Q25-E - Organic Chemistry (Mcmurry)

Question

Predict the product(s) and provide the mechanism for each two-step

process below.

Step-by-Step Solution

Answer

a.

b. 

c.

d.

Step 1: The Williamson Ether Synthesis

It’s the reaction for the formation of ether from the alcohol by formation of alkoxide ion in presence of a strong base like NaH and followed by reaction with an alkyl halide to form ether.

Step 2: Reaction of compound A

As the reaction the step is followed as:

1. Phenol reacts with the base NaH the proton of the hydroxyl group is the abstracted formation of alkoxide ion that occur
2.  further reaction with alkyl halide form ether as shown:

                                               Formation of ester

Step 3: Reaction of compound B

The two steps are followed as:

1. Propanol reacts with the base NaH the proton of the hydroxyl group is the abstracted formation of alkoxide ion occurs.
2. Further reaction with alkyl halide that is propyl bromide propyl attach with the oxygen ion and ether formation occur as shown below:

                                                 Formation of Ester

Step 4: Reaction of compound C

The two steps process is given as:

1. Cyclopentanol reacts with the base NaH the proton of the hydroxyl group is the abstracted formation of alkoxide ion occurs.
2.  Further reaction with tosylate that is methoxy tosylate attach with the oxygen ion and ether formation occur by the removal of tosylate ion as shown below:

Step 5: Reaction of compound D

The two steps process are:

1. 3-methyl pentan-3-ol react with the base NaH the proton of the hydroxyl group is the abstracted formation of alkoxide ion occurs.
2.  Further reaction with alkyl halide that is methyl bromide attach with the oxygen ion and ether formation occurs by the removal of bromide ion as shown below:

                                                 Formation of ester