A mechanism has to be proposed for the given acid-catalyzed hydrolysis reaction. Concept introduction: Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. If the reaction is carried out with the help of an acid it is said to be an acid catalyzed hydrolysis. Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products. Curved arrows show the bonds that are formed and the bonds that are broken in a reaction. Curved arrows used to understand a reaction mechanism. Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of chemical bond . Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.

Question

The mechanism for acidic hydrolysis of a nitrile resembles the basic hydrolysis, exceptthat the nitrile is first protonated, activating it toward attack by a weak nucleophile (water).Under acidic conditions, the proton transfer (tautomerism) involves protonation on nitrogen followed by deprotonation on oxygen. Propose a mechanism for the acid-catalyzedhydrolysis of benzonitrile to benzamide.

Answer 1

Question

Chapter 16, Problem 16.33P

Interpretation Introduction

Interpretation: A mechanism has to be proposed for the given acid-catalyzed hydrolysis reaction.

Concept introduction:

Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. If the reaction is carried out with the help of an acid it is said to be an acid catalyzed hydrolysis.

Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products.

Curved arrows show the bonds that are formed and the bonds that are broken in a reaction.

Curved arrows used to understand a reaction mechanism.

Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of chemical bond.

Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.

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