Syllabus

CHE 535 Synthetic Organic Chemistry Spring 2007

Please read. The following text serves as a contract between you, the student and me, the instructor.

Prerequisites.

CHE 232 at U. Kentucky or Sophomore Organic Chemistry taken elsewhere should give you enough background for CHE535.
Some command of the following is assumed. If you are unfamiliar with any, please use the index of your favorite Organic Chemistry textbook.

1. examine a Lewis structure and determine if it is likely nucleophilic or electrophilic
2. rearrangement of carbocations
   
3. arrow formalism, the language of Lewis structures
   
4. the basics of: addition of HX to alkenes or alkynes (eg. hydrohalogenation)
5.           addition of X₂ to alkenes or alkynes (halogenation)
6.           catalyzed addition of H₂ to alkenes or alkynes (hydrogenation)
7.           hydroboration/oxidation
8.           ozonolysis of alkenes
9.           the S_N2 and S_N1 reactions
   
10.           the E2 and E1 reactions
11.           dehydration of alcohols to alkenes (related to item 9)
    
12.           oxidation of alcohols to ketones and aldehydes
    
13.           the chemistry of carboxylate groups. What are easy ways to make esters?
    
14.           Diels-Alder reaction
15.           Birch (dissolving metal reduction) reduction
16.           the concept of aromaticity
17.          electrophilic aromatic substitution 
    
18.          stereochemistry (as covered in the plain vanilla sophomore organic textbook)
19.          the conformations of cyclohexane.

As you read synthetic organic chemistry you will always find an acronym with which you are not familiar. I still do. I prepared the following document to assist you: ACRONYMS.

LECTURE NOTES will be available online at the homepage.

ATTENDANCE is mandatory. We have a small class size. Your presence is necessary for critical mass and class room dynamic. The reasons for absence that are excused by U. Kentucky will of course be excused by me. For all other absences, please communicate with me. I will give easy pop quizzes that will amount to one 5 point problem assignment.

Questions during lecture

Please ask questions during lecture. Do not feel that you are interrupting me. By asking me questions you help me teach the course. I wish I could eaves drop on your mental processes. I would respond to this information. Since I am not clairvoyant, your valuable questions in class will have to suffice.

Questions outside the lecture hall

E-mail me to get on the chem-535 list. E-mail questions to a.cammers@uky.edu with subject line 535-question. I will respond to your questions by sending answers to everyone on the list. I will not reveal your identity in my answers. 

Grading Policy

CHE535 will be graded solely on the basis of two cumulative exams and three out-of-class assignments. The point value of these opportunities escalates as the semester progresses. Thus, you will have a chance to acclimate to my teaching style (hopefully) and accumulate knowledge in synthetic organic chemistry before the grade earning opportunities have a chance to really damage your class grade. Warning: the official midterm will not be the grade-point center of gravity in CHE535.

The grade earning opportunities contribute toward your final course grade in the following manner:
Midterm EXAM: 20%
Final EXAM: 40%
Problem 1: 5% (teams of three or four)
Problem 2: 15% (teams of two)
Problem 3: 20% (work alone)
          You have the option to work alone on the problems 1 and 2.
After the problem assignments have been handed back, if you did not turn in your homework, there will no opportunity to make up the points.

PROBLEM ASSIGNMENTS will be announced in class and posted at the homepage. 
I reserve the right to give announced and unannounced pop quizzes that could but will not necessarily contribute as much as 15% to your final grade.

Sample Problem

If you are ill to the point that your classes are adversely affected, please tell me right away (email or phone). In the event of illness please get a doctor's note.

If you have an academic conflict with any of the exam times, listed below in the schedule, you must see me within the first two weeks of the term. In accordance with University procedures, you must provide written notice, and this must be done for each exam with which you have conflicts. An e-mail message will serve as written notice. If an emergency rises that would produce a conflict you must notify me as soon as humanly possible.

If an exam is miss-graded, mark the number of the problem in question on the front page of the exam and return it to me within one week from the day the exam was returned. Exams returned for regrading after more than one week from the day the exam was returned will not be considered for regrading. Changing an answer prior to requesting that an exam be regraded is cheating and will result in a minimum penalty of an E in the course, in accord with University rules.

I can guarantee the following grades per total points earned:

75%-100%	A
60%-74%	B
45%-59%	C
35%-44%	D
0%-34%	E

I reserve the right to decrease the cutoffs in order to raise the overall grade point average of the class, if I deem this is appropriate. I will not raise the cutoffs and lower grades. This means that everyone in the class can potentially receive an A. The exams and problems are difficult so do not assume the above grading scheme is going to translate into an easy A for you because you have always been able to get 75% of all possible points in every class. I typically see 1 out of 20 students in the >90% category.

Makeup Exams

Please contact me as soon as possible if you will be unable to attend one of the scheduled examinations. You need to communicate with me before the exam is given to be able to take an alternate exam. Exams given to replace missed exams must be completed within one week of the original exam date. If an exam is missed without an excused absence, a '0' will be recorded as the score for that exam. The University of Kentucky's manual on Students' Rights and Responsibilities defines valid excuses for missed exams. Please note - a conflict with a work schedule is not a valid University excuse for missing an exam. If you have a job and your employer expects you to be working during one of the exam times, arrange to take time off or arrange for someone else to work your shift for you.

Tentative Class Schedule

o        January 10 Thursday - First day of class

2. (The structure of instruction)
   
• We are not going to learn [about] a bunch of organic reactions.
  
• We are going to use architectural principles, precedence, and theoretical grounds to argue for the ability to construct molecules. This focuses our study toward.
  
• Synthetic chemistry literature.
• The common components of molecular structure impede synthesis.
  
• Process design  and strategy.
  
3. (INTRODUCTION) What is Organic Synthesis?
• finding information
• convincing others you can do it, synthetic proposals
• synthons and retrons
• molecular complexity
• symmetry
• retrosynthetic analysis
• organic oxidation state
• oxidation and reduction protocols
• functionalization/ defunctionalization
• functional group manipulation
• protecting groups
• All of the above in Eaton's Synthesis of Cubane
4. (LINE LAND) Synthesis of alkynes
• by alkylations
• by Pd-catalyzed reactions
5. (FLAT LAND) Synthesis of alkenes and substituted arenes, an appreciation of the importance of stereocontrol
• challenge of stereochemical control in the synthesis of trisubstituted alkenes.
• alkenes from alkynes
• alkenes by eliminations
• alkenes by Wittig and Wittig-type reactions
• alkenes from alkenyl and aryl halides
• alkenes by olefin metathesis
• sigmatropic rearrangements (alkene and functional group transposition, allyl-mediated chemistry)
6. MIDTERM EXAM Tuesday February 27
March 5 - Monday - Official Midterm of 2007 Spring Semester: midterms grades issued to every student.


7. (COMPLEX TOPOLOGY) sigmatropic rearrangements and stereocontrolled quaternary and tertiary tip³ carbon atoms.
8. (CONTROLLING STEREOCHEMISTRY) Carbonyl chemistry // Aldol Reactions
• <topics 6 and 7 will be tackled at the same time to allow us to compare techniques>
  
March 12-17 - Monday through Saturday - Spring Vacation - Academic Holidays
• organometallic additions
• alkylations
• Michael reactions
• carbonyl condensation reactions
• asymmetric synthesis via enolates
• ring-forming reactions
9. (CONTROLLING STEREOCHEMISTRY) Synthetic Chemistry of the epoxide group
• Sharpness epoxidation
• Stereoselective ring opening
• Payne rearrangement
10. (COMPLEX TOPOLOGY) cycloadditions

April 27 - Last day of classes Go to our class homepage.