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Ch.4 Introduction to Organic Compounds
Frost - General, Organic and Biological Chemistry 4th Edition
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Not the one you use?Change textbook
Chapter 1, Problem 61

Using condensed structural formulas, draw three conformers of hexane.

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1
Start by understanding that hexane is a linear alkane with the molecular formula C_6H_14. It consists of a chain of six carbon atoms, each bonded to sufficient hydrogen atoms to satisfy the tetravalency of carbon.
Recognize that conformers are different spatial arrangements of a molecule that result from rotation around single bonds. In hexane, these rotations occur around the C-C single bonds.
Draw the most extended conformer of hexane, which is the 'staggered' conformation. This is where all the carbon-carbon bonds are in a zig-zag pattern, minimizing steric hindrance.
Next, draw a 'gauche' conformer by rotating one of the C-C bonds so that two of the methyl groups (CH_3) are closer together, creating a slight steric interaction.
Finally, draw an 'eclipsed' conformer where the hydrogen atoms on adjacent carbons are aligned, leading to increased torsional strain. This is less stable than the staggered conformer.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Conformers

Conformers, or conformational isomers, are different spatial arrangements of a molecule that can be interconverted by rotation around single bonds. In the case of hexane, which has multiple carbon-carbon single bonds, various conformers can be visualized by rotating these bonds, leading to distinct shapes that affect the molecule's properties and interactions.
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Condensed Structural Formulas

Condensed structural formulas provide a simplified representation of a molecule's structure, showing how atoms are connected without depicting all the bonds explicitly. For hexane, a condensed formula like CH3(CH2)4CH3 indicates the arrangement of carbon and hydrogen atoms, allowing for easier visualization of different conformers while maintaining clarity about the molecular structure.
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Hexane

Hexane is a straight-chain alkane with the chemical formula C6H14, consisting of six carbon atoms connected by single bonds. Its structure allows for various conformations due to the flexibility of the carbon-carbon bonds, making it a common example in organic chemistry for studying conformational analysis and molecular geometry.
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