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Acetamide is treated separately with the...

Acetamide is treated separately with the following reagents. Which one of these would give methylamine ?

A

`PCl_(5)`

B

`Br_(2) and NaOH`

C

`P_(4)O_(10)`

D

`LiAlH_(4)`

Text Solution

AI Generated Solution

The correct Answer is:
To determine which reagent will convert acetamide (CH3CO-NH2) to methylamine (CH3-NH2), we can analyze the reactions that acetamide undergoes with different reagents. ### Step-by-Step Solution: 1. **Identify the Structure of Acetamide**: - Acetamide has the structure CH3CO-NH2. It contains a carbonyl group (C=O) and an amine group (NH2). 2. **Understand the Desired Product**: - Methylamine has the structure CH3-NH2. This indicates that we need to remove the carbonyl group (C=O) and convert the acetamide into a primary amine. 3. **Recall the Hofmann Rearrangement**: - The Hofmann rearrangement is a reaction where primary amides are converted to primary amines with the loss of one carbon atom. This reaction typically involves the use of bromine (Br2) and a strong base (like NaOH). 4. **Apply the Hofmann Rearrangement to Acetamide**: - When acetamide (CH3CO-NH2) is treated with bromine in the presence of a strong base (NaOH), the carbonyl group is removed, and the product formed is methylamine (CH3-NH2). 5. **Evaluate the Given Reagents**: - The question provides several reagents. We need to identify which one can facilitate the Hofmann rearrangement: - **Option 1**: Bromine with a base (NaOH) - This will yield methylamine. - **Option 2**: Lithium Aluminium Hydride (LiAlH4) - This is a reducing agent that would convert acetamide to ethylamine (CH3CH2-NH2), not methylamine. - **Option 3**: Phosphorus pentoxide (P4O10) - This is a dehydrating agent and would not yield methylamine. - **Option 4**: Phosphorus pentachloride (PCl5) - This would convert acetamide to an acyl chloride, not methylamine. 6. **Conclusion**: - The reagent that will convert acetamide to methylamine is bromine in the presence of a strong base (NaOH), as per the Hofmann rearrangement. ### Final Answer: The reagent that would give methylamine from acetamide is **Bromine (Br2) with a strong base (NaOH)**.
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