Course Objectives

• Know the language and grammar of Organic Chemistry.
  • Draw organic molecules with appropriate electrons and charges.
  • Name organic molecules
  • Classify organic molecules by functional group
  • Represent and recognize three-dimensional shapes on paper...
    • using the wedge-dash formalism
    • using Newman projections
    • for different conformations of cyclohexanes
  • Classify any two molecules as being...
    • identical or different
    • constitutional isomers or stereoisomers
    • enantiomers or diastereomers
  • Represent reactions and reaction mechanisms using the appropriate arrow formalisms.
• Analyze the stability of organic molecules using ...
  • bond strengths
  • electronegativities
  • resonance theory
  • molecular orbital theory
  • analysis of electronic and steric interactions
• Evaluate molecular reactivity.
  • Predict products based on reactants (and vice versa).
  • Use molecular orbital theory, resonance theory, and reaction coordinate diagrams, and mechanisms to understand reactivity patterns.
• Apply the mechanism of reactivity to ...
  • compose a reaction coordinate diagram
  • predict reaction selectivity
  • explain new results
• Compose the synthesis of an organic molecule by ...
  • using the retrosynthetic method
  • assembling learned reactions
  • evaluating multiple pathways

Chapter 1: Electronic Structure, Bonding, Acids/Bases

Objectives

• List the energetic ordering of atomic orbitals in H-Ar.
• Know the rules for the construction and filling of molecular orbitals.
• Know the use and limitations of Lewis structures (including formal charges).
• Be able to distinguish resonance from equilibrium.
• Recognize electronegativity and its implications for polar bonds.
• Apply your knowledge of shape and electronegativity to the determination of dipole moments (molecular polarity).
• Understand and utilize the different kinds of arrows properly.
• Identify acids, bases, conjugate bases, and conjugate acids.
• Be able to use pKa to determine acid and base strength and Keq for any acid/base reaction.

Skill-building Problems: in-chapter + 68-70, 73-87

Quiz-like Problems: 84, 88, 90-93, 95-97

X Topics: Molecular Orbital Theory, Functional Groups, Ways of Drawing Molecules, Evaluating Resonance Forms, and Ranking Acids and Bases.

Objectives

• Know the rules for the construction and filling of molecular orbitals.
• Understand covalent bonding in terms of orbital overlap, bonding, and antibonding orbitals.
• Be able to quickly identify atoms by their hybridization and recognize the energetic and molecular shape consequences of hybridization.
• Be able to calculate bond order.
• Be able to draw organic molecules using Lewis structures, skeletal structures, condensed formulas, or perspective formulas.
• Be able to identify functional groups based on IUPAC names.
• Recognize and characterize all of the important functional groups by their chemical structure.
• Be able to draw all reasonable resonance forms.
• Be able to rank the reasonableness of resonance forms.
• Utilize charge, size, electronegativity, resonance theory, the inductive effect, and hybridization to predict stability of acids and bases.
• Acid/Base Reactions:
  • Rationalize the pKa's of common functional groups
  • Rank acids from strongest to weakest.
  • Rank bases from strongest to weakest.

Reading/Problems: orbital tutorial, important functional groups (Bruice back inside cover and here), drawing molecules (Bruice p. 72 & 82), evaluating resonance (Bruice pp. 291-300), Ranking Acids/Bases (Bruice pp. 51-60).

Chapter 2: Introduction to Organic Compounds

Objectives

• Find all of the constitutional isomers of a given formula.
• Name alkanes, cycloalkanes, alcohols, amines, alkyl halides, and ethers using IUPAC nomenclature.
• Name ethers and amines using common names.
• Be able to identify molecules and atoms by as primary, secondary, tertiary, or quaternary.
• Draw structures for any of these names.
• Rank molecules by boiling point and water solubility.
• Recognize, represent, and rank the stability of molecules in 3D using
  • the wedge-dash formalism
  • Newman projections
  • Chair conformations of cyclohexane (beautifully drawn).
  • names like "eclipsed," "staggered," "anti," and "gauche."
• Know how to represent cyclohexane conformations on paper with distinct axial and equatorial substituents.
• Know how to evaluate the stability of various conformations of substituted cyclohexanes based on
  • eclipsing interactions
  • gauche interactions ("1,3-diaxial strain")
  • and other steric interactions
• Recognize ring strain as a significant destabilization in small rings.
• Understand the origins of ring strain in terms of
  • angle strain (poor orbital overlap)
  • and eclipsing strain

Skill-building Problems: in-chapter + 45, 47-51, 53, 55, 57, 59-71, 73

Quiz-like Problems: 46, 52, 54, 56, 58, 61, 66, 69, 72

Chapter 3: Alkenes

Objectives

• Calculate index of hydrogen deficiency (aka, IHD, degrees of unsaturation, or Ω)
• Understand the difference between σ and π bonding
  • in terms of bond strengths
  • in terms of orbital overlap
• Recognize stereoisomerism in alkenes and the implication for IUPAC naming (cis/trans, E/Z).
• Use IUPAC nomenclature to name alkenes.
• Draw alkenes from their IUPAC names.
• Draw mechanisms with proper arrows and balancing.
• Identify electrophiles and nucleophiles.
• Understand kinetic and thermodynamic control of reaction outcomes.
• Understand how reaction coordinate diagrams relate to kinetic/thermodynamic control and mechanism.

