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Chem2211f2017

Chem2211F2017

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Chem 2211-01:

Organic Chemistry for Advanced Placement Students

   

Fall 2017
M, W, F 10:10-11:00 am
Room SC 5211

Carmelo J. Rizzo

office: Rm 7662, SC New Chemistry Bldg

Tel.: 322-6100

Course Syllabus

Updated : 11/01/2017
Links to C. J. Rizzo’s Chem 2211 (Fall 2016) or Chem 220b (Spring 2015) 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.
Required text: Organic Chemistry, 2nd edition, David R. Klein (ISBN: 978-1-118-45228-8) (Errata Sheet for Klein, Organic Chemistry 2e, updated 11/26/14)
Optional text: Student Study Guide and Solutions Manual to accompany Organic Chemistry, David R. Klein (ISBN: 978-1-118-64795-0)
A custom bundle containing the binder version of the text, enhanced etext (etext + esolutions manual), is available in the bookstore ($267.15).
Also highly recommended is “Practice Organic Mechanisms” workbook by M. Sulikowski & J. A. Ashenhurst. The book can be purchased from Dr. Silikowski (SC 7660) or ordered on-line for $20.

Lab: You should be concurrently enrolled in Organic Chemistry Laboratory (Chem 2211L) 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 1-14 and 27 of Klien. 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. The schedule will have links to lecture slides and other handouts. Additional course material will be uploaded to the course folder on Box. You must accept an invitation to share the contents of the class Box folder. The box login page is: https://vanderbilt.account.box.com/login.

Office Hours: M: 1:00 pm – 2:00 pm, T: 1:00 pm – 2:00 pm, W: 2:00 pm – 3:00 pm, Th: 11:00 am – 12:00 noon and by appointment. Office hours are subject to change or cancellation without prior announcement. E-mail is an excellent way to communicate with me. I have also reserved Commons room 335 from 5:30 – 6:30 on Monday evening.

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. Prof. M. Sulikowski is the recitation coordinator. See below for the recitation schedule.

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 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)

Tutoring: Tutoring from from peers and graduate students is available from the Tutoring Service.

Course Policies

Exams: Three in-class exams (100 pts each) and one two-hour final exam (175 pts)

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 Mon., Dec. 11, 2016 from 9:00-11:00 am (CST). No alternate final exam date will be offered, so please make you travel plans accordingly.

Grades: Three in-class exams (60 % of final grade), one two-hour final exam (35% of final grade), and recitation (5% of final grade)

Your final grade will be determined by your overall average. Assigning letter grades will start with the 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. Exams and quizzes that do not have the honor pledge will not be graded.

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

   

Tentative Class Schedule

Suggested Problems: Listed below are representative problems from each chapter of Klein. 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.

Dates

Chapter

Suggested Problems, Comments, and Links to Slides and Handouts

Wed Aug 23 Chapter 1: A Review of General Chemistry: Electrons, Bonds, and Molecular Properties Summary of course policies (updated 8/22/2017)

Problems: 1-6, 8-10, 12-30, 34-36, 38-43, 46-50, 53, 55, 59, 63, 65, 67
slides for Chapter 1: slides 1-26 (revised 8/18/2015)

