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Dolbier HW Solutions 654

Dolbier HW Solutions 654 - 748 LIPIDS A Wittig reaction...

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A Wittig reaction converts the ketone to sabinene. 26.26 The f rst step is a 1,4 addition of hydrogen bromide to the conjugated diene system of isoprene. This is followed by Markovnikov addition of hydrogen bromide to the remaining double bond. 26.27 A reasonable mechanism is protonation of the isolated carbon carbon double bond, followed by cyclization. H O H OSO 2 OH 2 H 1 b -Ionone O a -Ionone O O 1 O 1 CH 3 CCH 2 CH 2 Br CH 3 Br 2 1 CH
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