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14 • Summary

14 • Summary

The unsaturated compounds we’ve looked at previously have had only one double bond, but many compounds have numerous sites of unsaturation, which gives them some distinctive properties. Many such compounds are common in nature, including pigments and hormones.

A conjugated diene or other compound is one that contains alternating double and single bonds. One characteristic of conjugated dienes is that they are more stable than their nonconjugated counterparts. This stability can be explained by a molecular orbital description in which four p atomic orbitals combine to form four π molecular orbitals. Only the two bonding orbitals are occupied; the two antibonding orbitals are unoccupied. A π bonding interaction in the lowest-energy MO introduces some partial double-bond character between carbons 2 and 3, thereby strengthening the C2–C3 bond and stabilizing the molecule.

Conjugated dienes undergo several reactions not observed for nonconjugated dienes. One is the 1,4-addition of electrophiles. When a conjugated diene is treated with an electrophile such as HCl, 1,2- and 1,4-addition products are formed. Both result from the same resonance-stabilized allylic carbocation intermediate and are produced in varying amounts depending on the reaction conditions. The 1,2 adduct is usually formed faster and is said to be the product of kinetic control. The 1,4 adduct is usually more stable and is said to be the product of thermodynamic control.

Another reaction unique to conjugated dienes is Diels–Alder cycloaddition. Conjugated dienes react with electron-poor alkenes (dienophiles) in a single step through a cyclic transition state to yield a cyclohexene product. The reaction is stereospecific, meaning that only a single product stereoisomer is formed, and can occur only if the diene is able to adopt an s-cis conformation.

Ultraviolet (UV) spectroscopy is a method of structure determination applicable specifically to conjugated π-electron systems. When a conjugated molecule is irradiated with ultraviolet light, energy absorption occurs and a π electron is promoted from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO). For 1,3-butadiene, radiation of λmax = 217 nm is required. The greater the extent of conjugation, the less the energy needed and the longer the wavelength of radiation required.

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