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Physical Properties of Alkanes

Physical Properties of Alkanes

Alkanes are nonpolar molecules due to the presence of only carbon and hydrogen atoms. The electronegativity difference between carbon and hydrogen is minimal, and hence alkanes have a zero dipole moment. This leads to the presence of only dispersion forces between the molecules. The strength of dispersion forces is dependent on the surface area of the molecules on which they act. Since the surface area increases with the molecular length for straight-chain alkanes, the dispersion forces also...

Relative Stabilities of Alkenes

Relative Stabilities of Alkenes

The relative stability of alkenes can be determined by comparing their heats of hydrogenation. The lower heat of hydrogenation indicates the more stable alkene. The three main factors determining the relative stability of alkenes are i) the number of substituents attached to the double-bond carbon atoms, ii) hyperconjugation, and iii) the stereochemistry of the double bond.

Constitutional Isomers of Alkanes

Constitutional Isomers of Alkanes

Organic compounds of the same molecular formula can have different structural formulas called constitutional isomers, and the phenomenon is known as constitutional isomerism. Alkanes with four or more carbons showing multiple structures with the same molecular formula thereby exhibit constitutional isomerism.
The linear isomer of an alkane is prefixed by the term “n”; hence a linear isomer of pentane is known as n-pentane. Based on the type of branching, some of the branched isomers are given...

Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes

Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes

The low reactivity in alkanes can be attributed to the non-polar nature of C–C and C–H σ bonds. Alkanes, therefore, were initially termed as “paraffins,” derived from the Latin words: parum, meaning “too little,” and affinis, meaning “affinity.”
Alkanes undergo combustion in the presence of excess oxygen and high-temperature conditions to give carbon dioxide and water. A combustion reaction is the energy source in natural gas, liquified petroleum gas (LPG), fuel oil, gasoline, diesel fuel, and...

Nomenclature of Alkanes

Nomenclature of Alkanes

In the late 19th-century, the number of new chemical compounds discovered increased tremendously. Hence, the necessity arose to develop a naming system for the systematic nomenclature of these newly discovered compounds. IUPAC (International Union for Pure and Applied Chemistry), established in 1919, sets rules for the nomenclature.
The alkane nomenclature considers the length of the carbon chain, the number, and the location of the substituent to arrive at its systematic name. The IUPAC...

Mass Spectrometry: Branched Alkane Fragmentation

Mass Spectrometry: Branched Alkane Fragmentation

This lesson delves into the mass spectrometry of branched alkane fragmentation. Branched alkanes possess secondary or tertiary carbon atoms, which generate relatively stable carbocations if the cleavage occurs at the branching point. The high stability of carbocations drives the instant fragmentation of branched alkanes. Accordingly, the branched alkane's molecular ion peak is very weak or invisible in the mass spectra, especially in comparison to a linear alkane.

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Related Experiment Video

Updated: Jun 12, 2026

Original Experimental Approach for Assessing Transport Fuel Stability

Original Experimental Approach for Assessing Transport Fuel Stability

Published on: October 21, 2016

Branched alkanes have contrasting stabilities.

Jérôme F Gonthier¹, Matthew D Wodrich, Stephan N Steinmann

¹Laboratory for Computational Molecular Design, Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne, CH-1015 Lausanne, Switzerland.

Organic Letters

|June 5, 2010

Summary

Highly branched alkanes reveal how methyl group arrangements affect stability. Permethylated alkanes are destabilized by bulky methyl groups causing geometric distortions.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Area of Science:

Organic Chemistry
Computational Chemistry
Molecular Interactions

Background:

Understanding substituent effects in alkanes is crucial for predicting molecular stability.
1,3-nonbonded interactions significantly influence molecular conformations and energies.
Previous studies have explored steric and electronic effects in branched hydrocarbons.

Purpose of the Study:

To quantify the stabilizing or destabilizing effects of methyl group patterns in branched alkanes.
To investigate the relationship between molecular geometry and bond separation energies (BSEs).
To elucidate the origins of unique destabilizing features in permethylated alkanes.

Main Methods:

Utilized bond separation reactions to calculate bond separation energies (BSEs).
Analyzed a series of n-, singly methylated, and permethylated alkanes.
Performed computational analysis to correlate BSEs with geometric distortions.

Main Results:

Singly methylated alkanes exhibit positive BSEs, indicating stabilization compared to linear chains.
Permethylated alkanes show decreasing BSEs, suggesting inherent instability.
Destabilization in permethylated alkanes is attributed to steric hindrance from adjacent methyl groups, leading to distorted carbon backbones.

Conclusions:

The spatial arrangement of methyl substituents profoundly impacts alkane stability.
Steric strain, not electronic effects, is the primary driver of instability in highly branched permethylated alkanes.
Bond separation energy analysis provides a valuable metric for assessing nonbonded interactions in hydrocarbons.