Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 4: 4-20 (page 112)

Which isomer is more stable, cis-decalin or trans-decalin? Explain.

Short Answer

Expert verified

Trans-decalin is more stable as it shows fewer steric interactions.

Step by step solution

01

Cis and trans conformation of decalin

In cis-decalin, the hydrogen atoms at the bridgehead carbons are on the same face of the rings; in trans-decalin, the bridgehead hydrogens are on opposite faces.

02

Axial and equatorial positions

Axial bonds are the bonds that are perpendicular or vertical to the ring plane. Equatorial bonds are approximately horizontal in the plane of the ring.

03

Conformation stability

Cis- and trans-decalin, respectively

Trans-decalin is more stable than cis-decalin because the rings are at a maximum distance in trans-decalin, and in cis-decalin show steric interactions and hence, decreases its stability.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Give IUPAC names for the following cycloalkanes

One of the two chair structures of cis-1-chloro-3-methylcyclohexane is more stable than the other by 15.5 kJ/mol (3.7 kcal/mol). Which is it? What is the energy cost of a 1,3-diaxial interaction between chlorine and a methyl group?

Two conformations of cis-1,3-dimethylcyclobutane are shown. What is the difference between them, and which do you think is likely to be more stable?

Why do you suppose an axial cyano (–CN) substituent causes practically no 1,3-diaxial steric strain (0.4 kJ/mol)? Use molecular models to help with your answer.

Look at Figure 4-12 on page 105, and estimate the percentages of axial andequatorial conformations present at equilibrium in bromocyclohexane.
See all solutions

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Read Explanation

Chemical Analysis

Read Explanation

Kinetics

Read Explanation

Making Measurements

Read Explanation

Ionic and Molecular Compounds

Read Explanation

The Earths Atmosphere

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free