Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
Question
Book Icon
Chapter 3.9, Problem 3.11TIY
Interpretation Introduction

Interpretation:Whether monochlorination or monobromination of 2,3-Dimethylbutane would be synthetically useful procedure or not should be determined.

Concept introduction: The monobromination or monochlorination performed with ultraviolet light proceeds via radical chain mechanism.

In the halogenation reaction, the reactivity of tertiary C-H bond is higher than that of secondary which is further higher than primary C-H bonds.

This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.In case of tertiary radical, the maximum amount of hyperconjugation can occur because of nine adjacent C – H bonds. Thus the extent of delocalization is greatest in tertiary; thus tertiary radicals have more tendencies to form. In primary number of immediate adjacent hydrogen left after C – H bond cleavage is only two and least hyperconjugation makes it least reactive.

Blurred answer
Students have asked these similar questions
You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products: xi 1. ☑ 2. H₂O хе i Draw the missing reagent X you think will make this synthesis work in the drawing area below. If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. There is no reagent that will make this synthesis work without complications. : ☐ S ☐
Predict the major products of this organic reaction: H OH 1. LiAlH4 2. H₂O ? Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry. Click and drag to start drawing a structure. G C टे
For each reaction below, decide if the first stable organic product that forms in solution will create a new C-C bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. NH2 CI MgCl ? Will the first product that forms in this reaction create a new CC bond? Yes No MgBr ? Will the first product that forms in this reaction create a new CC bond? Yes No G टे
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning