CHEM 262 ORG CHEM EBOOK DIGITAL DELIVERY
CHEM 262 ORG CHEM EBOOK DIGITAL DELIVERY
8th Edition
ISBN: 2818440043505
Author: Bruice
Publisher: PEARSON
Question
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Chapter 28, Problem 30P

(a)

Interpretation Introduction

Interpretation: It should be determined that the given reaction takes place whether by a concerted mechanism or not.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or brocken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

  1. 1) Electrocyclic reactions
  2. 2) Cycloaddition reactions
  3. 3) Sigmatropic reactions

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

CHEM 262 ORG CHEM EBOOK DIGITAL DELIVERY, Chapter 28, Problem 30P , additional homework tip  1

Sigmatropic rearrangement reactions are named with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

(b)

Interpretation Introduction

Interpretation: It should be determined that the given reaction takes place whether by a concerted mechanism or not.

Concept introduction:

Pericyclic reactions are “ any concerted reaction in which bonds are formed or brocken in a cyclic transition state”. There is a single transition state from start to finish, in contrast to a stepwise reaction.

There are mainly three types of pericyclic reactions,

  1. 1) Electrocyclic reactions
  2. 2) Cycloaddition reactions
  3. 3) Sigmatropic reactions

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

CHEM 262 ORG CHEM EBOOK DIGITAL DELIVERY, Chapter 28, Problem 30P , additional homework tip  2

Sigmatropic rearrangement reactions are named with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

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1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.
3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in the reactant before being able to draw the arrows corresponding to product formation. A. B. Rearrangement ΘΗ
2. Draw the arrows required to make the following reactions occur. Please ensure your arrows point from exactly where you want to exactly where you want. If it is unclear from where arrows start or where they end, only partial credit will be given. Note: You may need to draw in lone pairs before drawing the arrows. A. B. H-Br 人 C Θ CI H Cl Θ + Br O
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