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Ch. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testoBruice 8th EditionCh. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and StructureProblema 89
Capitolo 3, Problema 89

Using the data obtained in Problem 85, calculate the amount of steric strain in each of the chair conformers of 1,1,3-trimethylcyclohexane. Which conformer predominates at equilibrium?

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Step 1: Understand the structure of 1,1,3-trimethylcyclohexane. It is a cyclohexane ring with three methyl groups attached: two at the 1-position and one at the 3-position. Cyclohexane can adopt chair conformations, and substituents can occupy axial or equatorial positions.
Step 2: Recall that steric strain arises from interactions between substituents in close proximity. In chair conformations, axial substituents experience 1,3-diaxial interactions with other axial groups on the same side of the ring. Equatorial substituents generally have less steric strain.
Step 3: Analyze the two possible chair conformations of 1,1,3-trimethylcyclohexane. In one conformer, the methyl groups at the 1-position are axial, and the methyl group at the 3-position is equatorial. In the other conformer, the methyl groups at the 1-position are equatorial, and the methyl group at the 3-position is axial.
Step 4: Calculate the steric strain for each conformer by considering the 1,3-diaxial interactions. For the conformer with axial methyl groups at the 1-position, there will be significant steric strain due to interactions with axial hydrogens on the 3-position and 5-position. For the conformer with equatorial methyl groups at the 1-position, steric strain will be minimized as equatorial substituents avoid 1,3-diaxial interactions.
Step 5: Determine which conformer predominates at equilibrium. The conformer with the lower steric strain (equatorial methyl groups at the 1-position) will be more stable and thus predominate at equilibrium. This is because molecules tend to adopt the lowest-energy configuration.

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Chair Conformation

The chair conformation is the most stable form of cyclohexane and its derivatives due to minimized steric strain and torsional strain. In this conformation, the carbon atoms are arranged in a staggered manner, allowing for optimal bond angles and reducing the repulsion between adjacent substituents. Understanding chair conformations is crucial for analyzing the stability of substituted cyclohexanes.
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Understanding what a conformer is.

Steric Strain

Steric strain arises when atoms are forced closer together than their atomic radii allow, leading to increased repulsion between electron clouds. In the context of cyclohexane derivatives, bulky substituents can create steric strain when they occupy axial positions, as they can interact unfavorably with other axial hydrogens. Evaluating steric strain is essential for determining the stability of different conformers.
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What is torsional strain?

Equilibrium and Conformer Predominance

In organic chemistry, equilibrium refers to the state where the rates of formation and breakdown of different conformers are equal. The predominance of a conformer at equilibrium is influenced by factors such as steric strain and torsional strain. Analyzing the energy differences between conformers helps predict which one will be more stable and thus more prevalent in a given system.
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Understanding what a conformer is.
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