A complete, detailed mechanism is to be drawn for the given reaction. Concept introduction: Alkyl amines with a β-hydrogen undergo an elimination reaction when treated with excess iodomethane followed by silver oxide and heating. Unlike most elimination reactions, this reaction gives the least substituted alkene , an anti-Zaitsev product. The reaction is called Hofmann elimination. The Amine functional group is alkylated to a quaternary ammonium ion, converting it into a bulky and good leaving group. If there are two hydrogens in β positions, then the one that gives the less substituted alkene is eliminated. This is because the leaving group is bulky, and the β-hydrogen on the less substituted carbon is in an anti-position in the most stable conformer. Formation of a more substituted alkene would generally require a less stable gauche conformer.

Question

Want to see the full answer?

Answer 1

Question

Chapter 10, Problem 10.63P

Interpretation Introduction

Interpretation:

A complete, detailed mechanism is to be drawn for the given reaction.

Concept introduction:

Alkyl amines with a β-hydrogen undergo an elimination reaction when treated with excess iodomethane followed by silver oxide and heating. Unlike most elimination reactions, this reaction gives the least substituted alkene, an anti-Zaitsev product. The reaction is called Hofmann elimination.

The Amine functional group is alkylated to a quaternary ammonium ion, converting it into a bulky and good leaving group. If there are two hydrogens in β positions, then the one that gives the less substituted alkene is eliminated. This is because the leaving group is bulky, and the β-hydrogen on the less substituted carbon is in an anti-position in the most stable conformer. Formation of a more substituted alkene would generally require a less stable gauche conformer.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

What is the differences between: Glyceride and phosphoglyceride Wax and Fat Soap and Fatty acid HDL and LDL cholesterol Phospho lipids and sphingosine What are the types of lipids? What are the main lipid components of membrane structures? How could lipids play important rules as signaling molecules and building units? The structure variety of lipids makes them to play significant rules in our body, conclude breifly on this statement.

What is the differences between DNA and RNA for the following: - structure - function - type What is the meaning of: - replication - transcription - translation show the base pair connection(hydrogen bond) in DNA and RNA

What is the IP for a amino acid- give an example what are the types of amino acids What are the structures of proteins The N-Terminal analysis by the Edman method shows saralasin contains sarcosine at the N-terminus. Partial hydrolysis of saralasin with dilute hydrochloric acid yields the following fragments: Try-Val-His Sar-Arg-Val His-Pro-Ala Val- Tyr- Val Arg-Val-Tyr What is the structure of saralasin?