Fill in the missing reagents and intermediates in the synthesis of Lidocaine. Provide a detailed arrow pushing mechanism for the formation of Intermediate B. alo NO A NaOAc, ACOH C NH O

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**Title: Synthesis of Lidocaine: Mechanism and Reagents**

**Introduction:**
In this educational module, we will explore the synthesis of Lidocaine, a commonly used local anesthetic, by examining the reaction pathway and the mechanisms involved in its formation.

**Reaction Pathway:**

The synthesis involves multiple steps with different reagents and intermediates.

1. **Starting Material:**
   - The process begins with a nitrobenzene derivative with a nitro group (NO₂) on the benzene ring.

2. **Step A: Reduction**
   - Reagent: This step requires a reducing agent to convert the nitro group (NO₂) to an amine group (NH₂).
   - Product: An aniline derivative with an amine group on the benzene ring.

3. **Step B: Acylation**
   - Reagents: The aniline reacts with an acid chloride (ClCOCH₂Cl) in the presence of sodium acetate (NaOAc) and acetic acid (AcOH).
   - Product: Intermediate B is formed, which is an amide derivative, involving the attachment of the acyl group to the nitrogen of the amine.

4. **Step C: Alkylation**
   - Intermediate B undergoes further transformation with additional reagents (not specified here) to form Lidocaine.
   - Product: Lidocaine, featuring an amide linkage and a tertiary amino group in its structure.

**Mechanism Details:**

- **Reduction:** The conversion of the nitro group to an amine involves typical reduction reactions, often using reagents like iron and hydrochloric acid, reducing agents like tin and hydrochloric acid, or catalytic hydrogenation.

- **Acylation:** The amine reacts with an acid chloride in a nucleophilic acyl substitution, where the amine nitrogen attacks the carbonyl carbon, leading to the formation of the amide linkage after expelling the chloride ion.

**Conclusion:**

Understanding this multi-step synthetic pathway provides a solid foundation in organic synthesis techniques, particularly in forming complex molecules like Lidocaine. The reaction highlights the importance of choosing appropriate reagents and conditions to achieve desired transformations efficiently.
Transcribed Image Text:**Title: Synthesis of Lidocaine: Mechanism and Reagents** **Introduction:** In this educational module, we will explore the synthesis of Lidocaine, a commonly used local anesthetic, by examining the reaction pathway and the mechanisms involved in its formation. **Reaction Pathway:** The synthesis involves multiple steps with different reagents and intermediates. 1. **Starting Material:** - The process begins with a nitrobenzene derivative with a nitro group (NO₂) on the benzene ring. 2. **Step A: Reduction** - Reagent: This step requires a reducing agent to convert the nitro group (NO₂) to an amine group (NH₂). - Product: An aniline derivative with an amine group on the benzene ring. 3. **Step B: Acylation** - Reagents: The aniline reacts with an acid chloride (ClCOCH₂Cl) in the presence of sodium acetate (NaOAc) and acetic acid (AcOH). - Product: Intermediate B is formed, which is an amide derivative, involving the attachment of the acyl group to the nitrogen of the amine. 4. **Step C: Alkylation** - Intermediate B undergoes further transformation with additional reagents (not specified here) to form Lidocaine. - Product: Lidocaine, featuring an amide linkage and a tertiary amino group in its structure. **Mechanism Details:** - **Reduction:** The conversion of the nitro group to an amine involves typical reduction reactions, often using reagents like iron and hydrochloric acid, reducing agents like tin and hydrochloric acid, or catalytic hydrogenation. - **Acylation:** The amine reacts with an acid chloride in a nucleophilic acyl substitution, where the amine nitrogen attacks the carbonyl carbon, leading to the formation of the amide linkage after expelling the chloride ion. **Conclusion:** Understanding this multi-step synthetic pathway provides a solid foundation in organic synthesis techniques, particularly in forming complex molecules like Lidocaine. The reaction highlights the importance of choosing appropriate reagents and conditions to achieve desired transformations efficiently.
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