Dolbier HW Solutions 365

Dolbier HW Solutions 365 - 459 ALDEHYDES AND KETONES...

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( d ) Remember that terminal acetylenes can serve as sources of methyl ketones by hydration. This gives us a clue as to how to proceed, since the acetylenic ketone may be prepared from the starting acetylenic alcohol. The f rst synthetic step is oxidation of the primary alcohol to the aldehyde and construction of the carbon skeleton by a Grignard reaction. Oxidation of the secondary alcohol to a ketone and hydration of the terminal triple bond com- plete the synthesis. ( e ) The desired product is a benzylic ether. To prepare it, the aldehyde must f rst be reduced to the corresponding primary alcohol. Sodium borohydride was used in the preparation described in the literature, but lithium aluminum hydride or catalytic hydrogenation would also be possi- ble. Once the alcohol is prepared, it can be converted to its alkoxide ion and this alkoxide ion treated with methyl iodide. Alternatively, the alcohol could be treated with hydrogen bromide or with phosphorus tribro-
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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