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=Electronic Configuration= [|Reusch]
 * 1) Pauli Exclusion Principle:
 * Only 2 electrons per orbital (opposite spin)
 * Electrons like to be unpaired if possible
 * 1) Types of bonds: covalent and ionic
 * 2) Valence Periodic Table
 * 3) Solving Lewis Structures
 * 4) Resonance Hybrids and curved arrow formalism
 * 5) Lewis, skeletal and condensed structural formulas
 * 6) Molecular and empirical formulas
 * 7) Acids and Bases
 * Lowry-Bronsted Acid: PROTONS (H+)
 * Lewis Base: Lone pair of electrons

=Molecular Orbitals and Functional Groups=
 * 1) Atomic and Molecular Orbitals: the geometry of electron probability distribution
 * s, p orbitals
 * hybrid orbitals sp, sp2, sp3
 * 1) 2 groups of electrons
 * linear
 * sp
 * 1) 3 groups of electrons
 * trigonal planar (120o)
 * sp2
 * 1) 4 groups of electrons
 * tetrahedral (109o)
 * sp3
 * 1) Pi and Sigma bonds-the ethylene example
 * 2) Rigidity of Double Bonds
 * 3) Isomerism- structural isomers and stereoisomers (geometrical isomers)
 * 4) Bond polarity and dipole moment
 * Molecule Polarity: sum of dipole moments
 * 1) Intermolecular Forces ([|Reusch])
 * Dipole-Dipole interaction (e.g. CH3COCH3 acetone)
 * Hydrogen bonding (e.g. HF, H2O) NEED F,O or N and H
 * van der Waals forces (e.g. He, CH4)
 * 1) Structure and physical properties
 * Melting point (higher for stronger intermolecular forces)
 * Boiling point (higher for stronger intermolecular forces)
 * Solubility (like dissolves like)
 * 1) Functional groups
 * Alkanes, Alkenes, Alkynes, Alcohols, Ethers, Aldehydes and Ketones, Carboxylic Acids, Acid Chlorides, Esters, Amides, Amines

=Hydrocarbons=
 * 1) Let’s count to 10
 * methane, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane
 * 1) Nomenclature
 * isopropyl, isobutyl, n-butyl, sec-butyl, t-butyl,
 * 1) Primary, Secondary, Tertiary, Quaternary centers
 * 2) Reactions of Alkanes
 * combustion
 * cracking
 * halogenation
 * 1) Conformations of ethane, propane, butane
 * Newman projections
 * Steric Hindrance
 * 1) Cycloalkanes
 * Cis-trans isomerism of cycloalkanes
 * Chair and boat configurations of cyclohexane
 * Axial and Equatorial positions

=Halogenation of alkanes= [|Reusch (#2)]
 * 1) Bromination of methane ([|Reusch])
 * 2) Bond Dissociation Energy
 * 3) Homolysis and Heterolysis
 * 4) Transistion State (Predicting the geometry using the Hammond Postulate)
 * 5) Rate-limiting step
 * 6) Bromination of propane
 * 7) Chlorination of propane (loss of selectivity)
 * 8) Free-radical stabilities
 * 9) Carbocations/Carbanions

=TEST 1=

=Chirality=

R and S configurations Optical activity: detrorotatory and levorotatory Specific rotation Racemic mixture Fisher Projection Diastereomers and Enantiomers Reactions involving chiral centers

Alkyl halides
Nomenclature

Preparation
1) Free-radical halogenation 2) Hydrohalogenation of alkenes 3) From alcohols 4) From other alkyl halides

Reactions 1) elimination 2) nuleophilic substitution

SN1 and SN2 reactions Solvent effects on nucleophilicity Walden inversion Rearrangements in SN1 reactions (hydride and methyl shifts of carbocations) E-1 and E-2 Reactions Satyzeff Rule

Alkenes
Unsaturation Nomenclature Z and E, cis and trans 8 Carbon Rule Preparation 1) Dehydrohalogenation 2) Dehalogenation 3) Dehydration of alcohols 4) Catalytic cracking of alkanes 5) Wittig synthesis

Reactions
1) elimination

2) nuleophilic substitutionSN1 and SN2 reactions

Solvent effects on nucleophilicity

Walden inversion

Rearrangements in SN1 reactions (hydride and methyl shifts of carbocations)

E-1 and E-2 Reactions

Saytzeff's Rule

Alkenes
Unsaturation

Nomenclature
Z and E, cis and trans

8 Carbon Rule

Preparation
1) Dehydrohalogenation

2) Dehalogenation

3) Dehydration of alcohols

4) Catalytic cracking of alkanes

5) Wittig synthesis

Reactions:
Electrophilic addition Markovnikov’s rule Anti-Markovnikov addition Hydration of Alkenes Anti-Markovnikov hydration by hydroboration Catalytic hydrogenation Simmons-Smith reaction Halogenation Hydrohalogenation Epoxidation Permanganate hydroxylation (cold, dilute) Permanganate (warm, concentrated) Ozonolysis OsO4 Carbenes

Preparation
From dihalides From acetylides (via SN2 for primary alkyl halides - secondary and tertiary alkyl halides give E-2 with alkyne salts)

Reactions
Hydrogenation Partial hydrogenation (Lindlar’s catalyst) Halogenation Markovnikov addition of HBr Hydration to ketones Permanganate (cold, dilute) Permanganate (warm, concentrated)