every effort has been made to make sure this electronic syllabus is error-free,
it is not official.
The definitive source of course information remains the original (paper) syllabus distributed in class.
Course Description - This course examines the various spectral and chemical techniques used by organic chemists to identify and characterize organic molecules. The laboratory component of the course will utilize the spectral techniques discussed in class.
Faculty - Dr. Chriss McDonald, HBC 233, 433-4493 (home, call up to 10 pm), 321-4186 (work), email firstname.lastname@example.org, no specific office hours but I'm usually around.
Texts and Other Stuff
a. Spectrometric Identification of Organic Compounds, 6th Edition, by Silverstein and Webster
b. Old 220-221 lab manual
c. Bound laboratory notebook by Freeman
d. Lab safety glasses
e. Calculator (add, subtract, multiply, divide, logs)
a. Lectures - MWF, 2:00 PM.
b. Assigned homework - problems designed to enhance your understanding and prepare you for testing situations. A key will be passed out immediately after collection of the assignment. No late homework will be accepted.
c. Laboratory - 7:45 - 11:35 R. The experiments are listed on the last page.
a. The final grade is based on the number of points obtained out of a possible 650 points. The points will be distributed as follows:
quizzes 30 points
hour exams 300 points
final exam (cumulative) 150 points
laboratory 120 points
homework 50 points
total 650 points
b. Assignment of letter grades is based on the following scale: 650-585 A, 584-520 B, 519-455 C, 454-390 D, < 390 F. A higher score on the cumulative final (adjusted to a 100 point scale) can be used to replace the lowest exam score.
c. BONUS POINTS! you will receive 3 bonus points for each chemistry department colloquium you attend (max of 12 points). There will also be some bonus questions on the exams.
Policy on Attendance for Exams and Quizzes Makeups will be administered only if I deem the reason for absence to be legitimate and I am notified of the absence beforehand. Absence due to transportation difficulties is not considered legitimate.
date topic reading quiz/test
8/25 introduction 1,
8/27 EIMS instrumentation and initial considerations 2.1,2.2,2.3
9/29 elemental analysis and hydrocarbon fragmentation 2.4,5,6,7
9/1 EIMS of various functionality 2.8-2.10
9/3 as above 2.8-2.10
9/5 CI and other ionization methods 2.5
9/8 IR theory 3.1-3
9/10 IR of hydrocarbons 3.4-6 Quiz 1
9/12 IR of other functional groups 3.6
9/15 as above 3.6
9/17 as above (in lab Thursday) 3.6
9/19 practice problems -
9/22 Raman spectroscopy -
9/24 - - EXAM 1(in lab)
9/26 NMR review 220/221 lab manual
9/29 NMR theory 4.1-6
10/1 proton chemical shift 4.7
10/3 protons on heteroatoms (in lab on Thursday) 4.9
10/6 coupling phenomena 4.8
10/8 chemical shift equivalence and molecular topology 4.7,4.10,4.4
10/10 multiple couplings 4.8,4.12
10/13 more coupling issues 4.13-16, 4.22 Quiz 2
10/15 problems -
10/17 Karplus relationship and long range coupling 4.17
10/20 spin-spin decoupling 4.19
10/22 - - EXAM 2 (in lab)
10/24 thermodynamics by NMR -
10/27 13C basic principles 5.1
10/29 13C-decoupling 5.2
10/31 long weekend -
11/3 calculation of carbon chemical shifts 5.3
11/5 13C resonances for various functionality 5.3
11/7 same 5.3
11/10 problems -
11/12 problems -
11/14 2-D NMR theory 6.1 Quiz 3
11/17 2-D NMR techniques....... 6.2-5
11/19 - - EXAM 3 (in lab)
11/21 more 2-D techniques 6.5-6.9
11/24 spectral problems using 2D techniques 8
11/26 Thanksgiving -
11/28 Thanksgiving -
12/1 spectral problems using 2D techniques 8
12/3 spectral problems using 2D techniques 8
12/5 review -
12/8-12 f i n a l e x a m s
442 LAB SCHEDULE (FALL 2003)
Starting Experiment Reference Required
Date [points], (due date) Characterization
8/28 Check-in, Spectral Identification handout EIMS, CIMS, IR, 1HNMR
of an Unknown [40 points], (9/18)
9/4 as above
9/11 as above
9/17 Rxns of Alcohols handout IR, 1HNMR, 13CNMR, EIMS
(Wednesday) with Calcium
Hypochlorite [40 points],
9/25 Exam 1 - -
10/2 more Rxns of Alcohols….
10/9 as above
10/16 Experimental Smorgasbord@ handouts IR, 1HNMR, EIMS
[40 points], (12/4) COSY, DEPT
10/23 Exam 2 - -
10/30 more Smorgasbord
11/6 as above
11/13 as above
11/20 Exam 3 - -
11/27 Tgiving - -
12/4 Check-out - -
@ One from:
1. The Reaction of Cinnamyl Alcohol with Triethyl Orthoacetate
2. A View to Acrylate.
3. The Reaction of Oct-3-en-1-ol with Triethyl Orthoacetate
4. The Base-Induced Reaction of Salicylaldehyde with 1-Bromobutane in Acetone (2 versions)
5. The Reaction of Tetrahydrofuran with Acetyl Bromide.
details will follow..........
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