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Everything about Hofmann Bromamide Reaction

ORGANIC CHEMISTRY IS EASY
Instructor:
Bharti Gupta
1 student enrolled
This series of videos give the students a complete information about Hofmann bromamide Reaction. This reaction is one the most important reaction of organic chemistry because many important questions are directly asked in competitive exam.

In this course I am offering you details of Hofmann Bromamide reaction which is also called as Hofmann degradation Reaction. In this course I have taken everything related to this including 21 concept building question which gives all types of permutation and combination related to topic. Here I have given

1. General Concept of Hofmann Bromamide reaction

2. Mechanism

3. Factors affecting its reactivity

4. Stereochemistry involved in it

5. Intramolecular nature of reaction

6. Twenty one best Questions which explains everything about it.

Introduction

1
Introduction

Myself Bharti Gupta, your mentor and your coach for any problem related to Organic Chemistry. I am here for concept building, problem solving and all your queries regarding organic chemistry for those who are preparing for board or any competitive exam.

I have experience of 12 years of teaching for students preparing for various exams in India.

In this course I am offering you details of Hofmann Bromamide reaction. In this course I have taken everything related to this including 21 concept building question which gives all types of permutation and combination related to topic.

ORGANIC IS EASY

GOOD LUCK FOR YOUR FUTURE

2
Basic Information about Hofmann Bromamide Reaction

When a primary amide is treated with bromine in an aqueous or ethanolic solution of sodium hydroxide, degradation of amide takes place leading to the formation of primary amine. This reaction involving degradation of amide and is popularly known as Hoffmann bromamide degradation reaction.

3
Mechanism of Hofmann Bromamide Reaction

The reaction of bromine with sodium hydroxide forms sodium hypobromite which transforms the primary amide into an intermediate isocyanate. The formation of an intermediate nitrene is not possible because it implies also the formation of a hydroxamic acid as a byproduct, which has never been observed. The intermediate isocyanate is hydrolyzed to a primary amine, giving off carbon dioxide.

Here following steps occur in reaction

  1. Base abstracts an acidic N-H proton, yielding an anion.

  2. The anion reacts with bromine in an ╬▒-substitution reaction to give an N-bromoamide.

  3. Base abstraction of the remaining amide proton gives a bromoamide anion.

  4. The bromoamide anion rearranges as the R group attached to the carbonyl carbon migrates to nitrogen at the same time the bromide ion leaves, giving an isocyanate.

  5. The isocyanate adds water in a nucleophilic addition step to yield a carbamic acid (aka urethane).

  6. The carbamic acid spontaneously loses carbon dioxide yielding the primary amine as product.

4
Factors deciding Rate of Hofmann Bromamide Reaction
5
Stereochemistry of Hofmann Bromamide Reaction
6
Evidence of Intramolecular Nature of Hofmann Bromamide Reaction
7
Question which explain Which compound will not give Hofmann Bromamide Reaction
8
Question which explain about the major product of Hofmann Bromamide Reaction
9
Question which explain the different ways to write Hofmann Bromamide Reaction
10
Question which explain the number of moles Br2 & NaOH used in Hofmann Reaction
11
Question which explain the mixing of Molecular formula with Hofmann Reaction
12
Question which explain stereochemical change in Hofmann Bromamide Reaction
13
Question which explain change in product when alcohol is in Hofmann Reaction
14
Question which explain intramolecular reaction of Hofmann Bromamide
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Question which explain formation of cycle in Hofmann Bromamide Reaction
16
Question which explain position of attack in Hofmann Bromamide Reaction
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Question which explain relationship in Hofmann Bromamide Reaction
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Question which explain intermediate formation in Hofmann Bromamide Reaction
19
Question which explain mixing of reaction with Hofmann Bromamide Reaction
20
Question which explain mixing of reduction in Hofmann Bromamide Reaction
21
Question which explain mixing of oxidation in Hofmann Bromamide Reaction
22
Question which explain lactic formation in Hofmann Bromamide Reaction
23
Question which explain formation of another amide in Hofmann Bromamide Reaction
24
Question which explain incorrect product in Hofmann Bromamide Reaction
25
Question which explain Deuterium exchange in Hofmann Bromamide Reaction
26
Question which explain Hofmann Bromamide Reaction in cyclic compound
27
Question which explain Hofmann Bromamide Reaction in aromatic compound
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