Reactions Yielding
Carboxylic Acids
Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below:

   

The reaction of an aromatic side-chain with neutral, hot MnO4- oxidizes the side-chain at the benzylic carbon to give the carboxylic acid. At least one benzylic hydrogen is required for this reaction to occur.

Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below (show stereochemistry):

   

 

Again, the reaction of an aromatic side-chain with neutral, hot MnO4- oxidizes the side-chain at the benzylic carbon to give the carboxylic acid. At least one benzylic hydrogen is required for this reaction to occur.

Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below:

   

 

And once again, the reaction of an aromatic side-chain with neutral, hot MnO4- oxidizes the side-chain at the benzylic carbon to give the carboxylic acid. At least one benzylic hydrogen is required for this reaction to occur.

Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below:

   

 

Oxidation of a primary alcohol with CrO3/H2SO4 completely oxidizes the alcohol to the carboxylic acid.

Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below:

   

 

Oxidation of a primary alcohol with Na2Cr2O7/CH3COOH completely oxidizes the alcohol to the carboxylic acid.

Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below:

   

 

Oxidation of an alkene with acidic MnO4- splits the alkene, oxidizing disubstituted carbons to ketones, monosubstituted carbons to carboxylic acids, and terminal alkene carbons to CO2.

Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below:

   

 

CrO3 in H2SO4 is a powerful oxidizing agent and will oxidize an aldehyde to the corresponding carboxylic acid.

Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below:

   

 

Oxidation of an aldehyde with Na2Cr2O7/CH3COOH converts the aldehyde into the carboxylic acid.

Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below:

   

 

In the Tollens test for aldehydes, the aldehyde is oxidized to the carboxylic acid and the silver oxide is reduced to form the characteristic "silver mirror".

Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below.

   

 

Hot acidic MnO4- will oxidize a ketone, splitting the carbon-oxygen bond and yielding a carboxylic acid (a diacid in this case).

Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below.

   

 

A nitrile will undergo acid hydrolysis (hot aqueous mineral acid) to give the corresponding carboxylic acid.

Using the drawing pallet on the right, draw the structure of the major organic product for the reaction shown below.

   

A Grignard reagent will add carbon dioxide to form a carboxylic acid.

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Author: Peter Ertl