Structure of Xylomollin --- You should construct both the cis and trans fused bicyclic ring systems and minimize using PCSpartan Plus software (S303 or S243). Once minimized, check to see if the structure is reasonable. Then, find all H-H dihedral angles. Use these values in conjunction with the Karplus equation to generate a listing of expected J values (coupling constants). Compare the derived J values with the actual values listed in Problem 4.8. Does the ring likely have a cis or trans ring fusion? Answer the question by a thorough interpretation of your data/results.
(1) Reading Assignment #1 (in preparation for the class on Sept. 28)
All
of these references are on reserve in the Wilmot Library
 | Ch. 1 (pg. 1-19) from "Classics in Total Synthesis" by K.C. Nicolaou and E.J. Sorenson |
| Ch. 1 (and BRIEFLY skim the rest) from "Organic Synthesis: The Disconnection Approach" by Stuart Warren |
| Ch. 1 (pg. 1-9) from "Protective Groups in Organic Synthesis" by Theodora Greene and Peter Wuts |
| Ch. 1 (pg. 1-16) from "The Logic of Chemical Synthesis" by E.J. Corey and Xue-Min Cheng |
| Ch. 1 and 2 (pg. 1-24) from "Guidebook to Organic Synthesis" by Raymond Mackie, David Smith, and R. Alan Aitken |
(2) Reading Assignment #2 (as a follow-up to the class on September 21) ---
you should only have to skim this material
All
of these references are on reserve in the Wilmot Library
| Ch. 1, 7, and 8 from "Understanding Organic Reaction Mechanisms" by Adam Jacobs |
| Ch. 1 from "A Primer to Mechanism in Organic Chemistry" by Peter Sykes |
| Ch. 1 from "Advanced Organic Chemistry: Reactions and Mechanisms" by Bernard Miller |
(3) Problems that we will work on in class (I'll bring these as handouts for you)
| From "Advanced Organic Chemistry" by Bernard Miller --- Ch. 1 (#1 and #2) |
| From "Organic Reaction Mechanisms" by William Groutas --- # 1, 7, 14, 17, 22, 23, 27, 34, 53, 54, 57, 69, 79, 81, 93, 107, 162, 201, 204 |
(4) Homework Problems
| Skim Ch. 4-6 from "Advanced Organic Chemistry: Reactions and Mechanisms" by Bernard Miller and do (some of) the following problems: Ch. 2 #1-4, Ch. 3 #1, 3, Ch. 4 #1-3 |
| Any we did not get to in class. |