Fall 2000 Organic Chemistry 1 Lycoming College

Course description - This course is designed to introduce the student to the chemistry of alkanes, alkenes, alkynes, and alkyl halides. The approach will be both mechanistically and synthetically oriented. The laboratory component of this course will involve the basic techniques of synthetic organic chemistry.

Faculty Responsibilities Office

Dr. Chriss McDonald* lectures, lab, recitations HBC 233

Holly Bendorf lab HBC 209

*321-4186 (work), 433-4493 (home, call up to 10 PM [no kidding]), or e-mail (mcdonald@lycoming.edu)

Texts etc.

a. Organic Chemistry,5^th ed by McMurry^#

b. Chemistry 220 Lab Manual, by McDonald,Bendorf, and Berkheimer^#

c. Bound laboratory notebook by Freeman^#

d. Lab safety glasses^#

e. Calculator (add, subtract, multiply, divide, logs)^#

f. Lab deposit, $10 at lab check-in, cash only (refundable upon checkout)

^#available at the bookstore

Course format

Lectures - MWF, 9:00 – 10:05, HBC G09, Attendance required.

Recitations – Problem solving sessions will be built into classtime. We will also have a weekly help seesion in the evening.

Assigned homework - Problems designed to enhance your understanding and prepare you for testing situations. A key will be posted on the web and outside my office. Homework will not be collected.

Web-based supplements-

a. Organic Chemistry Online CD in your text (problems and tutorials)

b. Homework keys, old tests, and exam study guides (web address to follow);

c. www.chemfinder.camsoft.com great for looking up physical property info for lab writeups;

d. Departmental homepage- many links to useful chemistry info;

e. Chemical drawing program for your computer! www.mdli.com/cgi/dynamic/welcome.html (click on download center then click on Isis/Draw.

Laboratory - T: 7:45 – 11:35 pm; Tuesday, U: 1:00 – 4:50 pm, Tuesday; X: 7:45 – 11:35 pm, Thursday, HBC 220, 234. Attendance required. Here you will experience what chemists actually do. Your labwork will be evaluated as described in the lab syllabus as well as on the lecture exams. Approximately 5% of each exam will be drawn from the labwork. A lab syllabus will be distributed at the first lab session. Make sure and show up with your $10 lab deposit (cash only) that first week. Meet at 9:30 for morning lab sections this first week.

Grading scheme

a. The final grade is based on the number of points obtained out of a possible 586 points. The points will be distributed as follows:

intro/biography 06 points (01%)

quizzes 70 points (12%)

exam 1 80 points (14%)

exam 2 100 points (17%)

exam 3 100 points (17%)

final exam (cumulative)* 120 points (21%)

laboratory 110 points (19%)

total 586 points (100%)

*a higher score on the final exam can be used to replace a lower score from exam 1-3.

As always you will have the opportunity to obtain bonus points through attendance at our colloquium series. Assuming you stay for the whole show and you mind your manners you will receive 3 points per colloquium. You may also receive up to 8 bonus points by writing a paper on a topic that we have mutually agreed upon (2-3 pages, typewritten, double spaced, with a minimum of 2 bibliographic sources. The ceiling on bonus points (excluding bio assignment and those on exams) is 15.

b. Assignment of letter grades is based on the following scale: 527 - 586 A, 469 - 526 B, 410- 468 C, 352 - 409 D, < 351 F.

c. A word about learning chemistry. Studying chemistry is hard work for most people (this is certainly true for me). I would recommend that you work on the lecture material one hour per day outside of class for starters (7 days per week). Once you see how things are going this amount can be adjusted as needed (I suggest a significant increase in study time prior to an exam). If you are having trouble make sure and come and see me. I’m easy to talk to and will do whatever I can to help you. You will be responsible for all of the material listed on the following schedule for the indicated exams and quizzes. It is not sufficient to learn the material from the lecture alone. You are expected to read and think about the material prior to the lecture. We must necessarily cover a large amount of material so our pace must be geared towards those who are ready to learn. The hour exams will be somewhat cumulative in the sense that you will need to know the earlier material to comprehend the latter.

Policy on attendance

Attendance at quizzes and exams is mandatory. Makeups will be administered only if I deem the reason for absence to be legitimate and I am made aware of the absence beforehand. Each documented, unexcused lecture absence beyond the first two will cost you one point from your total.

