While every effort has been made to
make sure this electronic syllabus is error-free, it is not official.
The definitive source of course information remains the original (paper) syllabus distributed in class.
Click here for Chemistry 221 answer keys
Lycoming College Organic Chemistry II Spring 2004
Course Description This course is designed to introduce the student to the chemistry of alcohols, arenes, and carbonyl compounds. The approach will be both mechanistically and synthetically based. The spectroscopic tools used to discern organic structure will also be examined in some detail. The lab portion of the course will focus on synthetic organic chemistry, qualitative organic analysis, and mechanism. We will be building on some key concepts from Chem 220, such as, Lewis structures, formal charges, basics of polar rxn mechanisms, substitution/elimination pathways, and IR interpretation.
Faculty Dr. Chriss E. McDonald, (work phone 321-4186, home 433-4493, email firstname.lastname@example.org), no specific office hours but I'm usually around. If I'm not at school you can probably catch me at home. You may call me any time prior to 10 PM.
Lectures: MWF, 9:00-10:05, attendance will be taken daily.
Recitations: Problem solving sessions will be built into classtime. We will also have a weekly help session in the evening.
Assigned homework: These will not be graded. Homework will be discussed during the recitations. Obviously the homework assignments will be a crucial study element for quizzes and tests. Answer keys will be posted on the web.
Web-based supplements: These sites are useful for lab writeup info (physical properties): http://chemfinder.cambridgesoft.com/. Here’s a site which will be useful for our discussion of spectroscopy and structure determination: www.chem.ucla.edu/~webspectra/. The UCLA site allows you to click on the solution to the problem. Molecular data useful for lab reports can be found at: http://chemfinder.cambridgesoft.com/. Of course, the Mahler-derived department website is also quite useful in terms of links: www.lycoming.edu/chem/chemlink.htm Also, a chemical structure drawing program called Isis Draw can be downloaded for free: www.mdli.com
Exams: Exams 1-3 will be hour exams on the indicated days. The final exam will be an American Chemical Society standardized, multiple choice-type deal (cumulative over the whole of organic chemistry).
Labs: Similar to last semester. Prelab still in HBC 220. Note the times: T 7:45 -11:35 (220T), T 1:00 – 4:50 (220U), R 7:45 – 11:35 (220X). Be on time and come prepared!!!!!
Your grade will be based on the total number of points you obtain out of a possible 610.
Assignment of letter grades is based on the following scale: A 610 -549 (100 - 90%), B 548 – 488 (89 - 80%), C 487 - 427 (79 - 70%), D 426 - 366 (69 - 60%), F 365 - 0 (59 - 0%). The points will be distributed as follows:
quizzes 60 points
exams 1-3 300 points
final exam 100 points (cumulative ACS exam)*
laboratory 150 points
total 610 points
*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 mind your manners you will receive 3 points per speaker. 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 two bibliographic sources). The ceiling on bonus points is 12. (excluding those on exams).
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 at least one hour per day outside of class for starters. 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 we need to know the earlier material to comprehend the latter. Speaking of the cumulative nature of organic chemistry, here is a list of Chem 220 topics that significantly impact our studies in Chem 221. I strongly suggest these topics be reviewed prior to studying the relevant new material.
Lewis structures lab manual Appendix F all mechanistic discussions ubiquitous
Functional groups Chp 3 all synthetic discussions ubiquitous
curved arrow notation 5.4,5, Appendix F all mechanistic discussions ubiquitous
formal, partial charges 2.1, Appendix F all mechanistic discussions ubiquitous
E+ addition to alkenes 6.8-10 E+ aromatic substitution Chp. 16
SN2/SN1 Chp. 11 alcohols/ethers/carbonyls Chps. 17,18
infrared spectroscopy Chp. 12 NMR spectroscopy Chp. 13
Attendance at quizzes and exams is mandatory. Makeups will be administered only if I deem the reason for the 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.
