Courses:

Methods for the determination of organic molecules, advanced principles of organic stereo chemistry, organic reaction mechanisms, and methods for the synthesis of organic compounds. Special topics illustrating the role of organic chemistry in biology, medicine, and industry.

Lectures:
Three sessions / week
1 hour / session

Recitations:
Two sessions / week
1 hour / session

Prof. Timothy M. Swager

Wade, L. G., Jr. Organic Chemistry. 4th ed.

Simek, J. W. Solutions Manual.

Several units in 5.13 will emphasize many stereochemical aspects of organic reactions and molecules. To help you visualize stereochemical concepts, we recommend that you purchase the Darling "Molecular Visions" Molecular Model Kit. You are permitted to bring model sets to all exams.

Problem sets are mandatory and will be corrected by the TAs. Problem sets will be assigned and should be handed in to your recitation instructor on the dates announced. Problem sets are posted in the assignments section of this site.

There will be four 1 hr exams in addition to the final. Exams 1, 3, and 4 will be held during the class lecture time:

Exam 1 - Lecture 8
Exam 2 - Lecture 19
Exam 3 - Lecture 29
Exam 4 - Lecture 36

Question and Answer sessions will be scheduled prior to each exam. If you have an irresolvable conflict with a scheduled exam, you must notify the Chemistry Education Office in writing of the existence and nature of the conflict and sign up for the conflict exam no later than 1 (one) week before the exam date. Conflict exams generally will be scheduled for the same day as the regular exam. If you are unable to take an exam for medical reasons, we will generally excuse you from that exam after you provide a note from the Medical Department or Counseling Services. If you require extra time for written exams because of a disability, please secure a note from the Disabilities Services Office and bring it to the Chemistry Education Office as soon as possible.

The course score will be calculated based on the values given below. You WILL NOT be graded on a curve and your grade will reflect your mastery of Organic Chemistry rather than your performance relative to your peers.

100 pts - Problem Sets
400 pts - 4 Hour Exams
200 pts - Final

Spectroscopy, Spectrometry, and Proof of Structure

(Wade, Chapters 12 and 13 and class handouts) Determination of the structure of organic molecules; emphasis on the application of infrared and nuclear magnetic resonance spectroscopy.

Molecular Orbital Theory and Pericyclic Reactions

(Wade, Chapters 15 and 16 and class handouts) Modern concepts of bonding and aromaticity. The Woodward-Hoffmann Rules. Mechanism of pericyclic reactions and applications in synthesis.

Chemistry of Functional Groups and Reactive Intermediates

(Wade, Chapters 11, 15, 19 - 22, and class handouts) Alcohols, Ethers, Epoxides, Amines, and Carboxylic Acids. Enols, Enolates.

Carbocations, Radicals, and Photochemistry

(Wade and class handouts)

What is the relationship of 5.13 to 5.12?

Much in the way that a second semester foreign language subject is related to the first semester. In 5.13 we will make constant use of the "vocabulary" (e.g. functional groups) and "grammar rules" (reaction mechanisms) introduced in 5.12, and thus one must be "fluent" in 5.12 in order to follow the new material discussed in 5.13. (We will review key 5.12 concepts as appropriate.)

What is the role of the textbook in 5.13?

We will assign reading in Wade for each unit in the course and also will suggest specific problems in both the text and study guide. We believe that you will find that the recommended "drill problems" will prove essential in mastering the material we'll be studying.

Why aren't notes handed out for each lecture, as was the case in 5.12?

Part of your educational mission at MIT is learning how to take notes on your own. We will distribute handouts in lectures that include tables, spectra, complicated structures, and other such material that is important for you to know, but is not communicated most effectively using a chalkboard or overhead projector. With this approach, you will be able to focus on what we are discussing, rather than having to worry about accurately copying items of this complexity.