Chem 333
Fall 2009
Professor Joseph M. Fox
272 Brown Labs
302-831-0191
jmfox@udel.edu
Lectures are held in 101 Brown, Mondays 3:35–5:35 pm
Labs are held in Rm 318 Drake
Office hours: Mondays 11-12, or by
appointment.
Contact me by email to schedule an appointment
Teaching Assistants for
this course
Anthony Doellman, doelant@UDel.Edu
Ram Selvaraj, rams@udel.edu
Gabriela Uceda, guceda@UDel.Edu
Sections for
this course
Section 021: TA=Doellman, Monday, 7:00PM - 10:00PM QDH318
Section 022: TA=Ram, Tuesday, 12:30PM - 3:30PM QDH318
Section 024: TA=Uceda, Wednesday, 12:20PM - 3:20PM QDH318
Section 025, TA= Ram, Wednesday, 7:00PM - 10:00PM QDH318
Section 028: TA=Uceda, Thursday, 12:30PM - 3:30PM QDH318
Safety
You Must Have Safety Goggles
No Shorts
No Open Toed Shoes
No Food or Drink
Come Prepared, Read the Assignment, and Bring your Notebook
Textbooks:
For students taking both lab and lecture: Organic
Chemistry Laboratory, Third Edition by Bell,
Clark and Taber
For students taking only the lecture: Organic
Spectroscopic Structure Determination, by Taber
Grading and Exams:
Grading
for
the lecture part of this course will be determined based on
the average (50% each) of a midterm and final exam.
Midterm will be in class on October 26
Final will be in class on December 7
Chemical
Database Searching Tutorials
• Intro to Beilstein Handout
<>The following handouts demonstrate how to do more advanced
searches with Beilstein. Although they show the old Beilstein
interface, the concepts are the same with the new interface.
• Handout:
Introduction
to substructure
searching on Beilstein
Commander
• Handout:
Introduction to Reaction searching with substructures on Beilstein
commander
NOTE: Information about the lab is given after the information on the
lecture
portion of this course
Lecture schedule
Lecture 1 (9/14): Introduction
to
Structure
Determination by Spectroscopy; IHD and 13C NMR
spectroscopy.
READ: Chapter 12 in Bell, Clark and Taber or Chapter 1 in Organic
Spectroscopic Structure Determination
HANDOUT: 13C
LECTURE NOTES, 13C
NMR
TABLES
PROBLEMS: Complete end of chapter
12
problems 1–10 from Bell,
Clark and Taber
Answers
Lecture 2 (9/21): Problem Solving with 13C
NMR
spectroscopy
PROBLEMS: Complete end of
chapter 12 problems 11–20 from
Bell, Clark and Taber
Answers
Lecture 3 (9/28): 1H NMR
spectroscopy
READ: Chapter 13 in Bell,
Clark and Taber or
Chapter 2 in Organic Spectroscopic Structure
Determination
HANDOUT: 1H NMR Lecture guide
, 1H NMR
tables
PROBLEMS: Complete end of chapter 13
problems 1–10 from Bell,
Clark and Taber
Answers
Ans
Lecture 4 (10/5): Problem
Solving
with
1H
NMR spectroscopy
PROBLEMS: Complete end of
chapter 14 problems 1–5 from Bell,
Clark and Taber
Answers
HANDOUT: Structure
solving guide
Lecture 5 (10/12): Problem
Solving
with
1H
NMR spectroscopy
PROBLEMS: Complete end of
chapter 14 problems 6–10 from Bell,
Clark and Taber
Answers
Lecture 6 (10/19): more Problem
Solving with 1H
NMR spectroscopy, midterm review
MIDTERM EXAM (10/26)
refer back to Dr. Koh's website for old midterms
Lecture 7 (11/2): IR spectroscopy
HANDOUT: 1) IR lecture guide, 2)
handout: combined tables for
NMR, UV, IR and MS
PROBLEMS: IR problemset (answers combined with UV
problems)
Lecture 8 (11/9): Mass spectrometry
HANDOUT: MS Lecture notes
Lecture 9 (11/16): UV-vis spectroscopy
HANDOUT: 1) UV-vis Lecture notes
HOMEWORK: problemset and answers
Lecture 10 (11/23): 2-dimensional NMR and
advanced NMR techniques
HANDOUT: 2D NMR handout
HOMEWORK: 2D NMR problemset and answers
Lecture 11 (11/30): Problem solving with
multiple techniques; review for final
Review questions for the final
Final Exam (12/7): The final
exam will be given in class
The Laboratory
Goggles are required and must be worn
at all times in
the laboratory. Suitable clothing must also be worn.
Lab 1, week of Sept 14: Check in, Preparation of Anthranilic Acid (Read
Ch 1, 2, 3)
Handout
Lab 2, week of Sept 21: Extraction (Ch 4)
Handout
Lab 3: week of Sept 28, Distilation and GC (Ch 5 and 6)
Handout
Lab 4: week of Oct 5, Steam Distillation of Essential Oils
Handout
Lab 5: week of Oct 12, Complete Lab 4 and Chemical Database Searching
Handout
Lab 6: week of Oct 19, HPLC and TLC analysis of analgesics (Ch 8 and
9)
Handout
Lab 7: week of Oct 26, Column Chromatography, Caffeine from tea (Ch
7)
Handout
Lab 8: week of Nov 2, Oxidation/reduction of 4-nitrobenzyl alcohol
(Ch 21)
Handout
Lab 9: week of Nov 9, Wittig reaction and chemiluminescence
Handout
Lab 10: week of Nov 16, Grignard reaction: Preparation of Dyes (Ch
19)
Handout
NO LAB DURING WEEK OF NOV 23
Lab 12: week of Nov 30, Diels Alder reaction and checkout
Handout