Download Exam 1 Review

110A Exam 1 Review Sheet- Fall Semester 2009
Review Session: Wednesday, September 16th, 7:00 PM, SN Aud
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; the amide
bond- hybridization and properties; 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; solubility of organic
acids and bases; 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.