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Structure and Bonding
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Order
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Description
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1
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Examine atomic structure, the nucleus, orbitals, and electron configuration.
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2
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Express valence bond theory.
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3
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Differentiate hybrid orbitals.
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4
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Express molecular orbital theory.
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5
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Examine chemical structures.
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6
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Evaluate polar covalent bonds and their electronegativity, dipole moments, formal charges, and resonance.
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7
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Differentiate acids and bases.
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Organic structure: alkanes, cycloalkanes and their stereochemistry
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Order
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Description
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1
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Compare functional groups.
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2
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Classify alkanes, isomers, and groups.
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3
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Examine nomenclature of alkanes and cycloalkanes.
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4
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Compare properties of alkanes and cycloalkanes.
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5
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Evaluate Cis-Trans isomerism in cycloalkanes.
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6
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Examine stability and conformations of cycloalkanes.
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7
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Differentiate axial and equatorial bonds in cycloalkanes.
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Overview of organic reactions
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Order
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Description
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1
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Compare types of reactions.
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2
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Differentiate mechanisms.
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3
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Predict reactions using equilibria, rates, energy changes, bond dissociation energies, energy diagrams, transition states, and intermediates.
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Alkenes, alkanes, and conjugated compounds: their structure, reactivity, and synthesis
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Order
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Description
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1
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Evaluate degrees of unsaturation and name alkenes including Cis-Trans and E-Z designations. Name alkynes.
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2
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Examine stability of alkenes.
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3
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Evaluate electrophilic addition reactions of alkenes including orientation, Markovnikov's rule, carbocation structure and stability, Hammond postulate, and rearrangement.
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4
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Examine preparations of alkenes and alkynes by elimination.
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5
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Evaluate reactions of alkenes including adding halogens, hypohalous acids, oxymercuration, hydroboration, carbine addition, hydrogenation, epoxidation, hydroxylation, cleavage to carbonyls, and radical additions.
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6
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Evaluate reactions of alkynes including addition of halides, hydrogen halides and water, reductions; oxidative cleavage; alkyne acidity; and alkylation of acetylide ions.
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7
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Design organic synthesis.
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8
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Examine stability of conjugated dienes using Molecular Orbital Theory.
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9
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Evaluate electrophylic additions to conjugated dienes to differentiate between kinetic and thermodynamic control.
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10
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Examine the Diels-Alder reaction and its characteristics.
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11
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Examine natural and synthetic diene polymers.
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Stereochemistry
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Order
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Description
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1
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Compare enantiomers at the tetrahedral carbon and examine chirality.
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2
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Evaluate optical activity including Pasteur's discovery of enantiomers and the sequence rules for specifying configuration.
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3
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Examine diastereomers, meso compounds, racemic mixtures, and the resolution of enantiomers.
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4
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Relate types of isomerism.
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5
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Examine reaction stereochemistry of addition of water to achiral and chiral alkenes.
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6
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Compare chirality at nitrogen, phosphorous, and sulfur.
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7
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Distinguish prochirality and analyze chirality in nature and chiral environments.
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Organahalides and their reactions
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Order
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Description
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1
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Examine nomenclature of alkyl halides and examine their structures.
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2
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Evaluate preparation of alkyl halides from alkanes (radical halogenation), alkenes (allylic bromination), and alcohols.
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3
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Examine the stability of allylic radicals.
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4
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Examine reactions of alkyl halides including Grignard reagents, organometallic coupling reactions, and oxidation/reduction concepts of organic chemistry.
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5
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Examine the discovery of nucleophilic substitution reactions.
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6
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Differentiate Sn1 and Sn2 reactions and their characteristics. Examine biological substitution reactions.
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7
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Examine elimination reactions of alkyl halides using Zaitsev's rule.
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8
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Evaluate the deuterium isotope effect and cyclohexane conformation on the E2 reaction.
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9
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Examine the E1 and E1cB reactions.
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10
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Examine biological elimination reactions.
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