Fall 2011
Lecture MWF, 10:10-11 AM in 101 Brown Labs
Professor Joseph M. Fox
272 Brown Labs
302-831-0191
jmfox@udel.edu
Office hours: Mondays 11-12, or by appointment. Contact me by email to schedule an appointment.
Help Session
Teaching Assistant Samantha Brannick will hold a help session on Tuesdays in 101 Brown Lab from 5-6 pm
Links
Prior years of Chem 331 serve as an excellent resource for exam questions.
for questions from the last time Fox taught 331, see: http://www.udel.edu/chem/fox/chem331332.html
for questions from years Taber has taught 331, see: http://valhalla.chem.udel.edu
For a link to Chem 333, see: http://valhalla.chem.udel.edu
Textbooks:
• All students enrolled in Chem 333 (any section) should purchase: 'Organic Structure Determination', by Taber, ISBN: 9780195314700.
• Students enrolled in Chem 333-010 (Lab and Discussion section) should ALSO purchase: 'Organic Chemistry Laboratory' by Bell, Clark and Taber, ISBN: 9780030292729. Alternatively, students may purchase the Custom 331/333 Lab Manual ISBN: 9781133690986.
The following texts are also required for Chem 331:
• Required: Organic Chemistry, Vollhardt and Schore, 6th Edition, ISBN: 9781429204941
• A Molecular Model Set is required
• A 'clicker' is required
• Optional: 'Organic Chemistry Study Guide and Solutions Manual', 6th edition, Schore, ISBN: 9781429231367. Copies of this text will be available on reserve in the library.
Grading
There will be three hour exams, three quizzes and a final exam. Exams 1-3 will each be worth 20% of the final grade. Quizzes will each be worth 5% of the grade. The final exam will be worth 25% of the grade. Quizzes are CLOSED BOOK/NOTES. Exams are open book/notes Molecular models are allowed during exams.
Exam dates
Sept 30, Quiz 1 quiz 1.pdf quiz1answers.pdf
Oct 5, Exam 1 2011Exam1.pdf Exam1_KEY.pdf
Oct 26, Quiz 2 quiz 2 2011.pdf quiz 2 2011 answers.pdf
Oct 28, Exam 2 exam 2.pdf Exam 2 answers.pdf
Nov 18, Quiz 3 quiz 3.pdf quiz 3 answers.pdf
Nov 21, Exam 3 Chem 331 exam 3.pdf Chem 331 exam 3 answers.pdf
Syllabus:
Weeks 1 and 2: (Friday September 2, then Wed Sept 7, 9). Reading assignment: Vollhardt and Schore (V&S), Ch 1, 2 and 4
structure and bonding of organic compounds; Lewis dot structures, hybridization, electronegativity
Reading assignment: V&S, Ch 2;Ch 4. nomenclature handout.pdf and reading from V&S cited therein
free energy diagrams; organic functional groups; IUPAC nomenclature, conformational analysis, chair cyclohexane, Newman projections
Week 3: (Monday September 12th) Reading assignment: V&S, Ch 2;Ch 4. nomenclature handout.pdf and reading from V&S cited therein
free energy diagrams; organic functional groups; IUPAC nomenclature, conformational analysis, chair cyclohexane, Newman projections
LINKS:
• A nice overview of Hybridization theory
http://www.youtube.com/watch?v=d1E18tBTlBg&feature=youtube_gdata_player
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•chair cyclohexane--online visualization aids
http://www.youtube.com/watch?v=bPLREpfZ63I
http://www.youtube.com/watch?v=1e3ydZLsL1A&feature=related
http://www.youtube.com/watch?v=rI0qVMUBQHc&feature=related
• IUPAC practice--To practice IUPAC, you can use Reaxys
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1)Open Reaxys
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2)Double click in the frame
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3)Draw a structure
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4)Under “tools”, select “naming”. Then hit OK
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5) The IUPAC name for the structure you drew will appear
Week 4: (Monday September 19). Reading: Ch 5
Fischer projections, Newman projections, R vs. S, diastereomers, enantiomers, more IUPAC names
HANDOUT: Chirality handout revised.pdf
Week 5: (Monday September 26). Quiz on Friday! homolytic vs. heterolytic; free-radical halogenation, bond-forming, bond-cleaving reactions. Reading: Chapters 3 in V&S. Take note of Tables 3-1 and 3-2 on pages 97-98. Also, Read pgs 612-614, Radical Allylic Halogenation.
Be sure to read these handouts: radicalhandout.pdf
in addition to reading see additional handout on Taber's website: Bu3SnH
Week 6: (Monday October 3rd) Exam 1 on Wednesday OCT 5!
Reading Ch 6. In addition read pg 350-355, Williamson Ether synthesis
Also read ester hydrolysis, pg 938
Week 7: (Monday October 10)
SN2 reactions.
Links: Sn2 visualization tools
http://www.youtube.com/watch?v=pTp0R6WuSks&feature=related
also see
http://chemistry.berkeley.edu/links/mpg_files/sn2.mpg
I thought this one was funny
http://jchemed.chem.wisc.edu/JCESoft/CCA/CCA5/MAIN/1ORGANIC/ORG10/TRAM10/F/0323822/PICTURE.HTM?1
Week 8: (Monday October 17th). Read chapter 7
Acid-mediated mechanisms. also read pg 335-344
SN1 visualization tool:
http://www.youtube.com/watch?NR=1&v=yJlSTWED8Iw
Week 9: (Monday October 24) Quiz on Wednesday, Exam on Friday!
begin E1, E2 elimination; conformational analysis, acid-mediated mechanisms
Week 10: (Monday October 31) Reading: Chapters 8 and 9 in V&S and pp 532-534 (epoxidation) in V&S.
hydride reductions, SN2 reactions, nucleophilicity, acidity
Week 11: (Monday November 7) Reading: pages 884-885 (nitrile hydrolysis) and 956-957 (nitrile to ketone using organometallics).
functional group interconversions, arrow-pushing mechanisms, stepwise synthesis, Grignard reactions
Week 12: (Monday November 14) Quiz on Friday!
alkene additions, stepwise reactions, stereochemical reasoning
Week 13: (Monday Nov 21) Exam on Monday! No class on Wed or Friday (Happy Thanksgiving)
Week 14: (Monday Nov 28)
alkene construction, Wittig reaction (pg 804-807),
alkyne chemistry; special handout: alkyne zipper: http://valhalla.chem.udel.edu/zipper.html
Week 15: (Monday Dec 5) Review for final - last class Wednesday December 7th