CHEM 22104 CHRONODYNAMICS
Date Topic Text Q/E
1/12 introduction/radicals 5.2,3,8
1/14 representative radical chains 7.10, 10.3,4
1/16 mass spectrometry 12.1-3
1/19 NMR theory 13.1-3,8,9
Chp 27, lab manual
1/21 chemical shift and coupling 13.10,11,13 Quiz 1
1/23 proton NMR problems -
1/26 carbon NMR 13.4,5
1/28 physical/spectroscopic properties of alcohols 17.1,2,12 Quiz 2
1/30 substitution/elimination rxns of alcohols 17.3,7, 18.3
2/2 redox chemistry of alcohols 17.8
2/4 Exam 1 - Exam 1
2/6 ethers 18.1,4
2/9 epoxides 18.7,8
2/11 diene structure 1.6-9, 12, 14.2
2/13 electrophilic additions to dienes 14.3,4
2/16 the Diels-Alder rxn (finest in org. chem.) 14.5,6
2/18 intro to arenes 15.1-3 Quiz 3
2/20 Huckel's rule and arene spectroscopy 15.4-10
2/23 electrophilic aromatic substitution (EAS) 16.1-4
2/25 EAS on substituted arenes 16.5-6 Quiz 4
2/27 EAS on disubstituted arenes 16.7
3/3 Spring Break Week -
3/8 substituent modifications and multisteppers 16.10-12, 24.8
3/10 Exam 2 Exam 2
3/12 aldehyde/ketone (A/K) intro, synth of A/K 19.1,2, 16
3/15 addition of H:-. R:- to A/K 19.3,4,5,8, 17.5,6
3/17 addition of protic nucleophiles to A/K 19.6,7, 9, 11
3/19 as above as above last day to drop
3/22 A/K synthetic and mechanistic problems Chp. 19
3/24 the Wittig rxn 19.12 Quiz 5
3/26 carboxylic acids 20.1-3, 7,10
3/29 carboxylic acid derivatives 21.1,10
3/31 nucleophilic acyl substitution (NAS) 17.5,6, 21.2-7 Quiz 6
4/2 more NAS as above
4/5 addition of H:-. R:- to acid derivatives as above
4/7 Exam 3 - Exam 3
4/9 no class -
4/12 keto-enol isomerism 22.1
4/14 enol-based rxns 22.2-4
4/16 generation of enolates 22.5,6
4/19 alkylation of enolates (SN2) 22.7,8
4/21 addition of A/K to enolates 23.1-7
4/23 NAS of enolates 23.8-10
4/26 final exams
LAB SCHEDULE SPRING 2004
The lab component of this course is worth 150 points. Except for the three week Qualitative Organic Analysis lab, all of the lab writeups will be worth 15 points each. The QOA lab will be worth a whopping 30 points. Many of these experiments will be inquiry-based and will impact what we do in lecture as well. Students who do not conform to my notions of laboratory etiquette (as described in Chp. 1 of the lab manual) will be penalized. You will be expected to be on time, to read the experiment ahead of time, to perform the experiment in a safe manner, to keep your personal area and the common areas of the lab clean, and to be courteous to your labmates. The penalty for late lab reports is 5% per school day.
1 1/13,15 Radical Polymerization of Chp. 41A 1/20,22
Methyl Methacrylate, Check-in
3 1/27,29 as above (NMR, IR)
4 2/3,5 GC Analysis of an Isomeric Chp. 31, 19 2/10,12
Mixture Generated by EAS
5 2/10,12 The Acylation of Anisole Chp. 30 2/24,26
6 2/17,19 as above (IR, NMR)
7 2/24,26 The Diels-Alder Cycloaddition Chp. 29 3/9,11
8 3/9,11 Qualitative Organic Analysis Chp. 33 3/30,4/1
9 3/16,18 as above
10 3/23,25 as above
11 3/30,4/1 The Synthesis of N-Methyl Chp. 43 or part 1: 4/13,15
Prozac or The
12 4/6,8 as above part 2: 4/20,22
13 4/13,15 as above
14 4/20,22 as above, check-out ____
#A 15 point lab quiz will be on stoichiometry, sig figs, and IR spectral interpretation. It will be given during the week 2 reflux period.
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