Q16P - Organic Chemistry (Mcmurry)

Question

How would you prepare 1-phenyl-2-butanone, C₆H₅CH₂COCH₂CH₃, from benzyl 

bromide, C₆H₅CH₂Br? More than one step is required?

Step-by-Step Solution

Answer

The preparation of 1-phenyl-2-butanone, C₆H₅CH₂COCH₂CH₃, from benzyl bromide, 

C₆H₅CH₂Br can be explained.

Step 1: Formation of bonds

The metal Mg reacts with the benzyl bromide for the formation of benzyl magnesium 

bromide. There is a breaking of C-Br bond and formation of C-Mg and Mg-Br bonds.

Step 2: 1-phenyl-2-butanone formation

The reaction of propanol with benzylmagnesium bromide which follows the acidification 

for the formation of 1-phenylbutan-2-ol. The double bond with C and O of propanol c-

can be converted to the single bond of C-O and O-H and also the formation of O-H and 

C-C bonds. The oxidation of secondary alcohol to ketone.