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The bristlecone pine is the oldest living organism on Earth. The waxy coating on its needles contains a mixture of organic compounds called alkanes, the subject of this chapter.

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FIGURE 3-1 The reactions of ethylene and menthene with bromine. In both molecules, the carbon–carbon double-bond functional group has a similar polarity pattern, so both molecules react with Br2 in the same way. The size and complexity of the molecules are not important.

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FIGURE 3-2 Some representations of butane, C4H10. The molecule is the same regardless of how it’s drawn. These structures imply only that butane has a continuous chain of four carbon atoms; they do not imply any specific geometry.

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FIGURE 3-3 Alkyl groups generated from straight-chain alkanes.

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FIGURE 3-4 A plot of melting and boiling points versus number of carbon atoms for the C1–C14 straight-chain alkanes. There is a regular increase with molecular size.

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FIGURE 3-5 Rotation occurs around the carbon–carbon single bond in ethane because of s bond cylindrical symmetry.

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FIGURE 3-6 A sawhorse representation and a Newman projection of ethane. The sawhorse representation views the molecule from an oblique angle, while the Newman projection views the molecule end-on. Note that the molecular model of the Newman projection appears at first to have six atoms attached to a single carbon. Actually, the front carbon, with three attached green atoms, is directly in front of the rear carbon, with three attached red atoms.

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FIGURE 3-7 A graph of potential energy versus bond rotation in ethane. The staggered conformations are 12 kJ/mol lower in energy than the eclipsed conformations.

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FIGURE 3-8 Newman projections of propane showing staggered and eclipsed conformations. The staggered conformer is lower in energy by 14 kJ/mol.

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FIGURE 3-9 A plot of potential energy versus rotation for the C2–C3 bond in butane. The energy maximum occurs when the two methyl groups eclipse each other, and the energy minimum occurs when the two methyl groups are 180° apart (anti).

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FIGURE 3-10 The most stable alkane conformation is the one in which all substituents are staggered and the carbon–carbon bonds are arranged anti, as shown in this model of decane.

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Gasoline is a finite resource. It won’t be around forever.

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