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The reaction of 2-bromopropane and sodium ethoxide in ethanol reacts 6.7 times 1). faster than 2-bromo-1-deuteriopropane under the same conditions. Explain what mechanism this data is consistent with, and why. H(D) ELOH Br 2) the following reactions. Explain the reason(s) for the difference in relative rates and regiochemistry in Fast Slow EtO EtO ETOH ETOH

The reaction of 2-bromopropane and sodium ethoxide in ethanol reacts 6.7 times 1). faster than 2-bromo-1-deuteriopropane under the same conditions. Explain what mechanism this data is consistent with, and why. H(D) ELOH Br 2) the following reactions. Explain the reason(s) for the difference in relative rates and regiochemistry in Fast Slow EtO EtO ETOH ETOH

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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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### Educational Content #### 1. Reaction Rate and Mechanism The reaction of 2-bromopropane with sodium ethoxide in ethanol occurs 6.7 times faster than with 2-bromo-1-deuterio propane under the same conditions. This suggests a significant kinetic isotope effect, which is typical for reactions involving the breaking of a C-H bond in the rate-determining step. **Reaction Diagram:** - **Reactant:** 2-bromopropane with a bromine atom (Br) and a hydrogen/deuterium atom (H/D) on a secondary carbon. - **Reagent:** Sodium ethoxide (EtONa) in ethanol (EtOH). - **Product:** An alkene formed after the elimination of HBr. **Explanation Required:** Discuss the mechanism consistent with this observation and why the presence of deuterium affects the rate. #### 2. Relative Rates and Regiochemistry **Reaction 1 (Fast):** - **Reactant:** A cyclohexane derivative with a chlorine atom (Cl) on a secondary carbon. - **Reagent:** Ethoxide ion (EtO-) in ethanol (EtOH). - **Product:** An alkene via an elimination reaction. **Reaction 2 (Slow):** - **Reactant:** Similar cyclohexane derivative as above but with a different orientation. - **Reagent:** Ethoxide ion (EtO-) in ethanol (EtOH). - **Product:** An alkene with a differing regiochemical outcome compared to Reaction 1. **Graph Explanation:** The diagram shows two parallel reactions starting from similar substrates but differing in reaction rate and regiochemistry. The first reaction is labeled "Fast," and the resulting alkene formation suggests a more favorable stereochemistry or less steric hindrance. The second reaction is "Slow," indicating less favorable conditions, possibly due to greater steric hindrance or an unfavorable lying transition state. **Explanation Required:** Discuss the reasons for differences in the relative reaction rates and the observed regiochemistry between the two reactions.
Transcribed Image Text:### Educational Content #### 1. Reaction Rate and Mechanism The reaction of 2-bromopropane with sodium ethoxide in ethanol occurs 6.7 times faster than with 2-bromo-1-deuterio propane under the same conditions. This suggests a significant kinetic isotope effect, which is typical for reactions involving the breaking of a C-H bond in the rate-determining step. **Reaction Diagram:** - **Reactant:** 2-bromopropane with a bromine atom (Br) and a hydrogen/deuterium atom (H/D) on a secondary carbon. - **Reagent:** Sodium ethoxide (EtONa) in ethanol (EtOH). - **Product:** An alkene formed after the elimination of HBr. **Explanation Required:** Discuss the mechanism consistent with this observation and why the presence of deuterium affects the rate. #### 2. Relative Rates and Regiochemistry **Reaction 1 (Fast):** - **Reactant:** A cyclohexane derivative with a chlorine atom (Cl) on a secondary carbon. - **Reagent:** Ethoxide ion (EtO-) in ethanol (EtOH). - **Product:** An alkene via an elimination reaction. **Reaction 2 (Slow):** - **Reactant:** Similar cyclohexane derivative as above but with a different orientation. - **Reagent:** Ethoxide ion (EtO-) in ethanol (EtOH). - **Product:** An alkene with a differing regiochemical outcome compared to Reaction 1. **Graph Explanation:** The diagram shows two parallel reactions starting from similar substrates but differing in reaction rate and regiochemistry. The first reaction is labeled "Fast," and the resulting alkene formation suggests a more favorable stereochemistry or less steric hindrance. The second reaction is "Slow," indicating less favorable conditions, possibly due to greater steric hindrance or an unfavorable lying transition state. **Explanation Required:** Discuss the reasons for differences in the relative reaction rates and the observed regiochemistry between the two reactions.
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