This page links electronic handouts for CEM 311, Spring 2012.

• Course syllabus (PDF)
• Errata page for Miller, 2d. Ed.
  • 5 points for each new erratum.
• You need to be intimately familiar with these general trends in acidity.
  • One reason you need to be familiar with acidity trends is that basicity is inversely correlated with leaving group ability.
  • Gas Phase Studies of the Competition between Substitution and Elimination Reactions, S. Gronert, Acc. Chem. Res. 2003, 36, 848-857
    This elegant series of experiments untangles intrinsic nucleophilicity and basicity from medium effects by running reactions in the gas phase. It considers both the nucleophile's strength as a Brønsted base and the structure of the substrate.
• Lewis acids in organic chemistry
• Values of Hammet constants σ, σ⁺ and σ^- for various groups, taken from J.E. Leffler and E. Grunwald, Rates and Equilibria of Organic Reactions, Wiley 1963 (Dover reprint)
• Article considering various levels of bonding theory to explain Why doesn't carbon form a molecule with four covalent bonds?
• Article on antibonding orbitals
• Article on hybridization and electronegativity
• Article comparing the valence-bond and molecular-orbital theories' descriptions of CO and SO₄
• Article explaining Why is carbon the only element to link in long chains?
• Article explaining why we call a molecule with two unpaired electrons a "triplet" in terms of the Pauli Exclusion Principle.
• Lecture slides on valence-bond vs. molecular orbital bonding theories (PDF).
• π molecular orbitals of conjugated poly-enes (useful for thinking about pericyclic reactions)
• Pericyclic reactions with molecular models
  • Conrotatory ring-opening of cyclobutenes
  • Disrotatory ring-closing of conjugated trienes
  • Diels-Alder reactions

  Problem sets by due date

  February

  March

  April

  • 1/12/2012: Chapter 1, problems 1.1: a, b, d, e, f, g, k, l, m, n, o; 1.2b. Answer key for Chapter 1 problems is posted to Moodle.
  • 1/24/2012: Chapter 2, problems 2.3a,b; 2.4a,b,c,d.
  • 1/26/2012:Chapter 2, problems 2.4 (e, f) and 2.5 (a, b, c). Some hints:
    • 2.4e: This is similar to page 40.
    • 2.4f: This is identical to 2.4a.
    • 2.5a: The deuterium atom DOES NOT MOVE.
    • 2.5b: Be clear on what is happening in this reaction!
    • 2.5c: Nothing moves. Just a ring-open, ring close reaction. It will look very weird to you.
  • 1/31/2012: Begin reading Chapter 3. Do problem 3.1.
  • 2/2/2012: Take notes on anything you need help with in Chapter 3. Do problem 3.2, a,b,c,d,e. Pay particular attention to the geometry of approach during the cycloaddition; this will tell you what geometry the product ought to have.
  • 2/7/2012: We will finish Chapter 3 this week. Have problem 3.2, f,g,h,i,j, ready to hand in. Begin problem 3.3.
  • 2/9/2012: We will finish Chapter 3 this week. Have all of problem 3.3 ready to hand in today.
  • 2/14/2012: We will begin Chapter 4. Have problems 4.1 and 4.2 ready to hand in today.

  Exam answers

  • Midterm Exam with answers
  • Final Exam with answers