Fall 2011

Lecture MWF, 10:10-11 AM in 101 Brown Labs

Professor Joseph M. Fox

272 Brown Labs



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


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


• 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.


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


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


• A nice overview of Hybridization theory


  1. chair cyclohexane--online visualization aids



IUPAC practice--To practice IUPAC, you can use Reaxys   

  1. 1)Open Reaxys

  2. 2)Double click in the frame

  3. 3)Draw a structure

  4. 4)Under “tools”, select “naming”.  Then hit OK

  5. 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


also see

I thought this one was funny

Week 8: (Monday October 17th).  Read chapter 7

Acid-mediated mechanisms.  also read pg 335-344

SN1 visualization tool:


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








Chem 331 Fall 2011