Synthetic Organic Chemistry
Instructor: Dr. Robert B. Grossman
Office Hours: by appointment (just email me)
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
Will be posted here after the series of lectures is finished.
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 2015 midterm exam will be delayed until Tuesday, Mar 31, 2015, at 8:00 am (in class) due to days missed.
- The 2015 final exam will be on Tuesday, May 5, 2015, at 8:00 am.
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 a second time only if you have worked with everyone in the class at least once.
You may submit your completed assignments to me by email if you observe the following restrictions:
- You must use a word processing program to write your text and a structure-drawing program to draw structures. I will not accept assignments that consist of cell phone photographs of hand-written text or structures.
- You must submit a single file in PDF format. Do not submit Microsoft Word or OpenOffice documents, and do not submit multiple files.
- 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.
- Do not cite reactions from sophomore textbooks or search engines (including Reaxys). Only the primary literature should be cited.
- 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.
Tentative Class Syllabus
- What is Organic Synthesis?
- finding information
- synthons and retrons
- molecular complexity
- retrosynthetic analysis
- Synthesis of alkynes
- by alkylations
- by Pd-catalyzed reactions
- by metathesis
- Synthesis of alkenes and substituted arenes
- from alkynes
- by eliminations
- by Wittig and Wittig-type reactions
- from alkenyl and aryl halides
- by metathesis
- Functional group manipulation
- juggling functionality and heteroatoms
- protecting groups
- oxidation and reduction protocols
- Carbonyl chemistry
- organometallic additions
- Michael reactions
- carbonyl condensation reactions
- asymmetric synthesis via enolates
- ring-forming reactions
CHE 232 is the prerequisite for this course. I will assume you have command of the following subjects.
- identification of nucleophiles and electrophiles
- rearrangement of carbocations
- addition of HX to alkenes or alkynes (hydrohalogenation)
- addition of X2 to alkenes or alkynes (halogenation)
- catalyzed addition of H2 to alkenes or alkynes (hydrogenation)
- ozonolysis of alkenes
- the SN2 reaction
- E2 reaction
- oxidation of alcohols
- dehydration of alcohols
- formation of esters (what is the easiest way to make an ester)
- Diels-Alder reaction
Additional resources on Web
- Literature search software and tools:
- MarvinSketch, a free organic structure-drawing and molecular mechanics Java program.
- Basic organic chemistry concepts review materials:
to the UK Chemistry Home Page
This page was last updated January 5, 2015.