Fri Aug 25 Chapter 1 (con’t)
Mon Aug 28 Chapter 2: Molecular Representations Problems: 1-5, 8, 9, 11-14, 16-19, 21-28, 32-36, 40-42, 44, 45, 47-49, 51, 55, 56-58, 60, 61, 73, 77
slides for Chapter 2: slides 27-42 (8/20/2015)
Wed Aug 30 Chapter 2 (con’t) Curved Arrow Convention
Fri Sept 1 Chapter 3: Acids & Bases Problems: 1-4, 7-15, 18-20, 23, 25, 26, 29, 31, 34-41, 44-52, 54, 62
slides for Chapter 3: slides 43-51 (revised 9/05/2015)
Mon Sept 4 Chapter 3 (con’t)
Wed Sept 6 Chapter 4: Alkanes and Cycloalkanes Problems: 1-3, 5-8, 10, 11, 14-33, 36-43, 45-48, 50-61, 63, 66, 68
slides for Chapter 4: slides 52-92 (revised 09/14/2015)
Fri Sept 8 Chapter 4 (con’t) brief handout on drawing structures
Mon Sept 11 Chapter 4 (con’t)
Wed Sept 13 Chapter 5: Stereoisomerism Problems: 1-7, 9-22, 25-32, 34b, 35-47, 49, 51, 53, 55-57
slides for Chapter 5: slides 93-117
Fri Sept 15 EXAM 1 Chapter 1-4
Mon Sept 18 Chapter 5 (con’t) Brief Review of Stereochemistry
Wed Sept 20 Chapter 5 (con’t) Fischer Projections
Fri Sept 22 Chapter 6: Chemical Reactivity and Mechanism Problems: 1-3, 6-14, 16-24, 26-31, 36, 39, 40, 43-49, 53, 60, 61
slides for Chapter 6: slides 118-138 (revised, 10/01/2015)
Mon Sept 25 Chapter 6 (con’t)
Wed Sept 27 Chapter 6 (con’t)
Fri Sept 29 Chapter 7: Substitution Reactions Problems: 1-10, 13-16, 18-27, 29, 31-34, 36-55, 57-67, 69, 77,
slides for Chapter 7: slides 139-165 (updated, 10/08/2015)
Mon Oct 2 Chapter 7 (con’t) summary of nucleophilic substitution (revised 10/07/2015)
Wed Oct 4 Chapter 7 (con’t)
Fri Oct 6 EXAM 2 Chapters 1-7
Mon Oct 9 Chapter 8: Alkenes: Structure and Preparation via Elimination Reactions Problems: 1, 2, 4, 5, 7-22, 27-39, 41-44, 46-52, 54-71, 73-79, 81-84, 87
slides for Chapter 8: slides 166-189 (updated, 10/15/2015)
Wed Oct 11 Chapter 8 (con’t)
Oct 12 – Oct 13 Fall Break (no classes) Mid-semester progress reports due
Mon Oct 16 Chapter 8 (con’t)
Wed Oct 18 Chapter 9: Addition Reactions of Alkenes Problems: 1-23, 25-28, 30-43, 45-+47, 49-58, 60-65, 67-71, 74, 79, 81-82
slides for Chapter 9: slides 190-212 (updated 10/25/2015)
Fri Oct 20 Chapter 9 (con’t) Summary of addition reactions to alkenes
Mon Oct 23 Chapter 9 (con’t)
Wed Oct 25 Chapter 10: Alkynes Problems: 1-7, 9-16, 18-32, 34-48, 51-57, 59-62, 65
slides for Chapter 10: slides 213-228 (revised 10/20/2017)
Fri Oct 27 Chapter 10 (con’t) Summary of addition reactions to alkynes
Related reactions of alkenes and alkynes
Mon Oct 30 Chapter 10 (con’t)
Wed Nov 1 Chapter 11: Radical Reactions Problems: 1-17, 20-28, 31-36, 38-41, 43-45
slides for Chapter 11: slides 229-246 (updated 11/01/2017)
Fri Nov 3 Chapter 11 (con’t)
Mon Nov 6 Chapter 11 (con’t)
Wed Nov 8 EXAM 3 Chapter 1-11
Fri Nov 10 Chapter 12: Synthesis Problems: 1-27, 29, 30, 36, 37
slides for Chapter 12: slides 247-252 (11/14/2015)
Some Synthesis Problems
Mon Nov 13 Chapter 13: Alcohols and Phenols Problems: 1, 2, 4-52, 58, 59
slides for Chapter 13: slides 253-278 (updated, 11/22/2015)
Wed Nov 15 Chapter 13 (con’t)
Fri Nov 17 Chapter 13 (con’t)
Nov 18 – Nov 26 Thanksgiving Break (no classes)
Mon Nov 27 Chapter 14: Ethers and Epoxides; Thiols and Sulfides Problems: 1-3, 5, 6, 8-15, 17-26, 30-33, 35, 37-44, 47-51, 59, 60
Wed Nov 29 Chapter 14 (con’t) slides for Chapter 14: slides 279-295 (11/29/2015)
Fri Dec 1 Chapter 27: Synthetic Polymers Problems: 1-7, 9, 13, 19, 22, 24-26, 37, 39
slides for Chapter 27: slides 296-310
Mon Dec 4 Chapter 27 (con’t)
Wed Dec 6
Mon. Dec 11, 9-11 am Final Exam Chapters 1-14, 27

Tentative Recitation Schedule

week of:
Topic
Aug 23 no recitation
Aug 28 Chapters 1-2: VSEPR review, hybridization, resonance
Sept 4 Chapter 3: ARIO, acid/base review
Sept 11 Chapter 4: Newman projections, conformational analysis
Sept 18 Chapter 5: Stereoisomerism (bring model kits)
Sept 25 Chapter 6: Curved arrows and reaction mechanisms
Oct 2 Chapter 7: Nucleophilic substitution reactions
Oct 9 no recitation
Oct 16 no recitation
Oct 23 Chapter 8: Elimination reactions
Oct 30 Chapter 9: Additions reactions to alkenes
Nov 6 Chapter 10: Addition reactions to Alkynes
Nov 13 Chapters 11 & 12: Radical reactions and synthesis
Nov 20 Thanksgiving Holiday – no recitation
Nov 27 Chapters 12 & 13: Reactions, mechanisms & synthesis
Dec 4 Chapter 14: Reactions, mechanisms & synthesis

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