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Show me the mechanism of this reaction using only 1 bromination.   *R listed is NHCOCH3.

Show me the mechanism of this reaction using only 1 bromination.   *R listed is NHCOCH3.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Show me the mechanism of this reaction using only 1 bromination.  

*R listed is NHCOCH3. 

 

### Aromatic Bromination Reaction The image depicts a chemical reaction involving the bromination of an aromatic compound. Below is a detailed breakdown of the reaction illustrated: #### Reactant: - **Structure:** A benzene ring (aromatic compound) with a generic substituent denoted as "R" attached to one of its carbon atoms. - **Notation:** The benzene ring is represented with alternating single and double bonds. #### Reagent: - **Pyridinium Tribromide:** The reagent used for bromination, often utilized as a safer alternative to Br₂ for introducing bromine into organic compounds. - **Solvent:** Acetic acid (CH₃COOH) serves as the solvent for the reaction. #### Product: - **Structure:** A brominated benzene ring with the same substituent "R" and a new bromine atom (Br) attached to one of the carbon atoms in the ring. - **Notation:** The newly introduced Br is shown on the benzene ring. ### Description: In this reaction, pyridinium tribromide in an acetic acid solvent acts to brominate the aromatic ring. The bromine selectively adds to one position on the ring, influenced by the position of "R," an existing substituent. This is an example of electrophilic aromatic substitution. This diagram captures the transformation of the benzene ring as it undergoes substitution, illustrating the fundamental principles of organic aromatic reactions.
Transcribed Image Text:### Aromatic Bromination Reaction The image depicts a chemical reaction involving the bromination of an aromatic compound. Below is a detailed breakdown of the reaction illustrated: #### Reactant: - **Structure:** A benzene ring (aromatic compound) with a generic substituent denoted as "R" attached to one of its carbon atoms. - **Notation:** The benzene ring is represented with alternating single and double bonds. #### Reagent: - **Pyridinium Tribromide:** The reagent used for bromination, often utilized as a safer alternative to Br₂ for introducing bromine into organic compounds. - **Solvent:** Acetic acid (CH₃COOH) serves as the solvent for the reaction. #### Product: - **Structure:** A brominated benzene ring with the same substituent "R" and a new bromine atom (Br) attached to one of the carbon atoms in the ring. - **Notation:** The newly introduced Br is shown on the benzene ring. ### Description: In this reaction, pyridinium tribromide in an acetic acid solvent acts to brominate the aromatic ring. The bromine selectively adds to one position on the ring, influenced by the position of "R," an existing substituent. This is an example of electrophilic aromatic substitution. This diagram captures the transformation of the benzene ring as it undergoes substitution, illustrating the fundamental principles of organic aromatic reactions.
Expert Solution
Step 1: Role of Reagent

Pyridinium tribromide is the source of Br2 which is attacked by the ring as the lone pair of N gets delocaised .

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