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chem220b_S12

 Chem 220b, Section 01Organic Chemistry Lecture

Spring 2012

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 Wed., May 2, 2012 from 9:00 – 11:00 am (CST) in SC 4309.

There will be NO alternative date offered.

Office hours for finals week will be:

Tue., 4/24 – Tue., 5/01: 1:00 – 2:30 pm

Course Syllabus

Updated : 04/13/2012

Links to C. J. Rizzo’s Chem 220a from Fall 2010 or Chem 220b from Spring 2008 and Chem 220b from Spring 2011 pages

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 02/06/2012)

 

Required text: Organic Chemistry, 8th edition, Francis A. Carey & Robert M. Giuliano (ISBN 978-0-07-340261-1)

Optional text: Student Solutions Manual to Accompany Organic Chemistry, Neil T. Allison et al. (ISBN 978-0-07-329397-4)

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

The text (Carey & Giuliano) and study guide (Allison et al.) have been bundled by the bookstore at a discounted price

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

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 13, 15-26 of Carey & Giuliano. 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: 9:00-10:00, 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.

Recitation Session: You should be enrolled in a weekly recitation section. Recitation is 10% of the overall grade (50 points) and will be comprised of particpation in weekly workshops (5%) and quizzes (best 4 of 5, 5%). There will be no make-up quizzes. Prof. G. Sulikowski is in charge of the recitations. See below for the recitation schedule.

Course Policies:

Exams: Three in-class exams (100 pts each), one two-hour final exam (150 pts), and recitation (50 points).

Exam dates are indicated on the schedule below and will NOT be changed. Hour exams 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: Three in-class exams (60% of final grade), recitation (10 % of final grade) and one two-hour final exam (30% 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.

“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

 Tue  Jan 10  Chapter 13: Spectroscopy  Problems (Carey & Giuliano): 3-20, 22-26, 30-37, 39, 40, 43, 44, 46, 51-60

 slides for Chapter 13: slides #1-73 (pdf / ppt) (updated 01/18/2012)

 Thur  Jan 12  Chapter 13 (con’t)  Typical IR absorptions and NMR chemical shifts.
 Tue  Jan 17  Chapter 13 (con’t)
 Thur  Jan 19  Chapter 13 (con’t)
 Tue  Jan 24  Chapter 15: Alcohols, Diols, & Thiols

 

 Problems (Carey & Giuliano): 1-5, 7-11, 14-16, 18-28, 30-33, 36, 38-41

 slides for Chapter 15: slides #74-96 (pdf / ppt) (01/19/2012)

 Thur  Jan 26  Chapter 15 (con’t)
 Tue  Jan 31  Chapter 16: Ethers, Epoxides, and Sulfides  Problems (Carey & Giuliano): 1, 3, 5-10, 12-17, 21, 25-29, 32, 34, 35, 40-43

 slides for Chapter 16: slides #97-114 (pdf / ppt) (01/25/2012)

 Thur  Feb 2  Chapter 17: Aldehydes & Ketones  Problems (Carey & Giuliano): 1-7, 10-14, 16-22, 26-29, 31-35, 37, 39-42, 44, 46-55

 slides for Chapter 17: slides # 115-143 (pdf / ppt) (updated 02/28/2012)

 Tue  Feb 7  Exam 1  Exam 1 answers / distribution  Chapters 13, 15, & 16
 Thur  Feb 9  Chapter 17: Aldehydes & Ketones (con’t)  Chapter 5 (Ketones and Aldehydes) of Organic Chemistry II by Klein

Curved Arrow Convention

 Tue  Feb 14  Chapter 18: Carboxylic Acids  Problems (Carey & Giuliano): 1-3, 5, 7-9,11-17,19-26, 28, 29, 31-33

 slides for Chapter 18: slides # 144-161 (pdf / ppt) (updated 02/28/2012)

 Thur  Feb 16   Chapter 18 (con’t)  brief handout on drawing strructures: pdf / ppt (02/16/2011)
 Tue  Feb 21  Chapter 19: Carboxylic Acids Derivatives: Nucleophilic Acyl Substitution  Problems (Carey & Giuliano): 1-8, 10, 12-17, 20, 21, 24-29, 32, 33, 36-38, 40-42, 44, 45, 48-50

 slides for Chapter 19: slides # 162-188 (pdf / ppt) (updated 02/28/2012)

