Draw the structures of the organic products in each reaction of thefollowing two-step synthesis. (Hint: The nucleophilic amine attacks the electrophilic carbonyl carbon,and the resulting intermediate undergoes a proton shift anddehydration. Recall what is eliminated in a dehydration process.The second step is a reduction reaction; the reducing agent isNaBH3CN (or H2, metal catalyst). The aromatic ring is unaffected bythese reagents. Look at the product of the first reaction andconsider what can be easily reduced.)


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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).


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.

You are watching: Draw the organic product of the two-step synthesis 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:

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The reduction of the Schiff base is given below:



The structure of the organic product of the given reaction is


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