By J.T. Gerig (Auth.)
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Extra resources for Introductory Organic Chemistry
54 Alkenes Fig. 1. 55 B o n d i n g in t h e e t h y l e n e m o l e c u l e . This second carbon-carbon bond is fundamentally different from the first bond which joined the two carbon atoms. The first bond was fashioned by the end-on overlap of two atomic orbitals; bonds created in this way are called σ (sigma) bonds. The second bond, called a π (pi) bond, was constructed by overlapping ρ orbitals in a sideways manner so that there were two points of contact between the atomic orbitals. The electrons in this second carbon-carbon bond tend to be distributed over a larger volume than those of the σ bond.
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. Such molecules exist and are said to be cyclic hydrocarbons or cycloalkanes because the carbon backbone of the molecules defines a ring Cycloalkanes Propane 39 Cyclopropane structure, rather than a chain.
In case two groups are attached to the double bond through the same kind of atom, then the next atom removed from the double bond is used in determining the priority ranking of the substituent. If the two groups of highest priority at each end of the double bond are on the same side, the isomer is designated as Ζ (from the German word zusammen, together). If these two groups are on opposite sides of the double bond, the isomer is called Ε (from the German word entgegen, opposite). T h e first molecule shown above is thus (£)-l,2-dichloro-l-fluoroethylene, while the other is the Z-isomer.