Organic Chemistry As a Second Language: First Semester Topics
Organic Chemistry As a Second Language: First Semester Topics
4th Edition
ISBN: 9781119110668
Author: David R. Klein
Publisher: WILEY
Question
Book Icon
Chapter 10.3, Problem 10.7P
Interpretation Introduction

Interpretation:

The major product that is expected has to be drawn when the given compound is treated with ethoxide to give an E2 reaction.

Concept Introduction:

Elimination reactions are the one in which the groups are lost and the saturated bonds are converted to unsaturated bonds.  Usually the substitution reaction compete with elimination reaction.

Organic Chemistry As a Second Language: First Semester Topics, Chapter 10.3, Problem 10.7P , additional homework tip  1

In elimination reaction, the beta proton is removed together with the leaving group to form a double bond.

E2 reaction proceeds through a single step without any formation of intermediates.  The base abstracts a proton form the substrate and the loss of leaving group also happens resulting in the formation of double bond.  E2 stands for bimolecular elimination.

The proton can be abstracted by the base in two different ways leading to a regiochemical outcome.  In the given reaction below, two alkenes are formed as products due to regiochemistry.

Organic Chemistry As a Second Language: First Semester Topics, Chapter 10.3, Problem 10.7P , additional homework tip  2

The two alkenes that are formed can be given different names.  If the alkene is more substituted means it is known as Zaitsev product, and if the alkene formed is less substituted means it is known as Hofmann product.  Generally more substituted product is the major product (Zaitsev product).

If the reaction is performed with a sterically hindered base, the major product will be less substituted alkene (Hofmann product).  The regiochemical outcome can be decided by choosing the base.  Some of the sterically hindered bases are,

Organic Chemistry As a Second Language: First Semester Topics, Chapter 10.3, Problem 10.7P , additional homework tip  3

Blurred answer
Students have asked these similar questions
5. A solution of sucrose is fermented in a vessel until the evolution of CO2 ceases. Then, the product solution is analyzed and found to contain, 45% ethanol; 5% acetic acid; and 15% glycerin by weight. If the original charge is 500 kg, evaluate; e. The ratio of sucrose to water in the original charge (wt/wt). f. Moles of CO2 evolved. g. Maximum possible amount of ethanol that could be formed. h. Conversion efficiency. i. Per cent excess of excess reactant. Reactions: Inversion reaction: C12H22O11 + H2O →2C6H12O6 Fermentation reaction: C6H12O6 →→2C2H5OH + 2CO2 Formation of acetic acid and glycerin: C6H12O6 + C2H5OH + H₂O→ CH3COOH + 2C3H8O3
Show work. don't give Ai generated solution.  How many carbons and hydrogens are in the structure?
13. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. cleavage Bond A •CH3 + 26.← Cleavage 2°C. + Bond C +3°C• CH3 2C Cleavage E 2°C. 26. weakest bond Intact molecule Strongest 3°C 20. Gund Largest argest a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. C Weakest bond A Produces Most Bond Strongest Bond Strongest Gund produces least stable radicals Weakest Stable radical b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 13°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. • CH3 methyl radical Formed in Gund A Cleavage c.…
Knowledge Booster
Background pattern image
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