Practical aspects of radical halogenation Radical halogenation of ethane is a major industrial proces, thou- sands of tons of chloro- and bromoethane are produced annually. However, radical fluorination and iodination are not practical. Using thermodynamic analysis (similar to one we did in class), explain why radical iodination and fluorination are not practical. Use values in Table 1 for your calculations. Table 1: Bond dissociation energies for various bond types (in kJ/mol) Bond BDE Bond BDE F-F 159 CH3CH2-F CH3CH2 -Cl 456 Cl-C1 243 351 Br- Br 193 CH3CH2- Br 301 I-I 151 CH3CH2 -I 238 Н-F 569 CH3 -H 439 Н-СІ 431 CH3CH2-H 423 (СНH)2СH-Н (СН3)3С-Н Н-Br 366 414 Н-I 299 404 CH2 =CH2 636 CH2 =CH2 (7) 272

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**Practical aspects of radical halogenation**

Radical halogenation of ethane is a major industrial process, with thousands of tons of chloro- and bromoethane produced annually. However, radical fluorination and iodination are not practical.

Using thermodynamic analysis (similar to one we did in class), explain why radical iodination and fluorination are not practical. Use values in Table 1 for your calculations.

**Table 1: Bond dissociation energies for various bond types (in kJ/mol)**

| Bond       | BDE | Bond         | BDE |
|------------|-----|--------------|-----|
| F–F        | 159 | CH₃CH₂–F     | 456 |
| Cl–Cl      | 243 | CH₃CH₂–Cl    | 351 |
| Br–Br      | 193 | CH₃CH₂–Br    | 301 |
| I–I        | 151 | CH₃CH₂–I     | 238 |
| H–F        | 569 | CH₃–H        | 439 |
| H–Cl       | 431 | CH₃CH₂–H     | 423 |
| H–Br       | 366 | (CH₃)₂CH–H   | 414 |
| H–I        | 299 | (CH₃)₃C–H    | 404 |
|            |     | CH₂=CH₂      | 636 |
|            |     | CH₂=CH₂ (π)  | 272 |

The table provides bond dissociation energies (BDE) for various bond types, measured in kilojoules per mole (kJ/mol). These energies can be used to analyze the feasibility of different halogenation processes based on the stability of the bonds involved. Fluorination and iodination present unique challenges due to the specific BDE values for their bonds.
Transcribed Image Text:**Practical aspects of radical halogenation** Radical halogenation of ethane is a major industrial process, with thousands of tons of chloro- and bromoethane produced annually. However, radical fluorination and iodination are not practical. Using thermodynamic analysis (similar to one we did in class), explain why radical iodination and fluorination are not practical. Use values in Table 1 for your calculations. **Table 1: Bond dissociation energies for various bond types (in kJ/mol)** | Bond | BDE | Bond | BDE | |------------|-----|--------------|-----| | F–F | 159 | CH₃CH₂–F | 456 | | Cl–Cl | 243 | CH₃CH₂–Cl | 351 | | Br–Br | 193 | CH₃CH₂–Br | 301 | | I–I | 151 | CH₃CH₂–I | 238 | | H–F | 569 | CH₃–H | 439 | | H–Cl | 431 | CH₃CH₂–H | 423 | | H–Br | 366 | (CH₃)₂CH–H | 414 | | H–I | 299 | (CH₃)₃C–H | 404 | | | | CH₂=CH₂ | 636 | | | | CH₂=CH₂ (π) | 272 | The table provides bond dissociation energies (BDE) for various bond types, measured in kilojoules per mole (kJ/mol). These energies can be used to analyze the feasibility of different halogenation processes based on the stability of the bonds involved. Fluorination and iodination present unique challenges due to the specific BDE values for their bonds.
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