Registration woes: E257, 822-5710; or Dr. Bates (D303, 822-2834)
Lab: Dr. Cliff (C326b, 822-6878, )
Grade breakdown: Lab: 30%, midterm, 25%, final, 45%. Midterm: Monday, October 27.
In any Science course which has both laboratory work and written examinations, students must complete and pass both parts to pass the course. Failure to meet the above requirement of the Faculty of Science will result in the student's grade being lowered to that of a failing grade (45%) despite the actual numerical sum of the laboratory and lecture components of the course.
Text: No formal text, use what you have as a reference and for review. Advanced Organic Chemistry Part B (Carey & Sundberg) is on reserve at the Library and can be purchased at the bookstore.
Problem Sets: Will be posted on the web (not graded), as will be answers. Last year’s midterm and answers and last year’s final and answers will be posted on the web. Handouts are posted on the web, as are some relevant papers from the chemical literature. (Web:www.chem.ubc.ca; select "courseware," then "330")
COURSE OUTLINE
1. Synthetic Methodology : C—C Bond Formation
(a) Review of acid/base chemistry
(b) Regiospecific formation of ketone enolates; thermodynamic and kinetic enolates
(c) Alkylation & Intramol. alkyln. of ketones
(d) Alkylation of esters, lactones, nitriles, aldehydes
(e) Conformational analysis and enolate attacks with decalones, etc.
(f) Claisen ester condensations ; Dieckmann
(g) Enone synthesis & reactions
(h) Conjugate addition (Michael reactions)
(i) Aldol & intramolecular aldol
(j) Diastereo- and enantio-selective aldols
(k) Robinson annulation
(l) Intermolecular and intramolecular Diels-Alder reactions
(j) Diastereo- and enantio-selective Diels-Alder reactions
2. Carbocation Rearrangement reactions
(a) Carbocation stability
(b) Hydride, alkyl shifts
(c) Neighboring group participation
(d) Phenonium ion
(e) Classical versus non-classical carbocations