Dolbier HW Solutions 227

Dolbier HW Solutions 227 - 221 ALKYNES j O Hydrogenation of...

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( j ) Hydrogenation of the triple bond over the Lindlar catalyst converts the compound to a cis alkene. 9.31 Ketones such as 2-heptanone may be readily prepared by hydration of terminal alkynes. Thus, if we had 1-heptyne, it could be converted to 2-heptanone. Acetylene, as we have seen in earlier problems, can be converted to 1-heptyne by alkylation. 9.32 Apply the technique of reasoning backward to gain a clue to how to attack this synthesis problem. A reasonable f nal step is the formation of the Z double bond by hydrogenation of an alkyne over Lindlar palladium. The necessary alkyne 9-tricosyne can be prepared by a double alkylation of acetylene. It does not matter which alkyl group is introduced f rst. The alkyl halides are prepared from the corresponding alcohols. CH 3 (CH 2 ) 12 OH 1-Tridecanol CH 3 (CH 2 ) 12
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