Aldehydes & Ketones: Multi-Step Synthesis
Suggest a synthetic scheme for the conversion shown on the left using the starting material indicated. Work each problem backwards, and draw the structures of the intermediate required for the conversion, and the reaction conditions necessary for each step.Click the mouse on the buttons to view the synthetic logic, the structure of the intermediate and the solution to the problem.
Click the mouse on the molecule to reset this frame.
Working backwards, this molecule is a aryl ketone and the phenyl group has been added to the carbon skeleton of our starting material (an aldehyde). We can make aryl ketones by oxidation of the corresponding alcohol, which could be formed from the starting aldehyde by the addition of phenylmagnesium bromide (a Grignard reaction). First, draw the structure of the required alcohol.
Working backwards, this molecule is a aryl ketone and the phenyl group has been added to the carbon skeleton of our starting material (an aldehyde). We can make aryl ketones by oxidation of the corresponding alcohol, which could be formed from the starting aldehyde by the addition of phenylmagnesium bromide (a Grignard reaction). Next, draw the structure of the required Grignard reagent.
Acetaldehyde (ethanal) is reacted with phenylmagnesium bromide to give 1-phenylethanol. Simple oxidation of this alcohol gives the desired product, acetophenone (phenylethanone).