Bundle: Organic Chemistry, 9th, Loose-Leaf + OWLv2, 4 terms (24 months) Printed Access Card
Bundle: Organic Chemistry, 9th, Loose-Leaf + OWLv2, 4 terms (24 months) Printed Access Card
9th Edition
ISBN: 9781305701021
Author: John E. McMurry
Publisher: Cengage Learning
Question
Book Icon
Chapter 30.SE, Problem 21AP
Interpretation Introduction

Interpretation:

Whether the cyclization and formation of a bicyclic product when (1Z,3Z,5Z)- 1,3,5-cyclononatriene is heated at 100ºC takes place in conrotatory or disrotatory manner is to be identified. Further the stereochemical relationship of the two hydrogens at the ring junction, cis or trans is to be stated.

Concept introduction:

An electrocyclic reaction involves the cyclization of a conjugated acyclic system. These reactions are reversible and are highly stereospecific.

In elecrocyclic reactions involving even number of electron pairs, a thermal reaction occurs in conrotatory manner and a photochemical reaction occurs in disrotatory manner.

In elecrocyclic reactions involving odd number of electron pairs, a thermal reaction occurs in disrotatory manner and a photochemical reaction occurs in conrotatory manner.

To identify:

Whether the cyclization and formation of a bicyclic product when (1Z,3Z,5Z)- 1,3,5-cyclononatriene is heated at 100ºC takes place in conrotatory or disrotatory manner.

To state:

The stereochemical relationship of the two hydrogens at the ring junction, cis or trans.

Blurred answer
Students have asked these similar questions
4. C6H100 5 I peak 3 2 PPM Integration values: 1.79ppm (2), 4.43ppm (1.33) Ipeak
None
3. Consider the compounds below and determine if they are aromatic, antiaromatic, or non-aromatic. In case of aromatic or anti-aromatic, please indicate number of I electrons in the respective systems. (Hint: 1. Not all lone pair electrons were explicitly drawn and you should be able to tell that the bonding electrons and lone pair electrons should reside in which hybridized atomic orbital 2. You should consider ring strain- flexibility and steric repulsion that facilitates adoption of aromaticity or avoidance of anti- aromaticity) H H N N: NH2 N Aromaticity (Circle) Aromatic Aromatic Aromatic Aromatic Aromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic nonaromatic nonaromatic nonaromatic nonaromatic nonaromatic aromatic TT electrons Me H Me Aromaticity (Circle) Aromatic Aromatic Aromatic Aromatic Aromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic nonaromatic nonaromatic nonaromatic nonaromatic nonaromatic aromatic πT electrons H HH…
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