Dolbier HW Solutions 339

Dolbier HW Solutions 339 - 433 ALDEHYDES AND KETONES:...

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( c ) 17.13 ( b ) Here we see an example of the Wittig reaction applied to diene synthesis by use of an ylide containing a carbon carbon double bond. ( c ) Methylene transfer from methylenetriphenylphosphorane is one of the most commonly used Wittig reactions. 17.14 A second resonance structure can be written for a phosphorus ylide with a double bond between phosphorus and carbon. As a third-row element, phosphorus can have more than 8 electrons in its valence shell. 17.15 ( b ) Two Wittig reaction routes lead to 1-pentene. One is represented retrosynthetically by the disconnection The other route is 1-Pentene CH 3 CH 2 CH 2 CH CH 2 1 Formaldehyde O HCH Butylidenetriphenylphosphorane CH 3 CH 2 CH 2 CH 1 2 P(C 6 H 5 ) 3 1 1-Pentene CH 3 CH 2 CH 2 CH CH 2 CH 3 CH 2 CH 2 CH O Butanal Methylenetriphenyl- phosphorane 1 2 CH
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