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chem220b_S11

 Chem 220b, Section 01Organic Chemistry Lecture

Spring 2011

T, R 9:35-10:50 am

Room 4309, SC Lecture Halls

 Carmelo J. Rizzo

office: Rm 7662, SC New Chemistry Bldg

Tel.: 322-6100

e-mail: c.j.rizzo@vanderbilt.edu

The Final Exam is scheduled for Tue., May 3, 2011 from 3-5 pm (CST) in SC 4309.

There will be NO alternative date offered.

Office hours for finals week will be:

Wed. (4/27): 8:00 – 9:30 am (normal hrs);

Thur. (4/28): 11:00 – 12:00 and 1:00 – 2:30 pm

Fri. (4/29): 10:30 – 11:45

Mon. (5/02): 1:00 – 2:30 pm

 

Updated : 05/02/2011

Links to C. J. Rizzo’s Chem 220a page or Chem 220b from Spring 2008.

You will need Adobe Acobat Reader to view pdf files.

 

Questions & Answers Page: I am posting questions and answers from the class, sent to me via email. Updated (05/02/2011)

 

Required text: Organic Chemistry, 4th edition, Maitland Jones, Jr. & Steven A, Fleming (ISBN 978-0-393-93149-5)

Optional text: Student Solutions Manual to Accompany Organic Chemistry

Organic Chemistry as a Second Language, 2nd Edition, David R. Klein (ISBN 978-0-471-73808-4)

The text and study guide have been bundled by the bookstore.

You should be concurrently enrolled in Organic Chemistry Laboratory (Chem 219b) which is taught by Professor P. Kaszynski. Please direct all question regarding the lab to Professor Kaszynski.

Molecular Models: Organic chemistry is a three dimensional science. Molecular models are highly recommended for lecture and may be purchased from the Student Affiliates of the American Chemical Society:

Organic Chemistry Models (Molecular Design, Inc.)

or from the Bookstore:

HGS Molecular Structure Models

Course Content: Chapters 12-19, 22, 23 of Jones & Fleming. A tentative schedule of topics is listed below. Chapters covered on the hour exams and Final may be adjusted if we fall behind schedule; the exams will never cover more than is stated.

Office Hours: M: 1:00-2:00, T: 11:00-12:00, W: 8:00-9:30, Th: 11:00-12:00. Office hours are subject to change or cancellation without prior announcement. E-mail is an excellent way to communicate with me.

Weekly Review Session: Monday and Tuesday from 5:00-6:00 om in room SC 5502 (5th floor of the Science & Engineering Bldg).

Course Policies:

Exams & Quizzes: Three hour exams (100 pts each), four quizzes (100 pts total), ~10 weekly on-line quizzes (25 pts total), and one two-hour final exam (200 pts). Quiz grades toward the overall average will be the best 4 out of 5 (4 inclass and total of the weekly quizzes). The online quizzes will be accessed through the SmarkWork system that comes with your textbook (see announcement posted on OAK for the enrollment key). The quizzes will be open for ~two days and may be accessed only once. My expectation is that you will work alone on these online quizzes. You may use you book and notes.

Exam and quiz dates are indicated on the schedule below and will NOT be changed. Hour exams and quizzes will be given during the regularly scheduled class time.

Final Exam: The final exam date is Tue., May 3 2011 from 3-5 pm (CST). There will be NO alternative date offered. Please make your travel plans accordingly.

Grades: Exams & quizzes (~67 % of final grade); Two-hour final Exam (~33% of final grade)

Your final grade will be determined by your overall average. Assignng letter grades will start with scale shown below; the ranges may be expanded according to the class distribution.
90-100= A range; 80-89= B range; 70-79= C range; 60-69= D range; below 60= F

Make Up Exams: I will give make-up exams under the following conditions:

1. If it can be made up within 24 hrs of the missed exam.
2. If it is arranged prior to the day of the missed exam.
3. There is a legitimate medical or family excuse. These excuses must be verified in writing by the Dean’s office for family reasons or a physician for illness. A note stating that you visited Student Health is not sufficient. Having other exams on the same day nor anxiety attacks will not be considered.

If all three of these condition cannot be met and you have an excusable absence from the exam then your final exam will count for a proportionally larger portion of the total grade. It is to your advantage to take all exams. There will be no make-up quizzes.

A note on partial credit: Simply writing down an answer does not entitle you to partial credit. For partial credit to be awarded the answer must first, be at least partially correct; second, it must be relevant to the question being asked. Writing down the answer to a question that is not being asked does not warrant partial credit.

Handing back of exams and re-grades of exams: The goal is to have the exams graded and returned by the next scheduled class. Requests for re-grade will be considered for one week after the day the exams are handed back. DO NOT MAKE ANY MARKS ON THE EXAMS UNTIL YOU ARE SATISFIED WITH THE GRADING!!

