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Spectroscopy
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Order
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Description
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1
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Interpret mass spectrometry of small molecules, common functional groups and biological molecules.
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2
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Compare and contrast infrared spectra.
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3
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Evaluate nuclear magnetic resonance spectroscopy.
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4
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Interpret 13C NMR spectroscopy including: signal averaging, FT-NMR and DEPT.
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5
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Make sense of 1H NMR spectroscopy utilizing proton equivalence, chemical shifts, integration and spin-spin coupling.
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6
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Interpret 1H NMR spectra.
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7
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Interpret ultraviolet spectra and the effect of conjugation.
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Aromaticity
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Order
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Description
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1
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Examine sources and names of aromatic compounds, the structure and stability of benzene, aromaticity and the Huckel 4n + 2 rule, and aromatic ions.
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2
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Evaluate aromaticity heterocycles, polycyclic aromatics and the spectroscopy of aromatic compounds.
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3
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Compare and contrast electrophilic aromatic substitution reactions including bromination, Friedel-Crafts alkylation and acylation reactions and other aromatic substitutions.
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4
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Interpret substituent effects in substituted aromatic rings.
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5
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Examine nucleophilic aromatic substitution and benzyne.
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6
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Compare and contrast oxidation and reduction of aromatic compounds.
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7
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Evaluate synthesis of trisubstituted benzenes.
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Alcohols, phenols, ethers, epoxides, thiols and sulfides
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Order
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Description
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1
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Examine naming and properties of alcohols and phenols.
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2
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Interpret reactions for the preparation of alcohols from reduction of carbonyl compounds and reaction of carbonyls with Grignard reagents.
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3
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Evaluate reactions, oxidations and protection of alcohols.
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4
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Assess phenols: their uses and reactions.
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5
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Interpret spectroscopy of alcohols and phenols.
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6
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Examine naming properties and synthesis of ethers.
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7
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Examine reactions of ethers: acidic cleavage and Claisen rearrangement.
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8
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Evaluate epoxides, ring-opening reactions of epoxides and crown ethers.
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9
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Evaluate thiols and sulfides.
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10
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Interpret spectroscopy of ethers.
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Aldehydes, ketones, carboxylic acids and nitriles
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Order
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Description
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1
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Compare kinds of carbonyl compounds, nature of carbonyl and general reactions of carbonyl compounds.
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2
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Examine naming aldehydes and ketones, preparation of aldehydes and ketones, oxidation of aldehydes and ketones.
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3
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Evaluate nucleophilic addition reactions of aldehydes and ketones: hydration, cyanohydrin formation, Grignard and hydride reagents, imine and enamine formation, Wolff-Kishner reduction, acetal formation and Wittig reaction.
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4
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Examine biological reductions and conjugate nucleophilic addition to (alpha, beta)-unsaturated aldehydes and ketones.
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5
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Interpret spectroscopy of aldehydes and ketones.
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6
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Examine naming, structure and properties of carboxylic acids and nitriles.
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7
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Examine biological acids and the Henderson-Hasselbalch equation.
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8
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Evaluate substituent effects on acidity and the preparation of carboxylic acids, reactions of carboxylic acids and the chemistry of nitriles.
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9
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Interpret spectroscopy of carboxylic acids and nitriles.
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Carboxylic acid derivatives
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Order
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Description
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1
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Examine naming of carboxylic acid derivatives and nucleophilic acyl substitution reactions.
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2
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Evaluate the chemistry of acid halides, acid anhydrides, esters, amides, thioesters and acyl phosphates (biological carboxylic acid derivatives).
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3
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Examine examine polyamides and polyesters - step-growth polymers.
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4
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Interpret spectroscopy of carboxylic acid derivatives.
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5
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Characterize keto-enol tautomerism and the reactivity of enols (mechanism of alpha-substitution).
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6
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Evaluate alpha halogenation of aldehydes and ketones and the bromination of carboxylic acids (Hell-Volhard-Zelinskii reaction).
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7
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Examine enolate ions: acidity of alpha hydrogen atoms, reactivity and alkylation.
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8
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Compare and contrast carbonyl condensation versus alpha substitution.
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9
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Evaluate carbonyl condensations: aldol reactions, dehydration of aldol products (synthesis of enones), aldol reactions in synthesis, mixed aldol reactions and intramolecular aldol reactions.
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10
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Evaluate Claisen condensations, mixed Claisen condensations, intramolecular Claisen
condensations (Dieckmann cyclization), conjugate carbonyl additions (Michael reaction), carbonyl condensations with enemines (Stork reaction), Robinson annulation reaction and some biological carbonyl condensation reactions.
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Amines, heterocycles and carbohydrates
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Order
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Description
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1
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Examine naming amines, properties of amines, basicity of amines and substituted arylamines, biological amines and the Henderson-Hasselbalch equation.
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2
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Evaluate synthesis of amines, reactions of amines, reactions of arylamines and heterocycles.
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3
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Interpret spectroscopy of amines.
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4
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Examine classification of carbohydrates, depict carbohydrate stereochemistry (Fisher projections), D, L sugars and configuration of the aldoses.
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5
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Evaluate cyclic structures of monosaccharides (anomers), reactions of monosaccharides and essential monosaccharides.
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6
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Examine disaccharides, polysaccharides and their synthesis, other important carbohydrates, cell-surface carbohydrates and carbohydrate vaccines.
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