nodal planes for each molecular orbital. Hint: A nodal plane is a line through the molecule that denotes the sites of destructive interference. An example is shown below with ethylene. b) Based on the nodal planes, arrange the energy levels corresponding to the 8 molecular orbitals on the energy level diagram (label them using the numbering provided on the left side of the molecular orbitals) on the next page, in order of lowest to highest energy. c) Populate your molecular orbitals with electrons according to the filling rules given in the class and label both the HOMO and the LUMO on your energy level diagram
Basics in Organic Reactions Mechanisms
In organic chemistry, the mechanism of an organic reaction is defined as a complete step-by-step explanation of how a reaction of organic compounds happens. A completely detailed mechanism would relate the first structure of the reactants with the last structure of the products and would represent changes in structure and energy all through the reaction step.
Heterolytic Bond Breaking
Heterolytic bond breaking is also known as heterolysis or heterolytic fission or ionic fission. It is defined as breaking of a covalent bond between two different atoms in which one atom gains both of the shared pair of electrons. The atom that gains both electrons is more electronegative than the other atom in covalent bond. The energy needed for heterolytic fission is called as heterolytic bond dissociation energy.
Polar Aprotic Solvent
Solvents that are chemically polar in nature and are not capable of hydrogen bonding (implying that a hydrogen atom directly linked with an electronegative atom is not found) are referred to as polar aprotic solvents. Some commonly used polar aprotic solvents are acetone, DMF, acetonitrile, DMSO, etc.
Oxygen Nucleophiles
Oxygen being an electron rich species with a lone pair electron, can act as a good nucleophile. Typically, oxygen nucleophiles can be found in these compounds- water, hydroxides and alcohols.
Carbon Nucleophiles
We are aware that carbon belongs to group IV and hence does not possess any lone pair of electrons. Implying that neutral carbon is not a nucleophile then how is carbon going to be nucleophilic? The answer to this is that when a carbon atom is attached to a metal (can be seen in the case of organometallic compounds), the metal atom develops a partial positive charge and carbon develops a partial negative charge, hence making carbon nucleophilic.
- 4. Octatetraene, C8H10, is an 8-membered linear carbon chain with alternating single and double
bonds. As a result, each carbon is left with an unhybridized p-orbital containing one electron.
This problem will take you through steps to construct and fill the molecular orbital diagram for
octatetraene based on the way these different p-orbitals can come together.
a) The various molecular orbitals formed from octatetraene’s 8 unhybridized p-orbitals are
shown on the next page. Draw the nodal planes for each molecular orbital.
Hint: A nodal plane is a line through the molecule that denotes the sites of destructive
interference. An example is shown below with ethylene.
b) Based on the nodal planes, arrange the energy levels corresponding to the 8 molecular
orbitals on the energy level diagram (label them using the numbering provided on the left
side of the molecular orbitals) on the next page, in order of lowest to highest energy.
c) Populate your molecular orbitals with electrons according to the filling rules given in the class
and label both the HOMO and the LUMO on your energy level diagram.
d) Based on the diagram, what is the bond order of the ions C8H10+ and C8H102- ? Are these ions
paramagnetic or diamagnetic?
Electrons first filled the space at lower energy levels then upper energy levels in chronological order .
HOMO = Highest occupied molecular orbital
LUMO = Lowest unoccupied molecular orbital
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