CHEM 203 LEC A: ORGANIC SPECTRSCOPY (41400)

Organic Spectroscopy

Chem 203, Fall 2023, Course Code 41400

Lecture: 9-9:50 am, MWF, ALP 2500
Discussion: 5-5:50 pm, M, RH 108

James S. Nowick, 4126 NS 1
949-824-6091, jsnowick@uci.edu

 

Web Site
https://canvas.eee.uci.edu/courses/57646

A PDF of the syllabus is available through the course website (Syllabus.pdf).

 

Textbooks (Required)
• Spectrometric identification of organic compounds. 8th ed.
Robert M. Silverstein, Francis X. Webster, David Kiemle, and David L. Bryce. Wiley, 2014.
NOTE: The 7th edition is also OK.
• Structure determination of organic compounds: tables of spectral data. 4th ed.
E. Pretsch, P. Buhlmann, and M. Badertscher. Springer, 2009.
NOTE: The 3rd edition is also OK.

 

Additional Items (Required)
• A three-button mouse, such as the Amazon Basics 3-Button Wired USB Computer Mouse or the Logitech M510 Wireless Computer Mouse. This item is required for use in the first discussion section and in subsequent activities and exercises.

Additional Items (Recommended)
• iPad, similar tablet, or touch-screen laptop

• A good ruler, such as the C-Thru model W-30 or model 36 (clear plastic rulers graduated in cm and inches)
  • A grid that can be printed laserprinted directly on transparency film is available through the course website (Grid10V2.pdf). This item will be distributed later in the course.

 

 

Course Outline
Infrared Spectroscopy
Mass Spectrometry
Basic ¹H NMR Spectroscopy (1-D FT NMR), ¹³C NMR Spectroscopy
Advanced NMR Spectroscopy (advanced 1-D and 2-D techniques)

 

Problem Sets
There will be weekly problem sets due on Mondays immediately after discussion section, by 7 pm, and should be submitted electronically via the Canvas website.

 

Discussion Section
5-5:50 pm, Mondays, RH 108. Please be prepared to discuss homework problems.

 

Cancelled Classes and Discussion Sections
Class and Discussion Sections will not meet on the scheduled holidays of Friday, November 10 and 24.

 

Exams
Midterm: 9 am Saturday, November 11. Part I closed book, 1 hour; Part II open book, open notes, laptop computers permitted, open ended.

Final: Friday December 15 (starting at 9 am) through Sunday December 17. Open book, open notes, laptop computers permitted, open ended. PLEASE NOTE THESE DATES WHEN MAKING TRAVEL PLANS.

 

Grading
Midterm, ~40%; Final, ~45%; Problem sets and discussion participation, ~15%.

 

Teaching Assistant
Jason Zhu (jasonz13@uci.edu).

 

Office Hours and Study Sesssion
Fridays at 4-5 pm in the interaction space outside my office, 4126 NS 1.

Jason Zhu (jasonz13@uci.edu) will be available by appointment.

 

Sunday Evening Jam Session
There will be a Sunday afternoon jam session at 5-7 pm every Sunday to go over the homework before it is due that will be hosted by Jason Zhu in the interaction space outside my office, 4126 NS 1. Attendance is optional.

 

Reading Assignments
Weekly reading assignments will be posted on the Canvas course space as part of each homework assignment and are to be done prior to the due date for that homework assignment.

 

Homework Assignments and Participation
Homework will be graded and will, in conjunction with participation in the discussion sections, count for 15% of the course grade. Weekly homework assignments will be posted on the Canvas course space and are to be turned in electronically or as a hard copy shortly after each discussion section. Completion of the homework assignments is essential to success in this course.

 

NOTE: You are permitted to annotate your homework assignments during discussion using a different sort of pen or pencil. You will receive some credit for annotated answers if you show appropriate thinking and work. This does not mean that you are allowed to do your homework during discussion section, but rather that you are permitted to correct errors and provided insights on problems on which you have already made good-faith efforts.

 

Attendance
Attendance of the lecture and discussion sections is mandatory.

 

Academic Honesty
Academic honesty is strictly enforced on exams, homework, and other aspects of this course. Academic dishonesty will result in a failing grade and a letter in the student's file. NOTE THAT USE OF SOLVED HOMEWORK SETS AND ANSWER KEYS FROM PREVIOUS YEARS' CLASSES IS NOT PERMITTED AND CONSTITUTES ACADEMIC DISHONESTY.

 

While it is OK to discuss homework problems with your classmates, it is NOT OK to simply copy the answers of your classmates. Exams must be worked individually, without help or discussion from others.

 

 

 

A Selected List of Topics to be Covered

General
Degrees of unsaturation
Molecular modeling and conformational analysis
Solving structures from spectra

 

Infrared Spectroscopy
Theory, instrumentation, sample preparation
Characteristic peak positions/intensities/shapes for various functional groups
(including alkanes, alkenes, arenes, alkynes, alcohols, aldehydes, ketones, esters, acids, amides, amines, ammonium salts, nitro compounds, nitriles)
Effect of ring size and unsaturation on carbonyl peak position

 

Mass Spectrometry
Theory, instrumentation, ionization/vaporization techniques
High resolution mass spectrometry
Isotopic abundances, M+1, M+2 peaks
Fragmentation pathways
Additional topics TBA

 

¹H NMR Spectroscopy
Theory, instrumentation, sample preparation, peakshape, shimming, digital resolution, etc.
Chemical shifts (common functional groups, estimation and calculation of chemical shifts)
Spin-spin coupling (first order spectra, non-first order spectra, virtual coupling, long-range coupling, typical coupling constants)
Chemical and magnetic equivalence (diastereotopicity, enantiotopicity)
Pople Notation
Analysis of spectra as applied to determination of coupling constants and stereochemistry
Characterization of compounds by ¹H NMR
Additional topics TBA

 

¹³C NMR Spectroscopy
Theory, types of simple experiments (¹H decoupling, off-resonance ¹H decoupling, DEPT, APT)
Chemical shifts and substituent effects (common functional groups, estimation and calculation of chemical shifts)
Spin-spin coupling (¹J_CH, ²J_CH, ³J_CH, ¹³C-¹³C coupling, ¹³C-¹⁹F coupling, ¹³C-³¹P coupling, typical coupling constants, roles of hybridization, electronegativity, etc.)
Additional topics TBA

 

"Advanced" 1-D NMR
Time-dependent effects (coalescence temperature, "τ", ΔG^‡, Eyring equation)
Nuclear Overhauser effect (difference NOE, multi-spin systems, distance-effects, application to stereochemical problems)
Complex pulse sequences (the rotating frame, effects of various types of pulses, the spin-echo experiments, APT, DEPT)
¹H decoupling experiments
Additional topics TBA

 

 

 

2-D NMR
COSY (interpretation, digital resolution, contour levels)
HETCOR (H,C-COSY) and HMQC
Long-range H,C-COSY (HETCOR) and HMBC
TOCSY
INADEQUATE
NOESY
ROESY
Systematic application of 1-D and 2-D NMR data to the determination of molecular structure
HMQC-TOCSY
Additional topics TBA