rovide an arrow pushing mechanism for the following reaction OH CH₂ HBr CH3CN (solvent) H₂C

Chemistry
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Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Mechanism of Reaction:**

The task is to provide an arrow-pushing mechanism for the following reaction, which involves the conversion of a primary alcohol to a cyclic amide using hydrogen bromide (HBr) in acetonitrile (CH₃CN) as the solvent.

**Structure of Reactants:**

- **Starting Material:**
  - A structure with a benzene ring (phenyl group) attached to a long carbon chain.
  - This chain includes an alcohol group (OH) and an amide group (NHC=O).

**Reagents:**

- **HBr (Hydrogen Bromide):** 
  - Acts as the source of bromine ion for substitution.
  
- **CH₃CN (Acetonitrile):** 
  - Used as a polar aprotic solvent facilitating the reaction.

**Structure of Product:**

- A cyclic amide (lactam) with a phenyl group and a five-membered ring.
- Shows transformation from a linear structure to a cyclic one through intramolecular reaction.

**Mechanism Overview:**

1. **Protonation of Alcohol:**
   - The OH group is protonated by HBr, converting it into a better leaving group (water).

2. **Formation of Bromide Ion:**
   - The bromide ion acts as a nucleophile and attacks the electrophilic carbon, facilitating the departure of the water group.

3. **Intramolecular Cyclization:**
   - Nucleophilic attack by the amide nitrogen on the electrophilic carbon previously bonded with alcohol occurs, forming a new C-N bond and closing the ring.

This reaction exemplifies a nucleophilic substitution mechanism followed by intramolecular cyclization, resulting in the formation of a cyclic amide.
Transcribed Image Text:**Mechanism of Reaction:** The task is to provide an arrow-pushing mechanism for the following reaction, which involves the conversion of a primary alcohol to a cyclic amide using hydrogen bromide (HBr) in acetonitrile (CH₃CN) as the solvent. **Structure of Reactants:** - **Starting Material:** - A structure with a benzene ring (phenyl group) attached to a long carbon chain. - This chain includes an alcohol group (OH) and an amide group (NHC=O). **Reagents:** - **HBr (Hydrogen Bromide):** - Acts as the source of bromine ion for substitution. - **CH₃CN (Acetonitrile):** - Used as a polar aprotic solvent facilitating the reaction. **Structure of Product:** - A cyclic amide (lactam) with a phenyl group and a five-membered ring. - Shows transformation from a linear structure to a cyclic one through intramolecular reaction. **Mechanism Overview:** 1. **Protonation of Alcohol:** - The OH group is protonated by HBr, converting it into a better leaving group (water). 2. **Formation of Bromide Ion:** - The bromide ion acts as a nucleophile and attacks the electrophilic carbon, facilitating the departure of the water group. 3. **Intramolecular Cyclization:** - Nucleophilic attack by the amide nitrogen on the electrophilic carbon previously bonded with alcohol occurs, forming a new C-N bond and closing the ring. This reaction exemplifies a nucleophilic substitution mechanism followed by intramolecular cyclization, resulting in the formation of a cyclic amide.
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