Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
bartleby

Concept explainers

Question
Book Icon
Chapter 28, Problem 35P
Interpretation Introduction

Interpretation:

The two product in the given reaction are formed after [1, 7] sigmatropic rearrangement, one due to hydrogen migration and the other to deuterium migration.  It should be represented the configuration of product by replacing the A and B with appropriate atoms (H or D)

Concept introduction:

In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”

Organic Chemistry (8th Edition), Chapter 28, Problem 35P , additional homework tip  1

Sigma tropic rearrangement reactions are designated with digits.  For example a [1, 3] sigma tropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for sigma tropic rearrangement reactions are listed below

SumofthenumberofbondsinthereactingsytemsofbothreagentsReactionconditionsAllowedmodeofbond formationEvennumberThermalAntarafacialPhotochemicalSuprafacialOddnumberThermalSuprafacialPhotochemicalAntarafacial

Migration of carbon and hydrogen will occur in a sigmatropic rearrangement reaction.  Migration of hydrogen in suprafacial and antarafacial rearrangement can be represented as follows,

Organic Chemistry (8th Edition), Chapter 28, Problem 35P , additional homework tip  2Organic Chemistry (8th Edition), Chapter 28, Problem 35P , additional homework tip  3

Carbon migrating with one lobe of its p orbital interacting

Organic Chemistry (8th Edition), Chapter 28, Problem 35P , additional homework tip  4 Organic Chemistry (8th Edition), Chapter 28, Problem 35P , additional homework tip  5

Carbon migrating with both lobe of its p orbital interacting

Organic Chemistry (8th Edition), Chapter 28, Problem 35P , additional homework tip  6Organic Chemistry (8th Edition), Chapter 28, Problem 35P , additional homework tip  7

Blurred answer
Students have asked these similar questions
A 0.10 M solution of acetic acid (CH3COOH, Ka = 1.8 x 10^-5) is titrated with a 0.0250 M solution of magnesium hydroxide (Mg(OH)2). If 10.0 mL of the acid solution is titrated with 10.0 mL of the base solution, what is the pH of the resulting solution?
Firefly luciferin exhibits three rings. Identify which of the rings are aromatic. Identify which lone pairs are involved in establishing aromaticity. The lone pairs are labeled A-D below.
A 0.10 M solution of acetic acid (CH3COOH, Ka = 1.8 x 10^-5) is titrated with a 0.0250 M solution of magnesium hydroxide (Mg(OH)2). If 10.0 mL of the acid solution is titrated with 10.0 mL of the base solution, what is the pH of the resulting solution?
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
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
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
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning