58E - Organic Chemistry (Mcmurry)

Question

How would you synthesize the following compounds from cyclohexanone?

More than one step may be required.

Step-by-Step Solution

Answer

a) 

b)

c)

d)

e)

f) 

Step 1: Preparation of compound (a)

The process for the formation of compound (a), that is, methylenecyclohexane from cyclohexanone is as follows,

Step 2: Preparation of compound (b)

The process for the formation of compound (b) that is, bromomethyl cyclohexane from cyclohexanone, is as follows,

Step 3: Preparation of compound (c)

The process for the formation of compound (c), that is, 2-benzylcyclohexan-1-one from cyclohexanone is as follows,

Step 4: Preparation of compound (d)

The process for the formation of compound (d), that is, 3-cyclohexylpropanoic acid from cyclohexanone is as follows,

Step 5: Preparation of compound (e)

The process for the formation of compound (e), that is, cyclohex-1-ene-1-carboxylic acid from cyclohexanone is as follows,

Step 6: Preparation of compound (f)

The process for formation of compound (f), that is, cyclohex-2-en-1-one from cyclohexanone is as follows,