Which of the following does/do produce a white precipitate of `AgCl` on warming with alcoholic silver nitrate?

Options

A. Allyl chloride
B. t-Butyl chloride
C. Benzyl chloride
D. Vinyl chloride

Answer

To determine which of the given compounds produce a white precipitate of AgCl when warmed with alcoholic silver nitrate (AgNO3), we need to analyze each compound's structure and reactivity with AgNO3 in the presence of alcohol.

### Step-by-Step Solution:

1. **Understanding the Reaction**:
- When alkyl halides react with alcoholic silver nitrate, they can undergo a nucleophilic substitution reaction. The chloride ion (Cl-) is replaced by an alcohol group (OH), resulting in the formation of an alcohol and the precipitation of silver chloride (AgCl).

2. **Analyzing Allyl Chloride**:
- Structure: Allyl chloride is CH2=CH-CH2Cl.
- Reaction: When allyl chloride reacts with alcoholic AgNO3, it forms allyl alcohol (CH2=CH-CH2OH) and AgCl.
- **Conclusion**: Allyl chloride produces a white precipitate of AgCl.

3. **Analyzing Butyl Chloride**:
- Structure: Butyl chloride can be primary (n-butyl), secondary, or tertiary. For tertiary butyl chloride (C(CH3)3Cl), we will consider it.
- Reaction: Tertiary butyl chloride reacts with alcoholic AgNO3 to form tert-butanol (C(CH3)3OH) and AgCl.
- **Conclusion**: Tertiary butyl chloride produces a white precipitate of AgCl.

4. **Analyzing Benzyl Chloride**:
- Structure: Benzyl chloride is C6H5-CH2Cl.
- Reaction: Benzyl chloride reacts with alcoholic AgNO3 to form benzyl alcohol (C6H5-CH2OH) and AgCl.
- **Conclusion**: Benzyl chloride produces a white precipitate of AgCl.

5. **Analyzing Vinyl Chloride**:
- Structure: Vinyl chloride is CH2=CHCl.
- Reaction: Vinyl chloride does not react with alcoholic AgNO3 due to the presence of a partial double bond character (PDC) in the C-Cl bond, which makes it stronger and less reactive.
- **Conclusion**: Vinyl chloride does not produce a white precipitate of AgCl.

### Final Answer:
- **Compounds that produce a white precipitate of AgCl**: Allyl chloride, Tertiary butyl chloride, and Benzyl chloride.
- **Compound that does not produce a white precipitate of AgCl**: Vinyl chloride.