Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
Question
Book Icon
Chapter 30.3, Problem 3P
Interpretation Introduction

Interpretation:

Only the 2E,4E isomer is obtained in practice by opening of trans-3,4-Dimethylcyclobutene by two conrotatory paths to give symmetry-allowed products either (2E,4E)-2,4-hexadiene or (2Z,4Z)-2,4-hexadiene.

Concept introduction:

An electrocyclic ring-opening reaction is a reaction in which a σ bond of a cyclic reactant is cleaved to form a conjugated product with one more π bond. It occurs only when like phases of orbitals can overlap to form a bond. Such a reaction is symmetry allowed. It cannot occur between orbitals of opposite phase. Such a reaction is symmetry forbidden. To form a bond, the p orbitals on the terminal carbons must rotate so that like phases can interact to form the new sigma bond. Two modes of rotation are possible - When like phases of the p orbitals are on the same side of the molecule, the two orbitals must rotate in opposite direction one clockwise and one counterclockwise. Rotation in opposite directions is said to be disrotatory.

When like phases of the p orbitals are on opposite sides of the molecule, the two orbitals must rotate in the same direction both clockwise or both counterclockwise. Rotation in the same direction is said to be conrotatory.

Blurred answer
Students have asked these similar questions
Consider the structure (6R,7S)-6,7-dimethyl-1,2,3,4,6,7-hexahydronaphthalene of (6R,7S)-6,7-dimethyl-1,2,3,4,6,7-hexahydronaphthalene, which can undergo an electrocyclic ring opening. The concerted electron shifts result in a highly stereoselective product. The configuration of the product depends on whether it is a thermal reaction or a photochemical reaction. Predict the thermal and photochemical outcomes of this reaction. Draw the thermal product. Draw the photochemical product. Erase Select Draw Rings More Erase Select Draw Rings More
Identify the s-trans conformation of (3Z,5Z)–4,5–dimethyldeca-3,5-diene.
Identify the s-cis conformation of (3Z,5Z)-4,5-dimethyldeca-3,5-diene.
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • 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
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning