To determine which of the given compounds is chiral, we need to identify if any of them possess a chiral center. A chiral center is typically a carbon atom that is bonded to four different groups, resulting in non-superimposable mirror images.
### Step-by-Step Solution:
1. **Understand Chiral Centers**:
- A chiral center is usually a carbon atom that has four different substituents. This results in two non-superimposable mirror images, also known as enantiomers.
2. **Analyze the First Compound (1,1-dibromo-1-chloropropane)**:
- Structure: CH2Br, CHBr, CH3
- In this compound, the first carbon has two bromine atoms attached and one chlorine atom. Since there are two identical bromine atoms, this carbon does not have four different groups.
- **Conclusion**: This compound is not chiral.
3. **Analyze the Second Compound (1,3-dibromo-1-chloropropane)**:
- Structure: CHBr, CH2, CHBr
- The first carbon has one bromine, one chlorine, one hydrogen, and the second carbon has two hydrogen atoms. The first carbon does not have four different groups due to the presence of two bromine atoms.
- **Conclusion**: This compound is not chiral.
4. **Analyze the Third Compound (1,1-dibromo-3-chloropropane)**:
- Structure: CH2Br, CH2, CHCl
- The first carbon has two bromine atoms, and the third carbon has one chlorine and two hydrogen atoms. Again, the first carbon does not have four different groups.
- **Conclusion**: This compound is not chiral.
5. **Analyze the Fourth Compound (1,3-dibromo-2-chloropropane)**:
- Structure: CHBr, CHCl, CHBr
- The second carbon has one chlorine, one bromine, one hydrogen, and one carbon chain. This carbon has four different groups attached to it.
- **Conclusion**: This compound is chiral.
### Final Answer:
The chiral compound among the options is **1,3-dibromo-2-chloropropane**.
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