Which of the following organic compounds will give a maxiture of 1-chlorobutane and 2-chlorobutance on chlorintaion

Options

A. `CH_(3)-underset(CH_(3))underset(|)CH-CH =CH_(2)`
B. `HC = C-overset(H)overset(|)C = CH_(2)`
C. `CH_(2) =CH-CH=CH_(2)`
D. `CH_(2) =CH-CH_(2)-CH_(3)`

Answer

To determine which organic compound will yield a mixture of 1-chlorobutane and 2-chlorobutane upon chlorination, we need to analyze the structure of the compounds and the mechanism of chlorination.

### Step-by-Step Solution:

1. **Identify the Compounds**:
We need to consider the possible organic compounds that can undergo chlorination to produce both 1-chlorobutane and 2-chlorobutane. The compounds should ideally have a structure that allows for the formation of both products.

2. **Understand Chlorination Mechanism**:
Chlorination typically occurs via a free radical mechanism. In the presence of chlorine (Cl2) and UV light or heat, the hydrogen atoms in the organic compound can be replaced by chlorine atoms.

3. **Analyze Possible Structures**:
- **1-Butene (CH2=CH-CH2-CH3)**: This compound can undergo chlorination to yield both 1-chlorobutane and 2-chlorobutane. The double bond allows for the formation of free radicals that can lead to both products.
- **2-Butene (CH3-CH=CH-CH3)**: This compound can also yield both products upon chlorination because it can form free radicals at both ends of the double bond.
- **Butane (CH3-CH2-CH2-CH3)**: This compound will only yield 1-chlorobutane upon chlorination, as it does not have a double bond.
- **Cyclobutane**: This compound does not have a double bond and will not yield either product.

4. **Conclusion**:
The compounds that can yield both 1-chlorobutane and 2-chlorobutane upon chlorination are 1-butene and 2-butene. Therefore, the answer to the question is either 1-butene or 2-butene.

### Final Answer:
The organic compounds that will give a mixture of 1-chlorobutane and 2-chlorobutane upon chlorination are **1-butene and 2-butene**.