Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
Bartleby Related Questions Icon

Related questions

bartleby

Concept explainers

Question
R
The mechanism involves the following 5 steps:
haloketone with base to yield a ring-contracted product.
1. Abstraction of a proton to form enolate anion 1;
2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion;
3. Addition of hydroxide ion to form tetrahedral intermediate 3;
4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4;
5. Proton transfer to form the rearranged carboxylic acid.
For the following reaction, draw the reaction out on paper and then draw the structure of cyclopropanone intermediate 2 in the window.
CO₂H
CI
8 5
base
. You do not have to consider stereochemistry.
. You do not have to explicitly draw H atoms.
. Do not include lone pairs in your answer. They will not be considered in the grading.
. Do not include counter-ions, e.g., Na, I, in your answer.
*****
O. Sn [F
expand button
Transcribed Image Text:R The mechanism involves the following 5 steps: haloketone with base to yield a ring-contracted product. 1. Abstraction of a proton to form enolate anion 1; 2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion; 3. Addition of hydroxide ion to form tetrahedral intermediate 3; 4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4; 5. Proton transfer to form the rearranged carboxylic acid. For the following reaction, draw the reaction out on paper and then draw the structure of cyclopropanone intermediate 2 in the window. CO₂H CI 8 5 base . You do not have to consider stereochemistry. . You do not have to explicitly draw H atoms. . Do not include lone pairs in your answer. They will not be considered in the grading. . Do not include counter-ions, e.g., Na, I, in your answer. ***** O. Sn [F
Expert Solution
Check Mark
Knowledge Booster
Background pattern image
Chemistry
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.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY