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Chem 220b

 Chem 220b, Section 01Organic Chemistry Lecture

Spring 2015

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 Thur., April 23, 2015 from 3:00 – 5:00 pm (CST) in SC 4309.

There will be NO alternative date offered.

Office hours for finals week will be:

Fri., 4/17: 11:00 am – noon

Mon., 4/20 : 11:00 am – noon and 1:00 – 2:00 pm

Tue, 4/21 : 11:00 am – 1:00 pm

Wed. 4/22 : 1:00 am – noon and 1:00 – 2:00 pm

Course Syllabus

Updated : 04/18/2015

Links to C. J. Rizzo’s Chem 220a (Fall 2010) or Chem 220b (Spring 2012) 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 02/25/2015)

 

Required text: Organic Chemistry, 9th edition, Francis A. Carey & Robert M. Giuliano (ISBN 978-0-07-340274-1)

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, 3rd edition, David R. Klein (ISBN 978-1-118-14434-3)

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: 10:00-11:00, 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 5% of the overall grade and will be comprised of particpation in weekly workshops and Sapling homework. Prof. M. Sulikowski is the recitation coordinator. See below for the recitation schedule.

Course Policies:

Exams: Three in-class exams (100 pts each), one two-hour final exam (175 pts), and recitation (25 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 Thur., April 23, 2015 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 & Sapling homework (5% of final grade) and one two-hour final exam (35% 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. I prefer the
excuses 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.

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 be at least partially correct and 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 returned. 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 on 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
1-12 and 14 of Carey & Giuliano) as well as understand the vocabulary of organic
chemistry. In addition to the material from General Chemistry.

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 6  Chapter 13: Spectroscopy  Summary of course policies

Problems (Carey & Giuliano): 3-14, 16-21, 23-37, 39, 43-46, 48, 51-53

 slides for Chapter 13: slides #1-73 (updated 1/19/2014)

 Thur  Jan 8  Chapter 13 (con’t)  Klein – Organic Chemistry II: Chapters 1 (IR) and 2 (NMR)
 Tue  Jan 13  Chapter 13 (con’t)  Typical IR absorptions and NMR chemical shifts. (updated 1/19/2014)
 Thur  Jan 15  Chapter 13 (con’t)  combined spectra problems
 Tue  Jan 20  Chapter 15: Alcohols, Diols, & Thiols

 

 Problems (Carey & Giuliano): 1-5, 7-10, 13-27, 28-31, 34, 36-39

 slides for Chapter 15: slides #74-96 (12/31/2014)

 Thur  Jan 22  Chapter 15 (con’t)  Klein – Organic Chemistry I: Chapter 12 (Alcohols)

brief handout on drawing strructures (updated 02/16/2011)

 Tue  Jan 27  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 (01/02/2015)

 Thur  Jan 29  Chapter 17: Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group  Problems (Carey & Giuliano): 1-7, 10-14, 17-22, 24, 26-29, 31-35, 37, 39-42, 44, 46-55

 slides for Chapter 17: slides #115-143 (updated 02/11/2015)

 Tue  Feb 3  Exam 1  (answersdistribution)  Chapters 13, 15, & 16
 Thur  Feb 5  Chapter 17 (con’t)  Klein – Organic Chemistry II: Chapter 5 (Ketones and Aldehydes)

Curved Arrow Convention

 Tue  Feb 10  Chapter 18: Carboxylic Acids  Problems (Carey & Giuliano): 1-3, 5, 7-17,19-26, 28, 29, 31-33

 slides for Chapter 18: slides #144-161 (02/03/2015)

 Thur  Feb 12   Chapter 18 (con’t)
 Tue  Feb 17  Chapter 19: Carboxylic Acids Derivatives: Nucleophilic Acyl Substitution  Problems (Carey & Giuliano): 1-7, 9, 11-16, 19-22, 24-29, 32, 33, 37, 38, 40-42, 44, 45, 47-49

 slides for Chapter 19: slides #162-187 (02/09/2015)

 Thur  Feb 19  Chapter 19 (con’t)  Klein – Organic Chemistry II: Chapter 6 (Carboxylic Acid Derivatives)
 Tue  Feb 24  Chapter 19 (con’t)
 Thur  Feb 26  Exam 2  (answersdistribution)   Chapters 13, 15 – 19
 Mar 1 – Mar 8  Spring Break (no classes)  Mid-semester progress reports due
 Tue  Mar 10  Chapter 20: Enols and Enolates  Problems (Carey & Giuliano): 1-23, 25-30, 34, 36-45, 47-54, 57

 slides for Chapter 20: slides #188-222 (02/23/2015)

 Thur  Mar 12  Chapter 20 (con’t)  Klein – Organic Chemistry II: Chapter 7 (Enols and Enolates)

 Review Klein – Organic Chemistry I: Chapter 13 (Synthesis)

 Tue  Mar 17  Chapter 21: Amines  Problems (Carey & Giuliano): 1-7, 10-16, 18-25, 27-29, 33-40, 43-46, 48-51, 53, 55, 56

 slides for Chapter 21: slides #223-248 (03/10/2015)

 Klein – Organic Chemistry II: Chapter 8 (Amines)

 Thur  Mar 19  Chapter 22: Phenols

 

 Problems (Carey & Giuliano): 1, 3, 4, 6-9, 12-17, 19-26, 36

 slides for Chapter 22: slides #249-260 (03/10/2015)

 Tue  Mar 24  Chapter 23: Carbohydrates  Problems (Carey & Giuliano): 1-9, 11-20, 22, 24, 26-34, 36, 38, 42, 43, 45-49

 slides for Chapter 23: slides #261-295 (updated 03/30/2015)

 Thur  Mar 26  Chapter 23 (con’t)  Brief Review of Stereochemistry

Fischer Projections

 Tue  Mar 31  Chapter 23 (con’t)  Review Klein – Organic Chemistry I: Chapter 7 (Configurations)
 Thur  Apr 2  EXAM 3 (answers distribution)  Chapters 13, 15 -23
 Tue  Apr 7  Chapter 24: Lipids  Problems (Carey & Giuliano): 1, 3, 5, 7-10, 16, 18, 22, 23, 26, 30

 slides for Chapter 24: slides #296-322 (updated 03/31/2015)

 Thur  Apr 9  Chapter 25: Amino Acids, Peptides, and Proteins  Problems (Carey & Giuliano): 1-9, 13, 14, 18-24, 27, 30, 33-36, 39, 41, 42, 44

 slides for Chapter 25: slides #323-357 (03/20/2015)

 Tue  Apr 14  Chapter 25 (con’t)
 Thur  Apr 16  Chapter 26: Nucleosides, Nucleotides, and Nucleic Acids  Problems (Carey & Giuliano): 1-6, 8, 11, 13-16, 19, 21, 25,

 slides for Chapter 26: slides #358-382 (03/20/2015)

 Thur  Apr 23  Final Exam (3:00 – 5:00 pm)  Chapters 13, 15-26
Tentative Recitation Schedule
week of:
Topic
 Jan 4  Formulas from mass spectra and IR
 Jan 11  NMR
 Jan 18  no recitation
 Jan 25  Alcohols
 Feb 1  no recitation
 Feb 8  Carbonyls
 Feb 15  Carboxylic Acids
 Feb 22  Carboxylic Acid Derivatives
 Mar 1  Spring break – no recitation
 Mar 8  no recitation
 Mar 15  Enols & Enolates
 Mar 22  Amines
 Mar 29  Carbohydrates
 Apr 5  no recitation
 Apr 12  Amino Acids
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
AceOrganicChem.com Organic Reactions: Movies
OCHeM.com