General Organic Chemistry Links:

Bruice Textbook site: http://www.prenhall.com/bruice/ 
Lab Text Web Site:  http://bcs.whfreeman.com/mohrig/   

A virtual text online: http://www.cem.msu.edu/~reusch/VirtualText/intro1.htm
There are nice quizzes embedded in the various topics.

A. Atomic Structure
   1. the nucleus: atomic number, atomic mass, isotopes, atomic weight

   2. the electron cloud  "Quantum Mechanics"  Schrodinger's equation, orbitals, electron configurations, Aufbau Principle, Pauli Principle, Hund's Rule, degenerate orbitals, valence electrons,  Lewis Dot Structures

B. Bonding
   1. Atom instability, electronegativity, ionization energy, DEN, covalent, polar covalent bonds, non-polar covalent bonds, ionic bonds, measuring magnitude of charge in Debyes, bond length, dipole moment

   2. Covalent bonding theories: MO Theory, bonding e, antibonding e, electron configurations using MO, bond order, paramagnetism, diamagnetism, electron delocalization, VB Theory, VSEPR, atomic orbital hybridization sp3, sp2, sp, left over p-orbitals, sigma bonds, pi bonds, bond notation, bond geometry, electron delocalization and the drawing of resonance contributors, bond lengths, dipole moments

C. Acids and Bases
   1. Arrhenius, Bronsted-Lowry, Lewis definitions of acids and bases
    2. Keq vs. Ka, pKa, Henderson-Hasselbalch equation, ratio of deprotonated to protonated forms of a compound, buffer, acid and conjugate base strength as a function of pKa, using pKas to predict reactivity, using pKas to determine whether reactants or products are favored at equilibrium, using pKas to choose find the appropriate base for deprotonating an acid or find the appropriate acid for protonating a base.
   3. Structural factors that influence pKas, electronegativity, atom size, inductive electron withdrawal, inductive electron donation, resonance stabilization of the conjugate base.
 

A. Classes of Organic Compounds
1. Hydrocarbons: Alkanes, alkenes, alkynes, 2. Other Classes: alkyl halides, alcohols, ethers, aldehydes, ketones, carboxylic acids, esters, acid anhydrides, amines, amides, nitriles, thiols, thioethers, thioesters

B. Nomenclature
1. alkanes, 2. cycloalkanes, 3. alkyl halides, 4. alcohols, 5. ethers, 6. amines

Find summaries and practice here: http://www.chem.ucalgary.ca/courses/351/Carey/nomenclature/index.html

C. Physical Property Trends
intermolecular forces: 1. boiling point trends of alkanes, alkyl halides, ethers, alcohols, and amines, melting point trends of alkanes,  2. solubility in H₂O of alkanes (cycloalkanes are included), alkyl halides, alcohols, ethers, amines

D. Structural Conformations
1. Bond Rotation: s bonds vs. p bonds; representations of ethane: perspective drawings, sawhorse, and Newman projections, staggered vs. eclipsed conformations, dihedral angle, torsional strain = steric strain, hyperconjugation;
Newman projection of propane; Newman projection of butane: 3 staggered conformers, 1 anti + 2 gauche. 3 eclipsed conformers, 1 "syn" and 2 that shall remain nameless; Newman projections: from skeletal structures and names and vice versa.

2. Cycloalkane  conformations: a) cyclopropane:  banana bonds, angle strain b) cyclobutane: puckering c) cyclopentane, envelope d) cyclohexane: chair conformations, axial vs. equatorial positions, Newman projection of chair, ring flip, boat conformation, flagpole Hs, e) relative stability of both chairs of monosubstituted cyclohexanes,1,3-diaxial interactions f) disubstituted cyclohexanes: trans vs. cis isomers (include in naming and make clear in drawings.

Here's a website that might provide a helpful review: http://courses.chem.psu.edu/ChemTV/selmen2/ppframe.htm
Take a look at the lectures labeled "Topic 4." Much of our discussion is presented here. (Don't spend time on the stuff we didn't discuss.) By the way, you might find parts of Topics 1, 2 and 3 useful too.

Another resource: http://ochem.jsd.claremont.edu/tutorials.htm#

A. Alkenes

1. Structure -- planar geometry, p electron situated on both sides of the plane, lack of free rotation, "sidedness"

2. Nomenclature -- a) basic terms: methyl C and H, methylene C and H, methyne C and H, vinylic C and H, allylic C and H  b) common naming of alkenes c) IUPAC naming d) the functional group hierarchy e) geometric isomer cis/trans and E/Z systems

B. Reactivity

1. * Positive and Negative things are attracted to one another!, Nucleophiles and Electrophiles

2.Reaction Mechanism = tracking electrons from Nu to E with curved arrow notation.
See Solutions Manual that accompanies the text for "Special Topics II."

