Which of the following organic compounds unable to give precipitation after reaction with silver nitrate `(AgNO_3)` ?

Options

A.
B. `(CH_3)_(3)C Cl`
C. `CH_3CH = CH- Cl`
D. `CH_2=CH-CH_2-Cl`

Answer

To determine which organic compound is unable to give precipitation after reacting with silver nitrate (AgNO₃), we need to analyze the stability of the carbocations formed when the carbon-chlorine (C-Cl) bond breaks in each compound. The precipitation occurs when the chlorine ion is released and reacts with silver ions to form silver chloride (AgCl), which is a precipitate.

### Step-by-Step Solution:

1. **Identify the Compounds**: We have the following compounds to analyze:
- A. CH₃CH₂Cl (Ethyl chloride)
- B. CH₃CCl₃ (1,1,1-Trichloroethane)
- C. CH₂=CHCl (Vinyl chloride)
- D. CH₃CCl₂H (1,1-Dichloroethane)

2. **Analyze Each Compound**:
- **Compound A (Ethyl chloride, CH₃CH₂Cl)**:
- When the C-Cl bond breaks, it forms a primary carbocation (CH₃CH₂⁺), which is relatively unstable but can still form. Thus, it can react with AgNO₃ and give a precipitate.

- **Compound B (1,1,1-Trichloroethane, CH₃CCl₃)**:
- When the C-Cl bond breaks, it forms a tertiary carbocation (CH₃C⁺), which is very stable due to the inductive effect of the three methyl groups. Therefore, it can easily react with AgNO₃ and give a precipitate.

- **Compound C (Vinyl chloride, CH₂=CHCl)**:
- When the C-Cl bond breaks, it forms a vinyl carbocation (CH₂=CH⁺), which is stabilized by resonance. This compound will also react with AgNO₃ and give a precipitate.

- **Compound D (1,1-Dichloroethane, CH₃CCl₂H)**:
- When the C-Cl bond breaks, it forms a carbocation that is not as stable as the tertiary carbocation but is still capable of forming. However, if we consider the specific structure, the chlorine is attached to a sp² carbon, which makes the carbocation formed less stable.

3. **Conclusion**:
- Among these compounds, **Compound C (Vinyl chloride)** is the one that forms a carbocation that is unstable due to the nature of the sp² hybridization. Thus, it is unable to give precipitation after reaction with silver nitrate.

### Final Answer:
The organic compound unable to give precipitation after reaction with silver nitrate is **C. CH₂=CHCl (Vinyl chloride)**.

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