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The definitive source of course information remains the original (paper) syllabus distributed in class.


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Lycoming College                   Organic Chemistry II                          Spring 1999



Course Description  This course is designed to introduce the student to the chemistry of arenes, alcohols, and carbonyl compounds.  The approach will be both mechanistically and synthetically based.  The spectroscopic tools used to discern organic structure will also be examined.  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 mcdonald@lycoming.edu), 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.

Course Format  
Lectures:  MWF, 9:00-10:05, attendance will be taken as often as I remember.

Recitations:  These will be held every two weeks on Wednesdays, the meeting period prior to each quiz/test.

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.  Homework keys will also be posted on the web

Web-based supplements:  These sites are useful for lab writeup info (physical properties):  www.sigma-aldrich.com, www.fishersci.com/catalogs .  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. Of course, the Mahler-derived department website is also quite useful in terms of links:   www.lycoming.edu/dept/chem/ Also, a chemical structure drawing program called Isis Draw 2.1.4 can be downloaded for free (!).  Go to the Yahoo website and search Isis Draw and you’ll be able to find it.

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, T 1:00 – 4:50,  R 7:45 – 11:35.  Be on time!!!!!

Grading
Your grade will be based on the total number of points you obtain out of a possible 600.
Assignment of letter grades is based on the following scale:  A 620 -558 (100 - 90%), B 557 – 496 (89 - 80%), C 495 - 434 (79 - 70%), D 433 - 372 (60 - 69%), F 371 - 0 (59 - 0%).  The points will be distributed as follows:
 

quizzes 

70 points

exams 1-3 

300 points

final exam

100 points (cumulative ACS exam)*

laboratory

150 points

total 

620 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 15.   (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.

Attendance policy
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 will cost you one point from your total.


                                                     CHEM 221 CHRONODYNAMICS

Date 

Topic

Text 

Q/E

1/11 

Introduction/radicals

18.1-4

1/13

representative radical chain rxns

18.5,6,8,9 

1/15

mass spectrometry

18.14-16

1/18 
 

NMR theory

5.8-11, 
 lab manual Chp. 27

1/20

recitation 

-

1/22

NMR practice

5.12-14 

QUIZ 1

1/25 

NMR “subtleties” 

Chp.10

1/27

physical/spectroscopic properties of alcohols

11.1-4 

1/29

substitution/elimination rxns of alcohols 

11.15,17, 12.9, 13.8c 

2/1 

redox chemistry and alcohols 

11.9, 11.18 

2/3 

recitation

-

2/5

 EXAM 1 

EXAM 1

2/8 

diene structure 

19.4-7

2/10 

electrophilic addition to dienes 

19. 8,9

2/12 

the Diels-Alder rxn (finest in organic chem) 

19.12 

2/15

introduction to arenes 

20.1-3

2/17

 recitation

-

2/19

QUIZ 2 (30 pointer), no lecture

 QUIZ 2

2/22 

Huckel’s rule and spectroscopy of arenes 

20.4-8 

2/24

electrophilic aromatic substitution (EAS) 

21.1-5

2/27 

more EAS

21.6-10

3/1

SPRI

3/3 

           NG BR

3/5 

                        EAK

3/8 

EAS of substituted benzenes 

21.11,12 

3/10

recitation 

 -

3/12 

Exam 2 

-

EXAM 2

3/15

aldehyde/ketone (A/K) intro, synth of A/K 

14.1-6

3/17 

addition of H:-, R:- to A/K 

11.7,8,10 

3/19

addition of protic Nu-H to A/K 

14.7-14 

3/22 

as above 

14.7-14

3/24

recitation 

 

3/26

the wittig rxn 

22.5-8 

QUIZ 3

3/29

physical/spectroscopic properties of acids and esters 

15.1-4 

3/31

synthesis and acidity of acids 

15.5,6,8-10

4/2

Good Friday, no class

4/5

 interconversion of acids and esters 

15.11,12,14

4/7

recitation

-

4/9

EXAM 3 

-

 EXAM 3 

4/12

structure/spectroscopy of other carbonyl deriv.

 16.1-4 

4/14

NAS of other carbonyl derivatives 

16.5-9

4/16

H:-, R:- addition to carboxylic acid derivatives 

 15.17, 16.12,13

4/19 

keto-enol isomerism 

17.1,2,4

4/21

aldol condensation 

17.5,6

4/23

Claisen condensation 

17.7 

4/26-30

final exam week

 

                                        ORGANIC CHEMISTRY
                                     LAB SCHEDULE SPRING 1999

 The lab component of this course is worth 150 points.  Except for the three week Qualitative Organic Analysis lab, all of the labs will be worth 13 points each.  The QOA lab will be worth a whopping 31 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 (not 3% as written in lab manual).

WEEK DATES             TOPIC                                                                                          ASSIGNED  WRITEUP DUE
                                                                                                                                            READINGS

1/12,14 

 Radical Polymerization of  Methyl Methacrylate, Check-in

Chp. 41

1/19,21


 

1/19,21

 The BF3-Catalyzed Coversion of trans-Stilbene Oxide into ?? 
15 point lab quiz# 

Chp. 28

2/2,4

1/26,28

as above (NMR, IR) 

 2/2,4

GC Analysis of an Isomeric Mixture Generated by EAS

Chp. 31, 19

2/9,11


 

2/9,11

 The Nitration of Methyl Benzoate or Bromination of Acetanilide

 Chp. 30 
handout

2/23,25

2/16,18

no lab 

7

2/23,25

The Diels-Alder Cycloaddition

Chp. 29

3/9,11

3/9,11

Qualitative Organic Analysis 

Chp. 33 

 3/30,4/1

3/16,18

 as above

10 

3/23,25

as above

11 
 

3/30, 4/1

Searching the Chemical  Literature

Chp. 32

4/6,8

12  or 
 
 

 4/6,8 

The Synthesis of Butylbarbituric Acid or 
Synthesis of an Ant Alarm Pheromone

Chp. 37 or 
Chp. 40

part 1: 4/20,22 

13 

4/13,15

as above

 

part 2:  final exam

14 

4/20,22

 as above

check-out

#lab quiz will be on stoichiometry, sig figs, and IR spectral interpretation.  It will be given in prelab.


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