Chem 332

Spring 2010
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.

Textbooks:
Organic Chemistry, Vollhardt and Schore, 5th Edition
Organic Chemistry Study Guide, Schore
A Molecular Model Set is also required
 
Links and resources:

Chem 334  Laboratory course that accompanies Chem 332
Chem  332 from Spring 2003: resource for old problems
Chem 332 from Spring 2005
Chem 332 from Spring 2006
Chem 332 from Spring 2007
Chem 332 from Spring 2008
Chem 332 from Spring 2009
Prof. Taber's course page: resource for old problems

Handouts
polymer lecture
Handout on IR
Handout on Mass Spec
Handout on Solid Phase Synthesis and Sugar Chemistry

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.  Quizes will each be worth 5% of the grade.  The final exam will be worth 25% of the grade.    Exams are CLOSED BOOK/NOTES.  Molecular models are allowed during exams.

Exam and Quiz Schedule:
Quiz 1 on March 8
Exam 1 on March 10
Quiz 2 on April 9
Exam 2 on April 12
Quiz 3 on May 7
Exam 3 on May 10
FINAL exam TBA

FOR THOSE ALSO ENROLLED IN CHEM 334:
Chem 334 Lab Exam April 26, 7-10 pm in 101 BrL (please contact me if you have a conflict with this time/date)


in addition to end-of-chapter problems (to be assigned in class)
Problem Sets:  1   2   3   4   5   6   7   8   9   
Problem Set Answers:  1   2   3   4   5   6   7   8   9   

for more problems: Chem  332 from Spring 2003

extra synthesis problems:  1 
extra synthesis problem answers: 1  

2010 Exams:  1  2  3  4
2010 Exam Answers  1  2  3  4
2010 Quizzes:  1  2  3  4
2010 Quiz Answers  1  2  3  4

2009 Exams:  1  2  3  4
2009 Exam Answers  1  2  3  4
2009 Quizzes:  1  2  3  4
2009 Quiz Answers  1  2  3  4

2008 Exams:  1  2  3  4
2008 Exam Answers  1  2  3  4

2007 Exams:  1  2  3  4
2007 Exam Answers  1  2  3  4

2006 Exams:  1  2  3  4
2006 Exam Answers: 1  2  3  4  

2005 Exams:  1   2   3   4   
2005 Exam Answers:  1   2   3   4   


Learning Goals

The Learning Goals for this course include developing the following:
1)  a qualitative understanding of molecular orbital theory, and application to the understanding of molecular reactivity.  Students will also develop an understanding of the relationships between resonance structures and molecular orbital theory.
2) an understanding of how to apply organic reactivity to the synthesis of complex structures.
3) an understanding multistep, arrow pushing mechanisms
4) an understanding of how structure and bonding effects the properties of amines .  An understanding of methods for synthesizing amines, and an understanding of amine reactivity
5) an understanding of carbonyl reactivity using MO theory and resonance structures.  Students will also develop an understanding of methods for generating enolates, and understanding how they can engage in useful synthetic reactions
6) an understanding of the reactivity of carbonyl compounds as electrophiles, including a discussion of conjugate addition reactions.
7) an understanding of how dicarbonyl compounds are used in synthetic organic chemistry
8) an understanding of pericyclic reactions, and the molecular orbital basis for pericyclic reactivity.  Classes of reactions to be discussed include:
• electrocyclic cyclizations
• sigmatropic reactions
• cycloaddition reactions: 4+2 (Diels-Alder) vs 2+2 (photochemical) cycloadditions.  Students will develop an understanding of the basis of regio- and diastereoselectivity in Diels-Alder reactions by understanding the concept of asynchronous, concerted transition states
• carbene reactivity
9) an understanding of the synthetic utility of the reactions listed in #8.
10) an understanding of the molecular orbital basis for aromaticity, and the extension of aromaticity beyond benzenoid systems
11) an understanding of electrophilic aromatic substitution reactions, and their usefulness in synthesis
12) an understanding of nucleophilic aromatic substitution reactions, the reactivity of diazonium salts, and benzyne
13) an understanding of how organic reactivity relates to organic polymers.
14) an understanding of the structure of peptides and proteins.  Students will gain an understanding of methods for the synthesis of polypeptides
15) an understanding of the structure and reactivity of sugars and polysaccharides
   


Syllabus:
 
Week 1:    Instructions for independent study (of chem 334).   Chp.21 - Amines.  
Week 2:   Chp. 17, 18 - Aldehydes and Ketones
 
Week 3:   Ring-forming Reactions: Chp. 19, 20, 23 Carboxylic Acids, Dicarbonyl Compounds.
 
Week 4:    Ring-forming Reactions continued: Intramolecular aldol condensation, Robinson annulation, Dieckmann Review for exam 1. 
 
Week 5:  Exam 1 and Quiz 1 this week!  Sigmatropic (electrocyclic) Rearrangements, 
 
Week 6:    Diels-Alder  Photochemical 2+2 additions to make 4 membered rings.  Carbenes to make 3 membered rings. Chp. 15, 16 Chp. 22 Aromaticity; Benzene Substitution.  
 
Week 7:   Chp. 15, 16 Electrophilic Aromatic Substitution, Diazonium Salts  Aromaticity continued. 
 
SPRING BREAK

Week 8:   Chemistry of Benzene derivatives, Nucleophilic Aromatic Substitution Quiz 2 this week!
 
Week 9: Synthesis applications   Exam 2 this week!
   

Week 10:  organic polymers


Week 11:   Chp. 12, Chp. 26 Amino Acids, Peptides Lab exam 2 on Monday
 
Week 12:   Chp. 24 Sugars, Chp. 25 Heterocycles,  Quiz 3 this week

Week 13:   Chp. 26 DNA, arrow-pushing mechanisms, synthesis, Exam 3 this week!
 
Week 14:      Review for final


Bring your questions to the last class 
 
FINAL EXAM: TBA