Q77E
Question
6-Methyl-5-hepten-2-one is a constituent of lemongrass oil. How could you synthesize this substance from methyl 4-oxopentanoate?
Methyl 4-oxopentanoate
Step-by-Step Solution
VerifiedThe synthesis of the given reaction involves protecting the ketone, converting the ester into an aldehyde, using Wittig reaction to introduce a substituted double bond and the last step is deprotecting the ketone to synthesize the given product.
The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes. The geometry of the resulting alkene depend upon the reactivity of the ylide. Ylides can be synthesized from an alky halide and trialkyl phosphine.
Wittig reaction
The synthesis of the given reaction involves following sequence:
1. Protecting the ketone
2. Converting the ester into an aldehyde
3. Using Wittig reaction to introduced a substituted double bond.
4. The last step is deprotecting the ketone
Synthesis of 6-methyl-5-hepten-2-one