Nitromethane is subjected to treatment with chlorine in the presence of sodium hydroxide, the main product is:

Options

A. Monochloronitromethane
B. Trichloromethane
C. Chloropicrin
D. None of the above

Explanation

To solve the question about the reaction of nitromethane with chlorine in the presence of sodium hydroxide, we will follow these steps:

### Step 1: Identify the Reactants
The reactants in this reaction are nitromethane (CH3NO2), chlorine (Cl2), and sodium hydroxide (NaOH).

### Step 2: Understand the Reaction Conditions
Sodium hydroxide is a strong base and will deprotonate the hydrogen atom attached to the carbon adjacent to the nitro group in nitromethane. This results in the formation of a more reactive intermediate.

### Step 3: Deprotonation of Nitromethane
When nitromethane (CH3NO2) reacts with NaOH, one of the hydrogen atoms on the carbon is removed, forming a carbanion:
\[ \text{CH}_3\text{NO}_2 + \text{NaOH} \rightarrow \text{CH}_2\text{NO}_2^{-} + \text{Na}^+ + \text{H}_2\text{O} \]

### Step 4: Chlorination of the Intermediate
The carbanion (CH2NO2^-) can now react with chlorine (Cl2). The nucleophilic carbanion attacks the chlorine molecule, leading to the formation of chlorinated nitromethane:
\[ \text{CH}_2\text{NO}_2^{-} + \text{Cl}_2 \rightarrow \text{CH}_2\text{Cl}\text{NO}_2 + \text{Cl}^- \]

### Step 5: Further Chlorination
The chlorinated product (CH2ClNO2) can undergo further deprotonation by NaOH, leading to another carbanion:
\[ \text{CH}_2\text{Cl}\text{NO}_2 + \text{NaOH} \rightarrow \text{CHCl}\text{NO}_2^{-} + \text{Na}^+ + \text{H}_2\text{O} \]

This carbanion can react with Cl2 again:
\[ \text{CHCl}\text{NO}_2^{-} + \text{Cl}_2 \rightarrow \text{CCl}_2\text{NO}_2 + \text{Cl}^- \]

### Step 6: Final Chlorination
The product (CCl2NO2) can undergo another deprotonation and chlorination:
\[ \text{CCl}_2\text{NO}_2 + \text{NaOH} \rightarrow \text{CCl}_3\text{NO}_2^{-} + \text{Na}^+ + \text{H}_2\text{O} \]
\[ \text{CCl}_3\text{NO}_2^{-} + \text{Cl}_2 \rightarrow \text{CCl}_3\text{NO}_2 + \text{Cl}^- \]

### Step 7: Identify the Final Product
The final product formed is trichloronitromethane, which is commonly known as chloropicrin (CCl3NO2).

### Conclusion
The main product formed from the reaction of nitromethane with chlorine in the presence of sodium hydroxide is **chloropicrin (CCl3NO2)**, which corresponds to option C.

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