Lycoming College Organic Chemistry 1 Fall 2000

Schedule

“Organic Chemistry nowadays almost drives me mad. To me it appears like a primeval tropical forest full of the most remarkable things, a dreadful endless jungle into which one does not dare enter, for there seems no way out.”

Freidrich Wohler, 1835

(the slayer of the vital force theory)

date topic text quiz/exam

8/28 hello organic chemistry! Preface, 1 (p. 1-3)

8/30 ionic,covalent bonds,Lewis structures 1.1, 4,5

9/01 formal charge,functional groups 2.1-3,12,13, 3.1

9/4 introductory molecular orbital theory 1.2,3,6,7

9/6 orbital hybridization 1.8-11 QUIZ 1

9/8 as above 1.8-11

9/11 acid-base reactions 2.4-10

9/13 curved arrow formalism in acid-base rxns 2.11 QUIZ 2

9/15 classification of organic reactions 5.1-5

9/18 polar reaction examples 5.6

9/20 EXAM 1 (80 points) - EXAM 1

9/22 basic thermodynamics/kinetics 5.7-10

9/25 naming/drawing alkanes 3.2-4

9/27 alkane properties, cycloakanes 3.5-8

9/29 alkane conformational issues 4.1-3

10/2 ring strain, cycloalkane conformers 4.4-13

10/4 structure/nomenclature of alkenes 6.1,3-5,7 QUIZ 3

10/6 addition of HX to alkenes - 6.8-10

10/9 as above + cation rearrangements 6.11,12

10/11 addition of X₂, halohydrin formation 7.2-3 QUIZ 4

10/13 oxymercuration, hydroboration 7.4,5

10/16 other alkene rxns 7.7,8

10/18 EXAM 2 - EXAM 2

10/20 alkyne nomenclature/structure additions to alkynes 8.1,2

10/23 alkyne HX, X₂ additions 8.4

10/25 alkyne hydrations, reductions 8.5,6

10/27 long weekend (last day to withdraw) -

10/30 enantiomerism 9.1-3

11/1 optical activity 9.4,5 QUIZ 5

11/3 sequence rule 9.6,6.6

11/6 diastereomers 9.7-10

11/8 stereochemical analysis of selected rxns 9.15-17 QUIZ 6

11/10 infrared spectroscopy: theory 12.5,6

11/13 infrared spectroscopy: interpretation 12.7-9

11/15 kinetics/ stereochemistry of substitution 11.1-3 QUIZ 7

11/17 the S_N2 rxn 11.4,5

11/20 the S_N1 rxn 11.6-9

11/22 thanksgiving -

11/24 thanksgiving -

11/27 the E2 rxn 11.10-12

11/29 EXAM 3 (100 points) - EXAM 3

12/1 the E1 rxn, summary of substitution and elimination 11.14,15

12/4 alkylation of alkyne conjugate bases 8.8,9, 11.16

12/6 multistep syntheses, pheromones 8.10

12/8 as above 8.10

12/11-15 FINAL EXAM WEEK (120 points)

Tell me about yourself …………… Please include the following info for full credit –

1. Name and what you like to be called; Chriss McDonald, you may call me Chriss, Dr. McD, or Dr. McDonald.

2. Major (and note whether it is intended or actually declared); As an undergrad (late 70’s) I was actually a medical

technology major.

3. Minor (and note whether it is intended or actually declared); An unofficial one in history.

4. Fr., So., Jr., Sr.; Very senior.

5. 4 digit code for the posting of grades; N/A.

6. Tell me two interesting/funny things about yourself; I've just discovered Napster and am using it heavily (even though I feel like a low-grade criminal), I have glow in the dark dinosaurs on my pillowcase.

7. Tell me about your background in chemistry. I thought chemistry was merely OK until I got to organic, went bonkers over that. Went to grad school at Miami of Ohio in synthetic organic chemistry. Still learning lots of cool stuff about

organic chemistry. I’m interested primarily in the development of new synthetic methods. Specifically the

development of new strategies for carbon – carbon bond formation.

8. A recent photo of yourself (2 point bonus); see below

Tell me about yourself …………… Please include the following info for full credit –

1. Name and what you like to be called;

2. Major (and note whether it is intended or actually declared);

3. Minor (and note whether it is intended or actually declared);

4. Fr., So., Jr., Sr.;

5. 4 digit code for the posting of grades;.

6. Tell me two interesting/funny things about yourself;

7. Tell me about your background in chemistry.

8. A recent photo of yourself (2 point bonus);