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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,
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
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
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
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,