Question

Draw the structures of the organic products in each reaction of the following two-step synthesis. (Hint: The nucleophilic amine attacks the electrophilic carbonyl carbon, and the resulting intermediate undergoes a proton shift and dehydration. Recall what is eliminated in a dehydration process. The second step is a reduction reaction; the reducing agent is NaBH3CN (or H2, metal catalyst). The aromatic ring is unaffected by these reagents. Look at the product of the first reaction and consider what can be easily reduced.)

Answer 1

Concepts and reason

Major types of organic reactions are addition, substitution, elimination, condensation, rearrangement, oxidation and reduction reactions.

A condensation reaction is a type of organic reaction where an electron-deficient carbon atom reacts with an electron-rich reactant (nucleophile) to form a large molecule and remove a small molecule.

In organic chemistry, a reduction reaction is a type of chemical reaction where a carbon atom gains bonds with less electronegative elements (hydrogen).

Fundamentals

The condensation reaction of carbonyl compounds and amines is where an electron-deficient carbon atom easily reacts with an electron-rich nucleophile to form a double bond. The carbon atom carries a partial positive charge and the oxygen atom carries a partial negative charge. These electronegative properties make the carbon atom an electrophilic center. The general reaction mechanism is given below.

A nucleophile attacks the electron-deficient carbonyl carbon and is followed by dehydration to form a Schiff base form product.

The carbon-nitrogen double bond undergoes a reduction reaction in the presence of a reducing agent. The reaction is as follows:

The reduction of the Schiff base is given below:

Ans:

The structure of the organic product of the given reaction is