Organic Chemistry

Bonding and Molecular Representations

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity with Mechanisms

Nucleophilic Substitution and Elimination

Alkenes and Alkynes

Radicals

Alcohols and Phenols

Ethers, Epoxides, Thiols, and Sulfides

Aldehydes and Ketones

Amines

Structural Theory, Lewis Structures, and Formal Charges

Hybridization, VSEPR Theory, Molecular Polarity, and Intermolecular Forces

Molecular Representations, Bond-Line Structures, and Functional Groups

Carbon Atoms with Formal Charges, Identifying Lone Pairs, Intro to Resonance, Curved Arrows

Alkane Nomenclature, Alkane Isomers, Newman Projections

Conformations

Chirality, Enantiomers, Cahn-Ingold-Prelog System, Optical Activity

Diastereomers, Symmetry, Fischer Projections, Enantiomeric Resolution, E/Z Designations

Enthalpy, Entropy, Free Energy, Equilibria, Kinetics, Energy Diagrams

Nucleophiles, Electrophiles, Mechanisms, Arrow Pushing

Substitution And Elimination Reactions, Alkyl Halides, SN2 Reactions

E2 Reactions, Alkenes

SN1 and E1 Reactions

Addition Reactions, Hydrohalogenation, Acid-Catalyzed Hydration

Catalytic Hydrogenation, Halogenation, Halohydrin Formation, Dihydroxylation, Oxidative Cleavage 

Naming Alkynes, Preparation of Alkynes, Reduction of Alkynes

Hydroghalogenation, Hydration, Halogenation, Ozonolysis, Alkylation

Radical Mechanisms, Chlorination of Methane, Selectivity of Halogenation

Halogenation Stereochemistry, Allylic Bromination, Atmospheric Chemistry, Radical Addition

Alcohols, Acidity of Alcohols & Phenols, Preparation of Alcohols

Grignard Reagents, Alcohol Reactions

Naming Ethers, Properties of Ethers, Preparation and Rxns of Ethers

Naming Epoxides, Preparation of Epoxides, Sulfides and Thiols

Naming Aldehydes & Ketones, Nucleophilic Addition Reactions

Nucleophiles, Hydrolysis, Oxidation

Naming Amines, Properties of Amines, Preparation of Amines, Substitution and Reductive Amination

Amine Acylation, Hofmann Elimination, Amine Reactions

I can draw constitutional isomers.

I can draw Lewis structures.

I can determine formal charges.

I can determine the polarity of a bond.

I can write electron configurations for elements.

I can determine the hybridization of an element in a compound.

I can determine the shape of a molecule.

I can determine the polarity of a molecule.

I can identify the intermolecular forces within a molecule.

I can draw Lewis structures for condensed structures.

I can draw bond-line structures for compounds.

I can identify functional groups within a molecule.

I can identify the lone pairs on oxygen and nitrogen atoms in Lewis structures.

I can draw curved arrows correctly in Lewis structures.

I can draw resonance structures as indicated by curved arrows.

I can draw all significant resonance forms and rank them from most significant to least significant.

I can draw the resonance hybrid for a molecule.

I can determine the localized and delocalized lone pairs in a molecule.

I can name alkanes and cycloalkanes.

I can identify constitutional isomers of alkanes.

I can draw Newman projections of alkanes.

I can draw conformations of an alkane.

I can identify the highest and lowest energy conformations of an alkane.

I can draw chair conformations of cyclohexanes.

I can draw Haworth projections for cis- and trans- isomers.

I can identify chiral centers in compounds.

I can draw the enantiomers of a compound.

I can determine the S,R configuration of a compound.

I can calculate the specific rotation of a compound.

I can calculate the percent enantiomeric excess of a compound.

I can differentiate between enantiomers and diastereomers.

I can identify the plane of symmetry of a molecule.

I can draw and interpret Fischer projections.

I can assign E or Z designations to alkenes.

I can calculate the enthalpy of a reaction.

I can determine an increase or decrease in the entropy of a reaction.