Honor Pledge: You must legibly write the Vanderbilt Honor Pledge on the cover sheet of every exam and quiz. Writing the honor pledge acknowledges that you are committed to the Vanderbilt Honor Code. Examsand quizzes which do not have the honor pledge will not be graded and you will receive a zero.

“I pledge my honor that I have neither given nor received aid on this examination”

A Helpful Hint: There is a tremendous volume of information to be covered in this course and we will need to proceed at a brisk pace. I suggest that you come to class prepared, having already read the chapter. This will allow you to concentrate on concepts that may be unclear to you. Chemistry is a problem solving oriented subject, thus I suggest that you work through every problem in the chapters we cover (you may see some of them reappear on exams). Finally, come to class!! Important concepts, i.e. thing that may appear on exams, are emphasized in lecture as well as things not covered in the book. This course is challenging; be prepared to dedicate at least 1-2 hours per night (5-10 hrs/wk) on organic chemistry.

Review of Previous Material: It is assumed that you have mastered the first semester of Organic Chemistry (Chapters 1-11 of Jones & Fleming) as well as understand the vocabulary of organic chemistry. In addition to the material from Chem

Text: “Chemistry: A Molecular Approach”, Nivaldo J. Tro
Pearson Prentice Hall Publishing: 2008

Electronic Structure: Chapter 8
Lewis Structure and Chemical Bonds: Chapter 9
VSEPR and Molecular Orbitals: Chapter 10
Atomic Orbitals: Chapter 7
Chemical Equilibrium: Chapter 14
Acid-Base Equilibrium: Chapters 15 and 16
Thermochemistry: Chapters 6 and 17

As the course progresses there may be some important numbers and equations you will be expected to commit to memory. These will be explicitly pointed out to you. You should already know the following from General Chemistry.

The Gas Law Constant, R= 1.99 cals/(mol)(°K) (2.0 is close enough) -or- = 8.314 J/(mol)(°K)

Gibb’s Free Energy: ΔG°= ΔH° – TΔS°

ΔG°= -RT ln Keq

pKa= – log Ka

In addition, it is also assumed that you know the vocabulary of General Chemistry. That is, you should know the names, structures, and charges of the common anions (see Tables 3-3 and 3-5, pg. 94-95 of Tro) and the names and structures of common mineral acids (see Table 15.1, pg. 664 of Tro) and bases (see Table 15.2, pg. 666 of Tro)

 

Suggested Problems: Listed below are representative problems from each chapter. Organic Chemistry is a problem solving oriented course. It is suggested that you work all the problems in each chapter and more if possible. Working problems will enhance your ability to do well on exams.

Tentative Class Schedule

Dates

Chapter

 Suggested Problems, Comments, and Links to Slides and Handouts

 Thur  Jan 13  Chapter 12: Dienes and the Allyl System: 2p Orbitals in Conjugation  Problems (Jones & Fleming): 1-3, 8-10, 12-22, 24-27, 29, 30, 38, 40-46, 48, 49, 52, 53, 55, 61, 62, 63c-d.

 slides for Chapter 12 (#1-29): pdf / ppt (01/09/2011)

 Tue  Jan 18  Chapter 12 (con’t)  Curved Arrow Convention

 Review Chapters 2 (Resonance) and 3 (Mechanism) of Organic Chemistry I by Klein

 Thur  Jan 20  Chapter 15: Analytical Chemistry: Spectroscopy  Problems (Jones & Fleming): 3, 5, 7, 10-20, 22-27, 32-35, 37, 40-46, 48, 49, 51-55, 57, 60, 61, 64, 65, 73, 79, 91.

 slides for Chapter 15 (#30-86 ): pdf/ ppt (revised 01/25/2011)

  Tue  Jan 25  Chapter 15 (con’t)  Typical IR absorptions and NMR chemical shifts.
 Thur  Jan 27  Chapter 13: Conjugation and Aromaticity

 Quiz 1: Chapters 12 and 15.1-15.6c (~ page 750) – answers / distribution

 Problems (Jones & Fleming): 1, 7-10, 13, 16, 17, 19, 23, 24, 26-29, 31, 32, 34-40, 43-48, 51, 52, 54, 57, 58, 60

 slides for Chapter 13 (#87-115): pdf / ppt (revised 02/01/2011)

 Tue  Feb 1  Chapter 13 (con’t)
 Thur  Feb 3  EXAM 1: Chapters 12, 15, 13.1-13.9 – answers / distribution
 Tue  Feb 8  Chapter 14: Substitution Reactions of Aromatic Compounds  Problems (Jones & Fleming): 1, 2, 4-11, 13-17, 19-21, 26-32, 34-37, 45-51, 54-58, 60, 61, 63, 71.

