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18 Cards in this Set

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How would you describe the pie bonds in benzene?
Delocalized - no longer localized in specific double bonds between two particular carbon atoms. They are spread out over all six atoms.
What is it called when two cdouble bonds are separated by just one single bond?
The two bonds are said to be ocnjugated.
In order to have a conjugated system, do the double bonds have to be with carbons?
No; the C=C and the C=O are conjugated in propenal, for example.
In propane, which carbon(s) would a nucleophile most likely attack?
The end carbons, because most electron density is on the central carbon, which means the end carbons are more positively charged.
If a single electron is left from a bond breaking homolytically, what type of orbital can it be found in?
The single electron would be in a p-orbital, because the carbon atom becomes trigonal, (sp^2), hybridized. The single electron in the p-orbital could overlap and combine with the pie bond.
Show the delocalization of the carboxylate anion.
B-13
Show the delocalizaton of the amide group.
B-14
As compounds become more conjugated, does the energy transition between HOMO and LUMO become greater or smaller?
Smaller
As compounds become more conjugated, the energy transition between HOMO and LUMO becomes greater. Therefore, can it absorb light with a longer or shorter wavelength?
Longer wavelength, which carries less energy
If the conjugation of a compound is extended far enough, why does it become colored?
The gap between HOMO and LUMO becomes sufficiently decreased to allow the comound to absorb visible light and, hence, be colored.
What is process called by which a double bond is converted to a single bond due to the addition of H?
Reduction
What is the stabilization called that allows aromatics to adopt planar structure, despite the strain of being planar?
The extra stabilization is called aromaticity.
What is hydrogenation?
The process by which unsaturated C=C double bonds are reduced using hydrogen gas and a catalyst, (usually nickel or palladium), to produce fully saturated alkanes.
What are molecular orbitals considered degenerate?
When different molecular orbitasl have exactly the same energy.
What are annulenes?
Compounds with alternating doulbe and single bonds.
What is Huckel's Rule?
PLanar, fully-conjugated, monocyclic systems with (4n+2)pie electrons have a closed shell of electrons all in bonding orbitals and are exceptionally stable. Such systems are said to be aromatic.
Analogous systems with 4npie electrons are described as anti-aromatic.
In terms of trans and cis, what conformation do annulenes take on?
Trans-trans-cis
Most aromatic systems are heterocyclic. What does this mean?
Heterocyclic means they involve atoms other than carbon and hydrogen.
(A carbon is replaced by a heteroatom within the ring, as in pyridine.)