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.