Introductory Organic Chemistry by J.T. Gerig (Auth.)

By J.T. Gerig (Auth.)

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The simplest hydrocarbon is methane, C H 4 . The three-dimensional structure of this molecule is shown in Fig. 1. Each hydrogen atom is located at a corner of a regular tetrahedron so that the atomic orbitals used by the central carbon atom to bind these hydrogen atoms must be s/? 3-hybridized. Fig. 1. A three-dimensional m o d e l of t h e m e t h a n e m o l e c u l e . view of a Fig. 2. A t h r e e - d i m e n s i o n a l d r a w i n g of a m o d e l of e t h a n e . The feature which most distinguishes carbon from other elements is its ability to form strong covalent bonds to itself as well as to other elements.

10 shows space-filling models of several groups that commonly occur in organic compounds. The relative steric requirements of these groups should be noted. Fig. 10. Space-filling models of several common organic groups. ) CYCLOALKANES Let us imagine a simple " t h o u g h t " experiment. Two hydrogen atoms, one from each end, are removed from the hydrocarbon propane and a chemical bond is formed between the two terminal carbon atoms. A new hydrocarbon with the formula C 3 H 6 is thus formed. ) A similar experiment could be done with each of the normal (straight-chain) hydrocarbons to give corresponding new hydrocarbons with the general empiri­ cal formula C n H 2 n.

In contrast, cyclo­ hexene, though found only as the cis isomer, has essentially normal valence angles. The ring conformation of this latter cycloalkene bears little resemblance to the conformation of the corresponding cycloalkane. The preferred arrangement of the atoms of the cyclohexene ring is shown in Fig. 5. This arrangement is often called the envelope conformation. A "ring-flip" motion takes place in the cyclohexene ring, but this motion is more subtle than the ring flip in chaircyclohexane and occurs at a much higher rate.

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