Electronic Configuration

Reusch
  1. Pauli Exclusion Principle:
    • Only 2 electrons per orbital (opposite spin)
    • Electrons like to be unpaired if possible
  2. Types of bonds: covalent and ionic
  3. Valence Periodic Table
  4. Solving Lewis Structures
  5. Resonance Hybrids and curved arrow formalism
  6. Lewis, skeletal and condensed structural formulas
  7. Molecular and empirical formulas
  8. 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
  2. 2 groups of electrons
    • linear
    • sp
  3. 3 groups of electrons
    • trigonal planar (120o)
    • sp2
  4. 4 groups of electrons
    • tetrahedral (109o)
    • sp3
  5. Pi and Sigma bonds-the ethylene example
  6. Rigidity of Double Bonds
  7. Isomerism- structural isomers and stereoisomers (geometrical isomers)
  8. Bond polarity and dipole moment
    • Molecule Polarity: sum of dipole moments
  9. 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)
  10. Structure and physical properties
    • Melting point (higher for stronger intermolecular forces)
    • Boiling point (higher for stronger intermolecular forces)
    • Solubility (like dissolves like)
  11. 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
  2. Nomenclature
    • isopropyl, isobutyl, n-butyl, sec-butyl, t-butyl,
  3. Primary, Secondary, Tertiary, Quaternary centers
  4. Reactions of Alkanes
    • combustion
    • cracking
    • halogenation
  5. Conformations of ethane, propane, butane
    • Newman projections
    • Steric Hindrance
  6. 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

Problems (click image for solution)

shiftmania1.jpg

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

Alkynes


Nomenclature


Acidity of alkynes


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)

Problems

orgo003.JPG