysis, whereas cyclotetradecane does not react with ozone.
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