110A Exam 1 Review Sheet-Fall Semester 2013 Review Session: Wednesday, September 18th, 7:00 PM, SN Aud updated 9/18/13 Chapter 1: The story of tetrodotoxin; vitalism and how the concept ended; Wohler; Kolbe; Couper, Kekule, Butlerov and the structural theory; valence; tetravalence of C, bivalent forms of electrondeficient C; valence of H, O, N, S, P, F, Cl, Br, I; rules for writing resonance structures; criteria for evaluating contributing resonance structures; Lewis structures- rules for writing and assigning formal charges; application of VSEPR theory; atomic orbitals; atomic orbitals on C; construction of orbital hybrids; molecular orbitals; sigma bonds; pi bonds; rotation about single bonds; hindered rotation about double bonds; polar covalent bonds; convention for assigning dipole moments; polar vs. non polar compounds; condensed structural formulae, bond-line formulae, isomerism; constitutional isomers. Chapter 2: functional groups as outlined in the lecture; 1°, 2°, and 3° nomenclature for alcohols and alkyl halides; 1°, 2°, and 3° nomenclature for amines; cis and trans isomerism in alkenes; protic vs aprotic solvents; polar vs nonpolar solvents (solvent dielectric and dipolar nature); bonding picture of methane, ethane, ethylene, and acetylene; intermolecular forces: ionic, dipole-dipole, hydrogen bonding, attractive van der Waals; solubility of organic compounds. Infrared spectroscopy- criterion at the molecular level for allowed IR transition, mass and force-constant dependence for absorption, can you identify candidate compounds for a given IR spectrum, given a table of IR absorption frequencies? Chapter 3: Lewis acids and bases; Bronsted-Lowry acids and bases, conjugate acid and conjugate base; the dissolution/ionization of CO2 (or any weak acid) into water: can you compute the pH of the resulting solution?; relationship of pKa and pH; Henderson-Hasselbalch Eq.; typical pKa's in methane, ethylene, acetylene (reason for the trend), ammonia, hydrogen, water, alcohols, acetic acid, ammonium ion, hydrochloric acid; inductive effects, resonance effects, hybridization effects which stabilize or destabilize the anion. How acidity is affected by solvent; reasons for non-aqueous solvent conditions for much organic acid/base chemistry; arrow notation for writing reactions; acid-base reactions always favor the formation of the weaker acid and weaker base; synthesis of deuterium and tritium labeled compounds.