top of page

Ketones from Carboxylic Acids

Link to video on ketones from carboxylic acids

Previous

Home

Next

Ketones from Carboxylic Acids

Ketones can be synthesized from carboxylic acids. To do this, the proton of the carboxylic proton must first be removed using a base. This can be done by using lithium hydroxide (LiOH) as the base. Any alkyl lithium compound could also work. This deprotonation forms a carboxylate ion. A nucleophilic, negatively charged alkyl group can attack the carbonyl of this carboxylate. The electrons go up onto the oxygen atom. This forms a species with two negatively charged oxygen atoms. Following protonation using acid and water, a geminal diol is formed. Geminal diols like this are unstable, and easily dehydrate forming a carbonyl. In this case, the dehydration forms a ketone.

Reaction of carboxylic acid with LiOH and RLi to make ketone

6. Fill in the blank boxes.

a)

Ketone from carboxylic acid problem

b)

Ketone from carboxylic acid problem

Answers

6.

a)

Ketone from carboxylic acid problem answer

b)

Ketone from carboxylic acid problem answer

Previous

Home

Next

bottom of page