се Which is most acidic? SH SH I 1 се 4 SH cl 2 c cl SH Ÿ 5 SH се се 3

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**Which is most acidic?**

This image presents five chemical structures labeled from 1 to 5, each featuring a thiol group (-SH). The task is to determine which compound is the most acidic. Let's examine each compound:

1. **Structure 1**: A simple alkane with an -SH group, featuring an iodine (I) substituent on a carbon atom adjacent to the -SH group.
   
2. **Structure 2**: An alkane with an -SH group, featuring a single chlorine (Cl) atom on a carbon adjacent to the -SH group.
   
3. **Structure 3**: An alkane with an -SH group, featuring two chlorine (Cl) atoms on a carbon adjacent to the -SH group.
   
4. **Structure 4**: An alkane with an -SH group, featuring two chlorine (Cl) atoms, each on separate carbon atoms adjacent to the -SH group.

5. **Structure 5**: An alkane with an -SH group, featuring three chlorine (Cl) atoms, two on one carbon and one on another carbon adjacent to the -SH group.

To determine acidity, consider the electron-withdrawing effects of substituents:
- Electron-withdrawing groups such as chlorine can increase acidity by stabilizing negative charge on the conjugate base.
- Multiple chlorine atoms will increase this effect.

Therefore, more chlorine atoms near the thiol likely increase the acidity: Structure 5, which has three chlorines, is expected to be the most acidic.
Transcribed Image Text:**Which is most acidic?** This image presents five chemical structures labeled from 1 to 5, each featuring a thiol group (-SH). The task is to determine which compound is the most acidic. Let's examine each compound: 1. **Structure 1**: A simple alkane with an -SH group, featuring an iodine (I) substituent on a carbon atom adjacent to the -SH group. 2. **Structure 2**: An alkane with an -SH group, featuring a single chlorine (Cl) atom on a carbon adjacent to the -SH group. 3. **Structure 3**: An alkane with an -SH group, featuring two chlorine (Cl) atoms on a carbon adjacent to the -SH group. 4. **Structure 4**: An alkane with an -SH group, featuring two chlorine (Cl) atoms, each on separate carbon atoms adjacent to the -SH group. 5. **Structure 5**: An alkane with an -SH group, featuring three chlorine (Cl) atoms, two on one carbon and one on another carbon adjacent to the -SH group. To determine acidity, consider the electron-withdrawing effects of substituents: - Electron-withdrawing groups such as chlorine can increase acidity by stabilizing negative charge on the conjugate base. - Multiple chlorine atoms will increase this effect. Therefore, more chlorine atoms near the thiol likely increase the acidity: Structure 5, which has three chlorines, is expected to be the most acidic.
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