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
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Chapter 4, Problem 30P

(a)

Interpretation Introduction

Interpretation:The strain energy determined in prismane should be compared to two three membered and three four membered rings.

Concept introduction:Ring strain is a kind of instability that results when bonds deviate from ideal bond-angle. The cyclic system have different amount of strain as illustrated below:

  Organic Chemistry: Structure and Function, Chapter 4, Problem 30P , additional homework tip  1

It is evident that three and four membered small ring systems have considerable degree of angular and ring strain that leads to their instability. Therefore it can be concluded that as one moves to higher order cycloalkanes, ring size expands and strain diminishes.

(b)

Interpretation Introduction

Interpretation:The estimated strain energy released when one side of three membered ring is broken should be determined.

Concept introduction:Ring strain is a kind of instability that results when bonds deviate from ideal bond-angle. The cyclic system have different amount of strain as illustrated below:

  Organic Chemistry: Structure and Function, Chapter 4, Problem 30P , additional homework tip  2

It is evident that three and four membered small ring systems have considerable degree of angular and ring strain that leads to their instability. Therefore it can be concluded that as one moves to higher order cycloalkanes, ring size expands and strain diminishes.

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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License