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Organic Chemistry Exam 2 Topics

Know how to draw molecules from molecular formula


Functional Groups
General Formula for Alkanes = CnH2n+2
Saturated vs Unsaturated Carbons
General Formula for Cycloalkanes = CnH2n
IUPAC nomenclature / Rules for Alkanes & Cycloalkanes
Common names for Substituents (Isopropyl, t-Butyl, Isobutyl, Sec-butyl,
etc)
What causes increase/decrease in Boiling Point
o Be able to indicate which has lowest vs highest boiling point
Newman Projections
Staggered vs Eclipsed Formations
o Fully eclipsed, Staggered-Gauche, Eclipsed, Staggered-Anti
o Energy Diagram for each formation
Rank each of the formation from least to greatest energy or
greatest to least energy
Chair Configuration
o Explain why Chair form takes place
o Energy diagram for chair and boat formation
Axial Up, Axial Down, Equatorial Up and Equatorial Down
Stability for equatorial position know what causes interaction and
what does not
Stereochemistry
Cis/Trans Isomers
Flipping Chair (Ring Flip) Configurations
o Be able to recognize which conformation is more stable
Change in energy due to ring flip (Go) look at a practice problem
o Draw two conformations of a molecule, estimate the energy
differences between the two, identify which is most stable of the
two conformers
o See in a solution, what % of each of the conformation should be
present.
Change from Newman Projections to Chair Projections and Vice-Versa
Rank substituents from order of priority
Chirality Centers
R configurations and S configurations
Chiral vs Achiral, Achiral Meso, Chiral R/S
Differentiate between Enantiomers, Stereoisomers, Diastereomers,
Constitutional Isomers, Meso Compounds or Same Molecules
Hybridization of each atom within a molecule

% ee calculation of R & S
Specific rotation problems look at practice problems
Fisher Projections
Differentiate between enantiomers, diastereomers and mesocompounds while comparing Fisher projections
Be sure to fully label a molecule with its full IUPAC name; draw a
molecule with its full IUPAC name
Label stereo centers/chirality centers properly as R/S
Reactions H2 + Catalyst
Stability based on carbocation location
Carbocation rearrangement
Atropisomers are stereoisomers arising because of hindered rotation
about a single bond, where energy differences due to steric strain or
other contributors create a barrier to rotation that is high enough to
allow for isolation of individual conformers.

Optical activity in polarized light


Cahn-Ingold-Prelog stereochemical designations
Electrophile (Lewis Acid) and Nucleophile (Lewis Base)
o Identify which is which in a given reaction
Be able to show the movement of electrons
Know which reactions would have the most negative S (change in
entropy)
Reactions with the most amount of exothermic heat of reaction Ho
Estimating enthalpy change of reactions under standard conditions
Proton Transfer, Loss of Leaving Group, Nucleophilic Attack,
Rearrangement