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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