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  1. Dienes, Conjugation and Aromatic Compounds
  2. Reactions with Benzene
  3. Deuterium Substitution of Benzene
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1,2-Dienes
Conjugated Systems
Diels-Alder Reaction
Aromatic Compounds
Reactions with Benzene
Birch Reduction of Benzene
Hydrogenation of Benzene
Diels-Alder with Aromatic Molecules
Deuterium Substitution of Benzene
Sulfonation of Benzene
Nitration of Benzene
Halogenation of Benzene
Friedel-Crafts Alkylation
Friedel-Crafts Alkylation Example
Friedel-Crafts Acylation
Formation of Benzenediazonium Chloride
Reactions with Benzenediazonium Chloride
Electrophilic Substitution of Pyrrole and Pyridine
Ortho, Meta and Para Substitution
Ortho-Para Substitution Example
Meta Substitution Example
Inductive Effects in Electrophilic Substitution
Nucleophilic Addition of Benzene
Nucleophilic Addition to Benzene Example
Synthesis Reactions with Benzene (1)
Synthesis Reactions with Benzene (2)

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Deuterium Substitution of Benzene

Content Provider AK Lectures
Description Benzene molecules do not undergo the common electrophilic addition reaction because such reactions would cause the molecule to lose its aromaticity. However, substitution reactions of benzene do take place because these reactions, although break aromaticity momentarily, actually end up recreating its aromatic character in the final step. For example, if we mix benzene with a very strong and concentrated acid (say 90%) that is labeled with deuterium, all the hydrogen atoms on the benzene will be eventually replaced with deuterium while the aromatic character of benzene will not be lost. In the first step of this reaction, the pi bond on benzene grabs a deuterium atom to form a resonance stabilized intermediate carbocation. In the second step, the conjugate base of the acid used grabs a hydrogen atom off of the same carbon to which the deuterium was attached to, thereby reforming the benzene ring.
Language English
Access Restriction Open
Subject Keyword Organic Chemistry carbocation character reaction form grabs electrophilic addition reaction molecule resonance
Content Type Video
Educational Role Teacher Student
Educational Use Self Learning Lecture Reading
Resource Type Video Lecture
Education Level Under Graduate
Subject Organic chemistry
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