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Select the compound(s) that will give only a single monochlorination product in its free radical chlorination when reacted with Cl2 and light or heat?

Select the compound(s) that will give only a single monochlorination product in its free radical chlorination when reacted with Cl2 and light or heat?

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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### Free Radical Chlorination and Selectivity **Question:** Select the compound(s) that will give only a **single** monochlorination product in its free radical chlorination when reacted with Cl₂ and light or heat? **Structural Formulas Presented:** 1. **Structure 1:** A zigzag line representing a simple hydrocarbon. 2. **Structure 2:** A cyclohexane ring. 3. **Structure 3:** A benzene ring. 4. **Structure 4:** A neopentane (a carbon atom bonded to four other carbon atoms). 5. **Structure 5:** An isohexane derivative with two substituents. 6. **Structure 6:** A carbon atom bonded to three other carbon atoms (tertiary carbon) and a methyl group. #### Analysis: For free radical chlorination: - The reaction proceeds by substituting a hydrogen atom with a chlorine atom. - The selectivity depends on the different types of hydrogen atoms present in the molecule. 1. **Structure 1:** Multiple hydrogens on different carbon atoms may lead to multiple products. 2. **Structure 2:** All hydrogen atoms on the cyclohexane ring are equivalent, so only one monochlorinated product is possible. 3. **Structure 3:** Benzene rings generally do not undergo free radical chlorination under normal conditions without catalysts. 4. **Structure 4:** Neopentane has all the hydrogens on equivalent secondary carbon atoms, leading to one possible monochlorinated product. 5. **Structure 5:** The isohexane derivative has more than one type of hydrogen, leading to multiple products. 6. **Structure 6:** Only one type of hydrogen on a tertiary carbon atom is available for substitution, leading to one product. **Conclusion:** Compounds **2 and 4** (cyclohexane and neopentane) will give only a **single** monochlorination product when reacted with Cl₂ and light or heat.
Transcribed Image Text:### Free Radical Chlorination and Selectivity **Question:** Select the compound(s) that will give only a **single** monochlorination product in its free radical chlorination when reacted with Cl₂ and light or heat? **Structural Formulas Presented:** 1. **Structure 1:** A zigzag line representing a simple hydrocarbon. 2. **Structure 2:** A cyclohexane ring. 3. **Structure 3:** A benzene ring. 4. **Structure 4:** A neopentane (a carbon atom bonded to four other carbon atoms). 5. **Structure 5:** An isohexane derivative with two substituents. 6. **Structure 6:** A carbon atom bonded to three other carbon atoms (tertiary carbon) and a methyl group. #### Analysis: For free radical chlorination: - The reaction proceeds by substituting a hydrogen atom with a chlorine atom. - The selectivity depends on the different types of hydrogen atoms present in the molecule. 1. **Structure 1:** Multiple hydrogens on different carbon atoms may lead to multiple products. 2. **Structure 2:** All hydrogen atoms on the cyclohexane ring are equivalent, so only one monochlorinated product is possible. 3. **Structure 3:** Benzene rings generally do not undergo free radical chlorination under normal conditions without catalysts. 4. **Structure 4:** Neopentane has all the hydrogens on equivalent secondary carbon atoms, leading to one possible monochlorinated product. 5. **Structure 5:** The isohexane derivative has more than one type of hydrogen, leading to multiple products. 6. **Structure 6:** Only one type of hydrogen on a tertiary carbon atom is available for substitution, leading to one product. **Conclusion:** Compounds **2 and 4** (cyclohexane and neopentane) will give only a **single** monochlorination product when reacted with Cl₂ and light or heat.
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