3. Thermodynamics and Kinetics
a) Keq>1 vs. <1; DG^o _rxn   enthalpy component, entropy component, relationship to Keq
b) reaction rates:  Rate equation; How are A, Ea, and T related to the rate constant? How are these components involved in making reactions go faster?
c) Rxn coordinates: transition states, intermediates, thermodynamics vs. kinetics in determination of major product

A. General Mechanism and Reaction Coordinates

B. Reactions

1. Addition of HX
Produces more stable carbocation intermediate - carbocation rearrangements

2.Acid catalyzed addition of H-OH and R-OH
Produces more stable carbocation intermediate - carbocation rearrangements

3. Addition of X₂
cyclic halonium ion intermediate - anti addition - Does solvent participate in reaction?

4.Oxymercuration / Alkoxymercuration
cyclic mercurinium ion

5.Addition of Peroxyacid
concerted mechanism - product = epoxide

6. Addition of Carbene
reagent = diazomethane ; product = cyclopropane derivative

7. Hydroboration followed by oxidation
"anti-Markovnikov addition"  useful for the synthesis of 1^o alcohols
Don't bother with the entire mechanism;  Understand orientation at which BH₃ adds across double bonds.
Know reagents for 1st and 2nd steps and predict product.

8. Catalytic Hydrogenation
C/ metal catalyst - syn addition

A. Stereoisomerism
1. constitutional isomers vs. cofigurational isomers, geometric isomer vs. isomers with asymmetric centers (stereoisomers);

2. enantiomers

3. R/S system of describing stereocenter

4. Fischer Projections,

5. Interconverting from Fischer to either Newman or perspective and vice versa;

6.Optical activity: rotation of plane polarized light dextrorotatory (+) vs. levorotatory (-), incorparating this property into the name,  Using the equation: specific rotation = observed rotation/ (concentration x pathlength), calculation of enantiomeric excess, racemic mixture;

7.Compounds with 2 or more chiral centers, enantiomers vs. diastereomers, erythro isomers vs. threo isomers, meso compounds (compounds with stereocenters, but no net optical activity.

B. Reaction Stereochemistry

1. Vocabulary: regioselective rxns, stereoselective reactions, stereospecific reactions, enantioselective reactions.

2. Reactions reviewed with stereoisomerism in mind:
     One new stereocenter ---> enantiomeric pair = racemic mixture
     One new stereocenter + pre-existing stereocenter --> diasteromeric pair

     Two new stereocenters:

a) Rxns involving carbocation intermediates  -- When 2 new stereocenters are made: two pairs of enantiomers

b) Rxns involving cyclic intermediates = "Anti Additions" -- When 2 new stereocenters are made: cis -->  threo
and trans --> erythro

c) Catalytic hydrogenation = "Syn Additions" -- When 2 new stereocenters are made: cis -->  erythro
and trans --> threo

A. IR Spectroscopy - Useful in identifying functional groups present

Many bonds vibrate with frequencies in IR range, various bond stretches and bond bends, IR spectrum is %T vs. wavenumber

1. Band Position: -- largely determined by Hooke's Law Lighter atoms vibrate at higher frequencies, stronger bonds vibrate at higher frequncies. See correlation chart

2. Band Intensities -- determined by polarity (the more polar, the more intense), number of a type of bond, sample amount, Note that bands tend to be characteristically sharp or broad.

See notes for "Steps in interpreting an IR spectrum."

B. UV-VIS Spectroscopy

HOMO --> LUMO , non-bonding e and p e are promoted to p* molecular orbitals,
Conjugation of double bonds decreases the E for HOMO --> LUMO, and therefore increases the wavelength at which a compound absorbs -- IN other words, the greater the conjugation, the greater the wavelength absorbed.

Conditions affecting the structure of a compound can lead to "red shift" vs. "blue shift."

Beer-Lambert Law A = elc  A useful in determining the concentration of a sample, and useful in determining the rate of a reaction. (See the example reaction of lactate dehydrogenase in which: NADH --> NAD+)

C. Mass Spectrometry

1. Instrumentation: http://www.ochem.com/  See mass spectrometry tutorial.

2. molecular ion, base peak, fragmentation patterns, relative abundance, M+1 peak, M+2 peak, "Rule of 13" , mass specs of hydrocarbons, alkyl halides: heterolytic cleavage vs. homolytic cleavage = a cleavage, ethers:
heterolytic cleavage vs. homolytic cleavage, alcohols: loss of H2O, (hetero vs. homolytic cleavage) Ketones: homolytic cleavage and McLafferty rearrangements.

A. C-13 NMR
Number of Signals -Equivalent carbons, chemical shift, C-13 DEPT NMR

B. H-1 NMR
Number of signals, Chemical shift, Intensity of signals, splitting of signals, coupling constants and splitting trees, enantiotopic groups, diastereotopic groups

A. Nomenclature

IUPAC -- give "yne" ending , ene before yne in name , give yne lower numbering if there is a choice.
Common -- substituents on acetylene, ethynyl group, propargyl group

B. Properties

Trends in boiling points for similarly sized alkanes vs. alkynes and for internal vs. terminal alkynes.

C. Reactivity and Reactions -- See Summary of Reactions on pages 282-283
1. Alkynes are a little less reactive then corresponding alkenes --they generate less stable intermediates
2. Reactions: a) Addition of HX b) Addition of X₂ c) Addition of H₂O d) hydroboration e) hydrogenations
f) Reduction by Alkali metals, g) Alkylation of terminal alkynes

D. Organic Synthesis
Design a series of reactions to generate a desired product from a smaller, simpler staring material.

A. Depicting Delocalization

B. Reactions of Dienes

A. Combustion -  straight-chain vs. branched alkanes, refineries

B. Radical Halogenation - Predicting product distribution with probability and reactivity; Experiment

C. Reactions of Cyclopropane