For each pair of substrates below, choose the one that will react faster in a substitution reaction, assuming that: 1. the rate of substitution doesn't depend on nucleophile concentration and 2. the products are a roughly 50/50 mixture of enantiomers. Substrate A Xa CI Substrate B R. you Faster Rate (Choose one) (Choose one) (Choose one)
For each pair of substrates below, choose the one that will react faster in a substitution reaction, assuming that: 1. the rate of substitution doesn't depend on nucleophile concentration and 2. the products are a roughly 50/50 mixture of enantiomers. Substrate A Xa CI Substrate B R. you Faster Rate (Choose one) (Choose one) (Choose one)
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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![**Substitution Reactions: Predicting the Effect of Carbocation Stability on the Rate of Reaction**
In this activity, for each pair of substrates, select the one that will react faster in a substitution reaction. Assume that:
1. The rate of substitution doesn’t depend on nucleophile concentration.
2. The products are a roughly 50/50 mixture of enantiomers.
### Substrate Comparison
**1. Substrate A vs. Substrate B**
- **Substrate A**: Illustrated as a structure with an iodine atom attached.
- **Substrate B**: Illustrated as a cyclic compound with a chlorine atom attached.
- **Faster Rate Choice**: [Dropdown menu for selection]
**2. Substrate C vs. Substrate D**
- **Substrate C**: Structure with a chlorine atom attached to a benzene ring.
- **Substrate D**: Illustrated as a structure with a chlorine atom attached to an alkene.
- **Faster Rate Choice**: [Dropdown menu for selection]
Use your knowledge of carbocation stability, stereochemistry, and reactivity in substitution reactions to make your selections.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F593e4a4c-a9fc-4231-bacd-fbc9affb1612%2F42821ff1-093d-4aa3-b9dc-898d96b5a19d%2Fhnomdt_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Substitution Reactions: Predicting the Effect of Carbocation Stability on the Rate of Reaction**
In this activity, for each pair of substrates, select the one that will react faster in a substitution reaction. Assume that:
1. The rate of substitution doesn’t depend on nucleophile concentration.
2. The products are a roughly 50/50 mixture of enantiomers.
### Substrate Comparison
**1. Substrate A vs. Substrate B**
- **Substrate A**: Illustrated as a structure with an iodine atom attached.
- **Substrate B**: Illustrated as a cyclic compound with a chlorine atom attached.
- **Faster Rate Choice**: [Dropdown menu for selection]
**2. Substrate C vs. Substrate D**
- **Substrate C**: Structure with a chlorine atom attached to a benzene ring.
- **Substrate D**: Illustrated as a structure with a chlorine atom attached to an alkene.
- **Faster Rate Choice**: [Dropdown menu for selection]
Use your knowledge of carbocation stability, stereochemistry, and reactivity in substitution reactions to make your selections.
Expert Solution
Step 1
note 1: The reaction rate of substitution doesn't depend on nucleophile concentration
note 2: the product is a roughly 50:50 mixture.
This suggested that the substation reaction goes through the sn1 pathway.
The rate of the sn1 reaction depends on carbonation stability.
More stable carbocation gives a faster rate of reaction.
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