I can determine the spontaneity of a reaction. 

I can interpret an energy diagram.

I can identify nucleophile or electrophile centers in a molecule.

I can identify arrow-pushing patterns in ionic mechanisms.

I can draw curved arrows in ionic mechanisms.

I can name compounds containing an alkyl halide.

I can draw the products of a SN2 reaction.

I can draw the transition state of a SN2 reaction.

I can explain the effects of substituents and solvents on SN2 reactions.

I can name alkenes.

I can determine the stability of isomeric alkenes.

I can predict the major and minor products of E2 reactions.

I can draw the structure of the carbocation intermediate of a SN1 or E1 reaction.

I can draw the products of a SN1 or E1 reaction.

I can draw the major product of an addition reaction. 

I can draw a mechanism for a hydrohalogenation reaction.

I can draw a mechanism for a hydrohalogenation reaction with a carbocation rearrangement.

I can draw a mechanism for an acid-catalyzed hydration reaction.

I can predict the products of a catalytic hydrogenation reaction. 

I can predict the products of a halogenation reaction.

I can predict the products of a halohydrin formation reaction.

I can predict the products of a dihydroxylation reaction.

I can predict the products of an ozonolysis reaction.

I can name alkynes.

I can draw the major product and draw the mechanism for the formation of alkynes.

I can draw the major product of a hydrogenation reaction involving alkynes.

I can draw the major product of the dissolving metal reduction of alkynes.

I can predict the products of an alkyne hydrohalogenation reaction.

I can predict the products of an alkyne hydration reaction.

I can predict the major product of an alkyne halogenation reaction.

I can predict the major products of the ozonolysis of an alkyne.

I can determine the reagents needed to convert acetylene into various alkylated alkynes.

I can determine the stability of a radical.

I can draw resonance structures for radicals. 

I can draw appropriate fishhook arrows for radical processes.

I can draw mechanisms for radical fluorination, chlorination, and bromination. 

I can predict the major product of radical fluorination, chlorination, and bromination.

I can predict the stereochemical outcome of radical bromination.

I can predict the products of allylic bromination.

I can predict the products of radical addition of HBr.

I can name alcohols. 

I can draw an alkoxide ion when an acid is deprotonated.

I can determine the relative strength of an acid.

I can determine the reagents needed to convert alkenes and halogenoalkanes into alcohols.

I can determine what is oxidized or reduced during reductive alcohol preparation.

I can draw the mechanism of a reductive alcohol preparation.

I can predict the major product of a reductive alcohol preparation.

I can show how to use a Grignard reagent to prepare an alcohol.

I can identify the reagents required to transform alcohols during halogenation.

I can predict the products of alcohol substitution and elimination reactions.

I can predict the products of alcohol oxidation reactions.

I can name compounds containing ether functional groups. 

I can identify the crown ether needed to perform substitution reactions.

I can identify the reagents needed to perform a Williamson ether synthesis.

I can predict the products of an acidic cleavage reaction.

I can name epoxides.

I can identify reagents required to produce epoxides.

I can predict the products and draw a mechanism for ring-opening epoxide reactions.

I can predict the products of thiol and sulfide reactions.

I can name aldehydes and ketones.

I can identify reagents needed to prepare aldehydes and ketones.

I can draw mechanisms for nucleophilic addition reactions.

I can predict the products of aldehyde and ketone nucleophilic addition reactions.

I can predict the products of hydrolysis reactions involving acetals, imines, and enamines.

I can predict the product of Baeyer-Villiger oxidation reactions.

I can name amines. 

I can correlate the structure of amines to basicity.

I can use a Gabriel synthesis to prepare amines.

I can use reductive amination to prepare amines.

I can describe the acylation of an amine.

I can predict the product of a Hofmann elimination.

I can predict the product of the reaction between an amine and nitrous acid.

I can propose a synthesis for a Sandmeyer or Schiemann reaction.

I can identify the reactants needed to produce an azo dye via an azo coupling reaction.