7 P - Organic Chemistry (Mcmurry)

Question

Question: What reagent would you use to accomplish each of the following reactions?

(a) 

(b)

(c)

Step-by-Step Solution

Answer

(a)

 

(b) 

(c)

Step-by-Step Solution Step 1: Alcohols from carbonyl compounds

Alcohols from carbonyl compounds can be prepared by using different reagents like , . Secondary alcohols are prepared from ketones using a reducing agent, whereas aldehydes give primary alcohols on reduction.

Step 2: The reagent used in the reaction (a)

(a) The starting compound contains one ketone group and one ester group in the given reaction. The reagent used here is because it reduces ketones and aldehydes without interfering with other functional groups present in a compound. Thus, the ketone group is only reduced to the OH group, and the ester group remains the same.

Alcohol from a carbonyl compound

Step 3: The reagent used in the reaction (b)

(b) The starting compound contains both ketone and ester groups in the given reaction. The reagent used here is because it is the strongest reducing agent that reduces both ketones and esters. Thus, the ketone and ester groups are reduced to the OH group.

Alcohol from a carbonyl compound

Step 4: The reagent used in reaction (c)

(c) The starting compound contains a ketone group and double bonds in the given reaction. The reagent used here is because it reduces carbonyl-containing functional groups without reducing double bonds. Thus, only the ketone group reduces to OH, and the double bonds remain as it is.

 

Alcohol from a carbonyl compound