 slides for Chapter 14 (#116-143): pdf / ppt (updated 02/09/2011)

 Thur  Feb 10  Chapter 14 (con’t)  summary of electrophilic aromatic substitution (revised 02/11/2011)

 Chapter 3 (Electrophilic Aromatic Substitution) and 4 (Nucleophilic Aromatic Substitution) of Organic Chemistry II by Klein

 Tue  Feb 15  Chapter 16: Carbonyl Chemistry 1: Addition Reactions   Problems (Jones & Fleming): 8, 9, 11-22, 24-29, 31-49, 57, 59, 62, 63, 65, 67, 69-73.

  slides for Chapter 16 (#144-175): pdf / ppt (revised 02/24/2011)

 Thur  Feb 17  Chapter 16 (con’t)

 Quiz 2: Chapters 14answers / distribution

 Chapter 5 (Ketones and Aldehydes) of Organic Chemistry II by Klein
 Tue  Feb 22   Chapter 16 (con’t)  brief handout on drawing strructures: pdf / ppt (02/16/2011)
 Thur  Feb 24  Chapter 17: Carboxylic Acids  Problems (Jones & Fleming): 1, 2, 4, 6, 7, 9-11, 13-17, 21-23, 25-36, 37-39, 41, 43, 44, 46, 49b, 49d, 50, 53, 55.

 slides for Chapter 17 (#176-198 ) pdf / ppt (updated 02/28/2011)

 Tue  Mar 1  Exam 2: Chapters 12-16answers / distribution
 Thur  Mar 3  Chapter 17 (con’t)  Chapter 6 (Carboxylic Acid Derivatives) of Organic Chemistry II by Klein
 Mar 5 – Mar 12  Spring Break (no classes)  Mid-semester progress reports due
 Tue  Mar 15  Chapter 17 (con’t)
 Thur  Mar 17  Chapter 18: Derivatives of Carboxylic Acids: Acyl Compounds  Problems (Jones & Fleming): 1, 2, 4-13, 16, 17, 19-23, 26, 29, 33-40, 42, 45, 47-51

 slides for Chapter 18 (#199-221 ) pdf / ppt (updated 03/11/2011)

 Tue  Mar 22  Chapter 18 (con’t)
 Thur  Mar 24  Chapter 19: Carbonyl Chemistry 2: Reactions at the α-Position

 Quiz 3: Chapters 17 -18answers / distribution

 Problems (Jones & Fleming): 1-5, 7-21, 23-29, 31-35a, 36, 38, 47-57, 59, 60, 62-65, 67, 70-75

 slides for Chapter 19 (#222-257) pdf / ppt (revised 03/21/2011)

 Tue  Mar 29  Chapter 19 (con’t)  Chapter 7 (Enols and Enolates) of Organic Chemistry II by Klein
 Thur  Mar 31  Chapter 19 (con’t)
 Tue  Apr 5  EXAM 3: Chapters 12-19 answers / distribution
 Thur  Apr 7  Chapter 22: Carbohydrates  Problems (Jones & Fleming): 1-17, 20-24, 26-38, 41, 42, 49

 slides for Chapter 22 (#258-292) pdf / ppt (revised 04/18/2011)

 Tue  Apr 12  Chapter 22 (con’t)  Brief Review of Stereochemistry Fischer Projections
 Thur  Apr 14  Chapter 22 (con’t)

 Quiz 4: 12-19, 22 answers / distribution

 Tue  Apr 19   Chapter 23: Amino Acids and Polyamino Acids (Peptides and Proteins)  Problems (Jones & Fleming): 1-7, 9-13, 15-19, 21, 23, 23-32, 35-37, 41

 slides for Chapter 23 (#293-335) pdf / ppt (revised 04/25/2011)

 Thur  Apr 21  Chapter 23 (con’t)
 Tue  Apr. 26  Chapter 23 (con’t)
 Tue  May 3  Final Exam (3:00 – 5:00 pm)  Chapters 12-19, 22, 23

Exams from 2006 (Text: McMurray, Organic Chemistry. 6th ed)

 Exam 1

 Exam 2

 Exam 3

Some Useful Links

Organic Chemistry OnLine Tutorial Chemistry ConcepTests
Web-sters Organic Chemistry Univ. of Colorado NMR/IR Spectroscopy Tutorial
IUPAC Nomenclature of Organic Chemistry Organic Chemistry Practice Problems
 UCLA Organic Chemistry Tutorials  Colby College Organic Chemistry Resource Page
Electronic Flashcards of Organic Reactions Virtual Textbook of Organic Chemistry
Organic Chemistry Help!!  Organic Reactions: Movies
OCHeM.com