Succinic anhydride yields the cyclic imide succinimide when heated with ammonium chloride at 200°C. Propose a mechanism for this reaction.

Question

Draw mechanisms for the acetylation of aniline, the bromination of acetanilide and the hydrolysis of 4-bromoacetanilide (REMEMBER: NBS generates bromine in solution) Reagents used: aniline, acetic acid, acetic anhydride to make acetanilide. Then acetanilide dissolved in acetic acid, NBS, aqHBr to make 4-bromoaxetanilinde. Then 4-bromoacetanilinde, EtOh, HCl and NaOH (to neutralise) to make 4-bromoaniline Please include drawings of the mechanisms as well as a written explanation as it helps me process exactly whats going on...

Answer 1

Question

Chapter 21.SE, Problem 39MP

Interpretation Introduction

Interpretation:

Succinic anhydride yields the cyclic imide succinimide when heated with ammonium chloride at 200°C. Propose a mechanism for this reaction.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Draw mechanisms for the acetylation of aniline, the bromination of acetanilide and the hydrolysis of 4-bromoacetanilide (REMEMBER: NBS generates bromine in solution) Reagents used: aniline, acetic acid, acetic anhydride to make acetanilide. Then acetanilide dissolved in acetic acid, NBS, aqHBr to make 4-bromoaxetanilinde. Then 4-bromoacetanilinde, EtOh, HCl and NaOH (to neutralise) to make 4-bromoaniline Please include drawings of the mechanisms as well as a written explanation as it helps me process exactly whats going on...

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.

The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.