
Concept explainers
Interpretation:
The compound that has the largest heat of combustion has to be identified.
Concept introduction:
Heat of combustion (
Heat of combustion for rings of different sizes: Comparing the rings of different sizes by dividing the heat of combustion by the number of
Ring strain: A type of instability that exists when bonds in a molecule from angles that are abnormal (deviate from ideal bond angles).
Generally, the bonds of larger cycloalkanes can position themselves three dimensionally so as to achieve a conformation that minimizes the total energy of the compound.
Conformations: Rotation about C-C single bonds allows a compound to adopt a variety of possible three-dimensional shapes.
Newman projections: The new conformations of compounds can be drawn and analyzed by Newman projections. A Newman projection visualizes different conformations of Carbon-carbon
The angle between two hydrogens of a Newman projection is called as dihedral angle or torsional angle. This dihedral angle changes as the C-C bond rotates. Two conformations with special attentions are staggered and eclipsed conformation. Staggered conformation is the lowest in energy and the eclipsed conformation is the highest in energy.
For example,
Anti-conformation: The conformation with a dihedral angle of
The two methyl groups achieve maximum separation from each other. In other, methyl groups are closer to each other; their electron clouds are repelling each other, causing an increase in energy. This unfavorable interaction is called gauche interaction.

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Chapter 4 Solutions
Organic Chemistry 3rd.ed. Klein Evaluation/desk Copy
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