Q17-57E - Organic Chemistry (Mcmurry)

Question

How would you carry out the following transformations?

(a)

(b)

(c)

Step-by-Step Solution

Answer

The answer is 

(a)

(b)

(c)

Step 1: Reduction

The reduction of carboxylic acids leads to the formation of alcohols, and various reagents are used for this process. The acids can be selectively reduced in other functional groups using specific reagents.

Step 2: Subpart (a)

The double bond is selectively reduced to a single bond in the presence of carboxylic acids using a palladium catalyst and hydrogen

                                                         Reaction (a)

Step 3: Subpart (b)

The acid is converted into alcohol using Lithium Aluminium hydride followed by hydrolysis.

                                                        Reaction (b)

Step 4: Subpart (c)

The carboxylic acid is converted to thiol using the tribromo phosphide and alkyl thiane in the presence of the base.

                                                     Reaction (c)