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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![**Question 5:** Explain why the nitrogen on the molecule on the left below is more reactive as a nucleophile than the other molecule's nitrogen atom.
**Molecular Structures:**
The diagram shows two molecular structures for comparison:
1. **Left Molecule:**
- Structure: A carbon double-bonded to an oxygen (carbonyl group) and single-bonded to a nitrogen with a negative charge.
2. **Right Molecule:**
- Structure: A nitrogen with a negative charge, connected to two hydrogen atoms and an ethyl group.
**Explanation:**
The nitrogen in the molecule on the left is more reactive as a nucleophile because the presence of the carbonyl group (C=O) withdraws electron density through resonance and inductive effects. This stabilization of the negative charge on the nitrogen by resonance makes it a stronger nucleophile, as the nitrogen is more likely to donate its lone pair of electrons to an electrophile. In contrast, the nitrogen in the right molecule lacks such stabilizing interactions, making it less nucleophilic.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fa190c71f-88db-4d03-811f-4518a93048d6%2F2ba0875d-23ce-4b6d-95f6-a304828257d4%2F4g788k_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Question 5:** Explain why the nitrogen on the molecule on the left below is more reactive as a nucleophile than the other molecule's nitrogen atom.
**Molecular Structures:**
The diagram shows two molecular structures for comparison:
1. **Left Molecule:**
- Structure: A carbon double-bonded to an oxygen (carbonyl group) and single-bonded to a nitrogen with a negative charge.
2. **Right Molecule:**
- Structure: A nitrogen with a negative charge, connected to two hydrogen atoms and an ethyl group.
**Explanation:**
The nitrogen in the molecule on the left is more reactive as a nucleophile because the presence of the carbonyl group (C=O) withdraws electron density through resonance and inductive effects. This stabilization of the negative charge on the nitrogen by resonance makes it a stronger nucleophile, as the nitrogen is more likely to donate its lone pair of electrons to an electrophile. In contrast, the nitrogen in the right molecule lacks such stabilizing interactions, making it less nucleophilic.
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