 Thur  Feb 23  Chapter 19 (con’t)  Chapter 6 (Carboxylic Acid Derivatives) of Organic Chemistry II by Klein
 Tue  Feb 28  Chapter 19 (con’t)
 Thur  Mar 1  Exam 2  Exam 2 answers / distribution   Chapters 13, 15 – 19
 Mar 3 – Mar 11  Spring Break (no classes)  Mid-semester progress reports due
 Tue  Mar 13  Chapter 20: Enols and Enolates  Problems (Carey & Giuliano): 1-5, 7-24, 26, 27, 29-36, 38, 39, 41-44, 46-48, 51, 53-56, 58, 59-64, 69, 74, 75, 79, 80, 82-84

 slides for Chapter 20: slides # 189-225 (pdf / ppt) (updated 03/15/2012)

 Thur  Mar 15  Chapter 20 (con’t)  Chapter 7 (Enols and Enolates) of Organic Chemistry II by Klein

 Review Chapter 13 (Synthesis) of Organic Chemistry I by Klein

 Tue  Mar 20  Chapter 21: Amines  Problems (Carey & Giuliano): 1-7, 11-16, 18-25, 27-29, 33-40, 43-46, 48, 50, 53, 55, 56

 slides for Chapter 21: slides # 126-250 (pdf / ppt) (updated 03/20/2012)

 Chapter 8 (Amines) of Organic Chemistry II by Klein

 Thur  Mar 22  Chapter 22: Phenols

 

 Problems (Carey & Giuliano): 1, 3, 6-9, 12-17, 19-26, 36

 slides for Chapter 22: slides #251-262 (pdf / ppt) (03/16/2012)

 Tue  Mar 27  Chapter 23: Carbohydrates  Problems (Carey & Giuliano): 1-9, 12-20, 21, 22, 23, 26-30, 32-36, 38, 42

 slides for Chapter 23: slides #263-297 (pdf / ppt) (03/21/2012)

 Thur  Mar 29  Chapter 23 (con’t)  Brief Review of Stereochemistry

Fischer Projections

 Tue  Apr 3  Chapter 23 (con’t)  Review Chapter 7 (Configurations) of Organic Chemistry I by Klein
 Thur  Apr 5  EXAM 3 Exam 3 answers / distribution  Chapters 13, 15 -23
 Tue  Apr 10  Chapter 24: Lipids  Problems (Carey & Giuliano): 1, 3-5, 7, 9-12, 18, 20, 23-25, 28, 32

 slides for Chapter 24: slides #298-324 (pdf / ppt) (04/09/2012)

 Thur  Apr 12  Chapter 25: Amino Acids, Peptides, and Proteins  Problems (Carey & Giuliano): 1-7, 11-14, 17-25, 28, 29, 31, 34-37,40, 42, 43, 45

 slides for Chapter 25: slides #325-357 (pdf / ppt) (04/09/2012)

 Tue  Apr 17  Chapter 25 (con’t)
 Thur  Apr 19  Chapter 26: Nucleosides, Nucleotides, and Nucleic Acids  Problems (Carey & Giuliano): 1, 2, 4-6, 11, 13-16, 19, 21, 25,

 slides for Chapter 26: slides #358-382 (pdf / ppt) (04/13/2012)

 Wed  May 2  Final Exam (9:00 – 11:00 pm)  Chapters 13, 15-26
Tentative Recitation Schedule
week of:
Workshop Topic
 Jan 9  no recitation
 Jan 16  no recitation
 Jan 23  Spectroscopy (QUIZ 1)
 Jan 30  Alcohols & Diols
 Feb 6  Ethers, Epoxides (QUIZ 2)
 Feb 13  Aldehydes & Ketones
 Feb 20  Carboxylic Acids (QUIZ 3)
 Feb 27  Carboxylic Acid Derivatives
 Mar 5  Spring break
 Mar 12  Mechanism / Synthesis Review
 Mar 19  Enols & Enolates
 Mar 26  Amines (QUIZ 4)
 Apr 2  Carbohydrates
 Apr 9  Lipids (QUIZ 5)
 Apr 16  Amino Acids & Proteins
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