Predict the products of the following reactions.
(f)

Verified step by step guidance

Step 1: Identify the functional groups in the reactant. The molecule contains an amine group (-NH2) and a nitrile group (-CN). The reaction involves hydrolysis under acidic conditions (H3O+ and heat).

Step 2: Understand the mechanism of nitrile hydrolysis. Under acidic conditions, the nitrile group (-CN) is converted into a carboxylic acid (-COOH) through intermediate formation of an imidic acid and subsequent tautomerization.

Step 3: Consider the stability of the amine group (-NH2) under acidic conditions. The amine group is protonated to form an ammonium ion (-NH3+), but it remains intact during the reaction.

Step 4: Predict the product structure. The nitrile group (-CN) is replaced by a carboxylic acid group (-COOH), while the amine group (-NH2) remains attached to the same carbon atom.

Step 5: Verify the stereochemistry and connectivity of the product. The original carbon skeleton is preserved, and the final product is an amino acid with both an amine group (-NH2) and a carboxylic acid group (-COOH) on the same carbon atom.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, leading to the formation of a new bond. In this case, the amino group (NH2) acts as a nucleophile, attacking the carbon atom of the nitrile (CN) group, which is electrophilic due to the triple bond's polarity.

Hydrolysis of Nitriles

Hydrolysis of nitriles involves the reaction of a nitrile with water, often in the presence of an acid or base, to convert it into a carboxylic acid. In this reaction, the nitrile group is transformed into a carboxylic acid through the addition of water, facilitated by the acidic conditions provided by H3O+.

Acid-Base Catalysis

Acid-base catalysis refers to the acceleration of a chemical reaction by the presence of an acid or base. In this scenario, H3O+ serves as an acid that protonates the nitrile, making it more susceptible to nucleophilic attack by the amino group, thus enhancing the reaction rate and product formation.

Predict the products of the following reactions. (f)