CHE-234 Study Guide - Final Guide: Steric Effects, Dihedral Angle, Alkane Stereochemistry

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4 Apr 2021
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II. Nomenclature. IUPAC nomenclature of alkanes, branched alkanes, and cycloalkanes
and common names of branched substituents like isopropyl and tert-butyl.
III. Acid Base Chemistry
___ Arrhenius A/B theory.
___ Bronsted-Lowery A/B theory
a. The meaning of pKa, acid strength, anion stability.
b. Trends in anion stability
c. Determining which proton is most acidic.
d. Equilibria and the position of equilibria
e. Mechanism
___ Lewis A/B theory
IV. Conformational analysis
____ Linear and branched alkanes
a. Ethane
b. Propane
c. Butane
d. Other linear and branched alkanes
____ Important concepts regarding conformational analyses. . .
a. Newmann Projection
b. Eclipsed
c. Equatorial
d. Gauche
e. Anti- or anti-coplanar or anti-periplanar
f. Tortional strain
g. Steric hindrance
h. Dihedral angle
i. Electron pair repulsion
j. Potential energy vs. rotation diagrams
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IV. (Continued. . .)
____ Cycloalkanes
a. Cyclopropane
b. Cyclobutane (pucker)
c. Cyclopentane (envelope)
d. Cyclohexane (chair, axial, equatorial)
e. Angle strain and tortional strain (ring strain) of cycloalkanes.
f. Heats of combustion.
V. Stereochemistry
____ Isomerism
a. Isomers
b. Constitutional Isomers
c. Stereoisomers
1. Enantiomers
2. Diasteriomers
____ Nomenclature
a. cis-/trans-
b. E-/Z- (Cahn-Ingold-Prelog System for Assigning Priorities)
c. R-/S- (Cahn-Ingold-Prelog System for Assigning Priorities)
____ Chirality
a. Is it chiral or achiral
b. Chirality Centers
c. Plane of Symmetry
VI. Miscellaneous stuff
a. Energy/Reaction coordinate diagrams ('E as a function of a reaction progress,
rotation, or cyclohexane ring flip)
b. Exo/Endothermicity
c. Keq
d. Combustion analysis
e. Fischer projections
f. Optical activity
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VII. Substitution Reactions
____ SN2 reactions
a. Common structural features of substrates for SN2 reactions
b. Common nucleophiles
c. The mechanism
d. Stereochemical outcome of SN2 reactions
e. Thermodynamics of SN2 Reactions
f. Kinetics and the affect substrate and nucleophile strength has on reaction rates
____ SN1 reactions
a. Common structural features of substrates for SN1 reactions
b. Cation stability (hyperconjugation and resonance)
c. Common nucleophiles/solvents
d. The mechanism
e. Stereochemical outcome of SN1 reactions
f. Thermodynamics of SN1 Reactions
g. Kinetics and the affect substrate/cation stability has on reaction rates
h. Cation rearrangements
VIII. Elimination Reactions
____ E2 reactions
a. Common structural features of substrates for E2 reactions
b. Common bases
c. Influence of base size
d. Substitution pattern as it pertains to alkene stability (i. e. tetrasubstituted (more
stable) > trisubstituted > disubstituted > monosubstituted)
e. The mechanism
f. Kinetics
g. Anti-coplanarity of E-hydrogen and leaving group
____ E1 reactions
a. These reactions are most common with secondary and tertiary alcohols in the
presence of sulfuric acid or phosphoric acid. (i. e. the catalytic dehydration of
alcohols; see Klein for details).
b. The mechanism
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