Skill-building Problems: in-chapter + 34-36, 38-46, 49, 53, 54

Quiz-like Problems: 37, 47, 48, 50

Chapter 4: Reactions of Alkenes

Objectives

• Recognize and classify alkene addition reactions.
• Recall and explain the relative stability of carbocations.
• Use mechanisms to explain regioselectivity of alkene additions.
• Identify the products and mechanisms resulting from carbocation rearangements.
• Use Markovnikov's rule to plan alkene addition syntheses.
• Use the Hammond Postulate to predict the structure, charge, and energy of transition states.
• Know the mechanism, products, reactants, and use in synthesis of the following alkene reactions:
  • hydrohalogenation
  • hydration
  • alcohol addition
  • halogenation
  • halohydrin formation
  • oxymercuration-reduction
  • epoxidation
  • hydroboration-oxidation
  • hydrogenation
• Recognize the relative stability of alkenes based on substitution patterns.

Skill-building Problems: in-chapter + 37, 38, 42, 45, 47, 49, 50, 52, 57

Quiz-like Problems: 39, 41, 43, 44, 46, 48, 51, 54, 55, 60, 61

Chapter 5: Stereochemistry

Objectives

• Find all isomers of a given formula (including stereoisomers) and characterize any two structures as constitutional isomers, enantiomers, or diastereomers.
• Recognize chiral molecules, labeling their asymmetric centers or stereogenic centers.
• Be able to quickly predict the maximum number of stereoisomers possible for a given structure.
• Name and draw chiral molecules appropriately, without being prompted.
• Understand the effect of stereochemistry on physical properties, chemical reactivity, and optical activity.
• Apply and interpret the terms chiral, achiral, meso, optically active, optically inactive, and racemic.
• Recognize and apply the stereochemical consequences of reaction mechanisms.

Skill-building Problems: in-chapter + 58-62, 65-68, 71, 72, 75, 76, 79, 82, 91, 94-96

Quiz-like Problems: 63, 64, 70, 73, 77, 78, 80, 83, 87-89, 92

Chapter 6: Reactions of Alkynes

Objectives

• Use IUPAC nomenclature to name alkynes.
• Draw alkynes from their IUPAC names.
• Name molecules with more than one functional group.
• Understand the bonding, physical properties, and acidity of alkynes.
• Recognize the similarities and differences for addition reactions of alkynes viz-a-viz alkenes.
• Know the mechanism*, regiochemistry, stereochemistry, products, reactants, and use in synthesis of the following alkyne reactions:
• • hydrohalogenation*
  • halogenation
  • hydrogenation
  • hydration* (inc. mercury catalyzed)
  • hydroboration*-oxidation
  • hydrogenation with Lindlar's catalyst
  • conversion to trans-alkenes*
  • deprotonation/alkylation*
• Use a retrosynthetic analysis to design a multi-step synthesis.

Skill-building Problems: in-chapter + 24-29, 32-33, 35, 37, 38, 40, 42, 43, 45-47

Quiz-like Problems: 30, 31, 34, 36, 39, 41, 44, 49, 50

Chapter 7: Delocalized Electrons & MO Theory: Stability, Reactivity, pKa

Objectives

• Draw all of the reasonable resonance contributors for a molecule and rank them based on importance.
• Identify conjugated systems and the stability associated with resonance, conjugation, and aromaticity.
• Draw and analyze the p-MO diagram of any conjugated molecule with the proper phase drawings, energy orderings, and electron fillings.
• Use these drawings to evaluate stability.
• Identify the HOMO and LUMO for an MO and recognize the consequences for reactivity.
• Recognize the role of resonance and conjugation in the mechanism of chemical reactions.
• Understand and utilize kinetic or thermodynamic control of reaction mixtures.
• Know the mechanism, stereochemistry, products, reactants, and use in synthesis of the Diels-Alder reaction.

Skill-building Problems: in-chapter + 40, 45, 46, 48, 49, 52, 54-56, 58, 69-71

Quiz-like Problems: 41, 42, 44, 47, 50, 51, 53, 57, 59-63, 65-67, 72-75, 81

Preview: Substitution and Elimination

Objectives

• Be able to categorize a reaction as an addition, elimination, or substitution.
• Recognize such reactions not just with alkyl halides but all manner of organic reactants including alcohols, sulfonate esters, ethers, epoxides, etc.
• Be able to identify nucleophiles and electrophiles.
• Recognized that the difference between substitution and elimination is whether the reagent acts as a nucleophile or base.
• Be able to rank bases from strongest to weakest.
• Be able to rank nucleophiles from strongest to weakest.
• Classify solvents as polar or nonpolar and protic or aprotic.