31. Which mechanism is correct for the following intramolecular substitution reaction? (a) (b) (c) H N: H H₂N. OH H. H N: CI NaOH jeze OH *-= NH H H — NH NH OH NH
31. Which mechanism is correct for the following intramolecular substitution reaction? (a) (b) (c) H N: H H₂N. OH H. H N: CI NaOH jeze OH *-= NH H H — NH NH OH NH
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...
Related questions
Question
![**Question 31:**
**Which mechanism is correct for the following intramolecular substitution reaction?**
**Reaction:**
\[ \text{H}_2\text{N}(CH_2)_5\text{Cl} \], when treated with \(\text{NaOH}\), forms a cyclic amine.
**Mechanism Options:**
**(a) Mechanism:**
1. The hydroxide ion (\( \text{OH}^- \)) deprotonates the amine group.
2. The deprotonated nitrogen attacks the carbon with the chlorine, resulting in the formation of a six-membered ring and the expulsion of chloride ion.
**(b) Mechanism:**
1. The formation of a protonated nitrogen intermediate.
2. Cyclization occurs through the positively charged nitrogen, forming a cyclic ammonium ion.
3. The hydroxide ion (\( \text{OH}^- \)) deprotonates the nitrogen to produce the final cyclic amine.
**(c) Mechanism:**
1. The intramolecular nucleophilic substitution occurs directly, forming a cyclic ammonium ion.
2. The hydroxide ion (\( \text{OH}^- \)) deprotonates the cyclic ammonium ion to yield the cyclic amine.
_The problem provides three possible mechanisms for converting a linear compound to a cyclic amine via intramolecular substitution, involving the deprotonation and cyclization steps._](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F2be6fcbd-7549-49b0-80f8-3663999fa2f7%2Fa6e2dcf2-f561-4304-9ee5-c4ecb99c0006%2F61s01jf_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Question 31:**
**Which mechanism is correct for the following intramolecular substitution reaction?**
**Reaction:**
\[ \text{H}_2\text{N}(CH_2)_5\text{Cl} \], when treated with \(\text{NaOH}\), forms a cyclic amine.
**Mechanism Options:**
**(a) Mechanism:**
1. The hydroxide ion (\( \text{OH}^- \)) deprotonates the amine group.
2. The deprotonated nitrogen attacks the carbon with the chlorine, resulting in the formation of a six-membered ring and the expulsion of chloride ion.
**(b) Mechanism:**
1. The formation of a protonated nitrogen intermediate.
2. Cyclization occurs through the positively charged nitrogen, forming a cyclic ammonium ion.
3. The hydroxide ion (\( \text{OH}^- \)) deprotonates the nitrogen to produce the final cyclic amine.
**(c) Mechanism:**
1. The intramolecular nucleophilic substitution occurs directly, forming a cyclic ammonium ion.
2. The hydroxide ion (\( \text{OH}^- \)) deprotonates the cyclic ammonium ion to yield the cyclic amine.
_The problem provides three possible mechanisms for converting a linear compound to a cyclic amine via intramolecular substitution, involving the deprotonation and cyclization steps._
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 3 steps
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY