CHE 535
Synthetic Organic Chemistry

VITAL INFORMATION

Instructor: Dr. Robert B. Grossman
Office: CP-339
Telephone: 257-1285
E-mail: robert.grossman@uky.edu
Office Hours: by appointment (just email me)

Textbooks.

The textbook for this class is the library. However, you will need a good set of molecular models. You might also find yourself referring back to your sophomore organic textbook to gain some remedial knowledge. Some books you may want to purchase:

• F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry, Part B, Reactions and Synthesis
• M. Smith and J. March, Advanced Organic Chemistry
• R. C. Larock, Comprehensive Organic Transformations

Lecture notes

• First set of lecture notes.
• Second set of lecture notes.
• Third set of lecture notes.
• Fourth set of lecture notes (alkynes).
• Fifth set of lecture notes (alkenes).
• Sixth set of lecture notes (functional groups).
• Seventh set of lecture notes (carbonyls).

Exams

There will be a midterm exam, worth 30% of your grade, and a final, worth 35%. The exams will be open-book, but you will work individually.

• The 2008 midterm exam will be on Tuesday, Mar 4, 2008, at 8 am (in class).
• The 2008 final exam will be on Wednesday, Apr 30, 2008, at 10:30 am.
• Example midterm from Spring 2006.
• Example final from Spring 2006.

Assignments

The rest of your grade will be derived from your performance on four out-of-class assignments. To complete these you can work with partners in groups of two or three. You may also choose to work alone on any particular assignment. You must work with a different partner for each assignment. You may work with the same person twice only if you have worked with everyone in the class at least once.

• Problem Set 1, due Tue, Feb 12 (key).
• Problem Set 2, due Tue, Feb 26 (key).
• Problem Set 3, due Tue, Apr 1 (key).
• Problem Set 4, due Tue, Apr 15 (key).

Please note:

1. All references cited in problem sets must be accompanied by a printout or photocopy of the first page of the article and the page of the article on which the cited reaction appears, and the cited reaction and conditions must be highlighted or circled in red. I will not search papers to find the reaction you are citing as precedent.
2. Do not cite reactions from sophomore textbooks or search engines (including Beilstein). Only the primary literature should be cited.
3. Not all journals are available online. If a reference you need is not available online, hie thy butt down to the library. Interlibrary loans can get you articles from journals not carried at UK. Much of the old Russian literature is available in translation, and many people around the Chemistry department can fight their way through an article in German.

Graduate students will be differentiated from undergraduates by having to complete one additional assignment. The graduate students will be asked to compare the synthetic approaches to a single target compound (natural product or drug substance) that has been prepared three times. The target must not have been the subject of a published review article. This assignment will be due the last day of class. Undergraduates may do the assignment and use it to replace their lowest homework grade.

Guide to Using the Literature Properly.

Tentative Class Syllabus

1. What is Organic Synthesis?
   • finding information
   • synthons and retrons
   • molecular complexity
   • retrosynthetic analysis
2. Synthesis of alkynes
   • by alkylations
   • by Pd-catalyzed reactions
3. Synthesis of alkenes and substituted arenes
   • from alkynes
   • by eliminations
   • by Wittig and Wittig-type reactions
   • from alkenyl and aryl halides
4. Functional group manipulation
   • juggling functionality and heteroatoms
   • protecting groups
   • oxidation and reduction protocols
5. Carbonyl chemistry
   • organometallic additions
   • alkylations
   • Michael reactions
   • carbonyl condensation reactions
   • asymmetric synthesis via enolates
   • ring-forming reactions
6. Pericyclic reactions
   • cycloadditions
   • sigmatropic rearrangements

Prerequisites

1. identification of nucleophiles and electrophiles
2. rearrangement of carbocations
3. addition of HX to alkenes or alkynes (hydrohalogenation)
4. addition of X₂ to alkenes or alkynes (halogenation)
5. catalyzed addition of H₂ to alkenes or alkynes (hydrogenation)
6. hydroboration/oxidation
7. ozonolysis of alkenes
8. the S_N2 reaction
9. E2 reaction
10. oxidation of alcohols
11. dehydration of alcohols
12. formation of esters (what is the easiest way to make an ester)
13. Diels-Alder reaction

Additional resources on Web

• Literature search software and tools:

  • How to acquire the Beilstein software. You will also need to get access codes (group name, username, and password) from the Chemistry–Physics librarian, Jan Carver. You can use this program from home.

  • To acquire the SciFinder Scholar software (Chemical Abstracts), you need to go to the UK download site. Enter your UK username and password, choose your operating system, and list All Files. You will also need to get access codes from the Chemistry–Physics librarian, Jan Carver. You can use this program from home if you use the VPN program (also available from the UK download site) to connect to UK first.

  • Web of Science (Science Citation Index). You can use this Web site from home if you use the VPN program (also available from the UK download site) to connect to UK first.

  • A free bibliography of all organic chemistry review articles in English.

  • Links to selected online chemistry journals of interest to synthetic organic chemists.

• MarvinSketch, a free, Java-based organic structure-drawing and molecular mechanics program.

• Basic organic chemistry concepts review materials:

  • Stereochemistry help.

  • Links to sites listing acronyms, name reactions, named reagents, named rules and effects, and pK_a values.

  • Substitution and elimination handouts.
    • Instructions for drawing substitution and elimination products.
    • Instructions for determining whether substitution or elimination will occur.

  • How to go about drawing mechanisms, including free-radical chain mechanisms.

  • Check it out: IUPAC's free online compound naming service. Draw a structure and have the computer calculate its name for you!

  • William H. Reusch's Virtual Textbook of Organic Chemistry.

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This page was last updated January 17, 2006.