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 homework and exam keys and other class materials





Dr. Holly D. Bendorf (lecture, lab)   Office: 209 HBC                  Phone: x4365 (office), 998-8647 (home)

Dr. Chriss E. McDonald (labs)          Office: 233 HBC                  Phone: x4186


Course Schedule:

            Lecture:           MWF  9:00 - 10:05

            Labs:                T  7:45 - 11:35 am,  T 1:00 - 4:50, and TH  7:45 - 11:35 am.


Office Hours:  M and W 10:15 – 11:15, TH 1:30 – 2:30 or just drop by.


Evening Review Session:  Time and location TBA.


Course Description:  CHEM 221, Organic Chemistry II, is a continuation of CHEM 220.  CHEM 221 will focus on the reactions of organic compounds and their mechanisms, the application of these reactions to organic synthesis, and the identification of organic compounds using modern spectrometric techniques.


Text and Materials:

• "Organic Chemistry," 6th ed., by John McMurry.

• Bound laboratory notebook (you can use your notebook from CHEM 220).

• CHEM 220-221 lab manual.

• Safety glasses or goggles (available at College Store).

• Calculator with logarithmic and exponential functions.


Other Useful Materials:  Copies of several organic chemistry texts (some with solutions manuals) are available in the reading room.  If you are not satisfied with McMurry's treatment of a topic in his text, feel free to consult one of the other textbooks--you may just find one you like.  Also, these texts are excellent sources of extra practice problems.  A useful web site for NMR practice can be found at www.chem.ucla.edu/~webspectra/


Grading Criteria:                   Quizzes (6)                                90 points          

                                                Exams (3)                                300 points       

                                                Laboratory                               110 points       

                                                Final                                        100 points       

                                                                                                600 points


Final letter grades will be assigned as follows:  540-600 A, 480-540 B, 420-480 C, 360-420 D.  Be aware that you must pass both the lecture and the laboratory to receive a passing grade for the course.     


Exams:  There will be three in-class exams on the following dates:  Friday, February 10; Friday, March 17; and Wednesday, April 12.  Exam questions will be based on the lecture notes, assigned reading and problems from the text.  The final exam is the American Chemical Society (ACS) standardized exam for organic chemistry and covers both semesters of organic chemistry.  It will be administered on the day and time assigned by the registrar.   


Quizzes:  Quizzes are an incentive to stay current with the course.  They provide you with a means of evaluating your progress and allow you to identify any potential "trouble spots" before you get into an exam.  The lowest quiz grade will be dropped.


Assignments from the Text:  The course outline lists the reading assignments for each class.  I highly recommend taking notes on the reading.  Chapter outlines with homework assignments will be distributed throughout the semester.  Although they will not be collected, it is strongly suggested that you complete the assignments and have any questions answered before the next class period.  We cover a lot of material in this course and those not prepared for class will have trouble keeping up with the pace.  Lectures and in-class assignments are prepared with the assumption that you have read the relevant sections in the chapter before class.  Some quiz and exam problems may be taken directly from the homework – this is intended as an incentive for you to work the text problems.  Answer keys for homework problems will be posted on the Chemistry Department web site (go to http://www.lycoming.edu/chem/ then follow the “schedules and syllabi” link to CHEM 221).


Review Session:  The evening review session is an informal workshop where you will have the opportunity to ask questions, review the course material, and work problems either individually or in groups.


Extra Credit:  Extra credit points (3) can be earned by attending departmental colloquia (provided you arrive on time and stay for the entire talk, including the question and answer period).  Extra credit points can also be earned by writing a brief research paper on a mutually agreed upon topic (up to 8 points, see me for more details).  Extra credit from colloquia and research papers is limited to 15 points, with a maximum “bump” of ½ of a grade (i.e., if you have earned a B+, extra credit can increase your grade to an A-, but not to an A).



- Regular attendance at lecture is expected.  Students with a perfect attendance record will receive a 5 point bonus.  Students who miss more than three classes (regardless of the reason) will receive a 5 point deduction from their final course grade.  Attendance at quizzes, exams and laboratory meetings is mandatory.   

- Missed quizzes cannot be made-up and will receive a grade of zero.  Remember, your lowest quiz grade will be dropped.  

- Missed exams will receive a grade of zero.  However, in exceptional circumstances such as medical or family emergencies, the grade on the final exam may be substituted for the missed exam.  For this to occur, the absence must receive prior approval from me and must be documented (i.e.; a letter from the Dean’s office).  A doctor’s appointment is not considered an emergency.    

- Missed labs will receive a grade of zero.  Lab make-ups will be permitted in some cases when the absence receives prior approval.  You must be able to attend another lab section in order to make-up a missed lab. 


Cell Phones:  Cell phones are not permitted in the lab or in lecture.  Please turn off your phone and keep it in your back pack or purse.  If your cell phone interrupts class or lab, you will be asked to leave.


Study Suggestions:  The material covered in CHEM 221 builds upon the concepts covered in CHEM 220.  Lectures, in-class assignments, and labs have been prepared with the assumption that everyone has a solid understanding of the material from CHEM 220.  You are therefore responsible for the CHEM 220 material and should review when necessary.  If you have any questions or would like some assistance in reviewing, please ask!


As you already know from CHEM 220, organic chemistry does not lend itself to memorization or last-minute cramming.  This is true to an even greater extent in CHEM 221 – the material is more challenging and we move at a faster pace.  You should plan on spending at least an hour/day on this course.  Start studying for exams approximately five days in advance…even if it means just spending some extra time reviewing the older material each day.  The best approach for studying organic is to practice everyday:  review your notes, study the text, discuss the material with your friends, quiz yourself, and most importantly, work lots of problems


Remember, my job is to help you learn organic chemistry – if you have questions or need extra help, please come and see me as soon as possible. 


Course Outline:


Although we may occasionally be a day ahead or behind the lecture schedule, the quiz and exam dates will not change.




Class Preparation




Read the following sections in the text:


Week 1




Jan. 9

Radicals, Rad. Halogenation

Chapter 5.2-3


Jan. 11

Rad. Hal.; Rad. Add'n to alkenes



Jan. 13

Polymerization, mass spectrometry

7.10; 12.1-4






Week 2




Jan. 16




Jan. 18

1H NMR - chemical shift



Jan. 20

1H NMR - spin-spin splitting


Quiz 1





Week 3




Jan. 23




Jan. 25

NMR wrap-up and problems



Jan. 27

Resonance Review


Quiz 2





Week 4




Jan. 30

Diene structure and properties

14.1-2, 10-13


Feb. 1

Reactions of dienes with electrophiles

14.3-4, 7


Feb. 3

Diels-Alder reaction


Quiz 3





Week 5




Feb. 6

Benzene: properties and structure



Feb. 8




Feb. 10



Exam 1





Week 6




Feb. 13

Electrophilic Aromatic Substitution



Feb. 15

More EAS



Feb. 17

EAS of subst. benzenes







Week 7




Feb. 20

Oxid'n and red'n of aromatic compounds



Feb. 22

Multistep synthesis of benzene cmpds

16.12 and pp 578 - 586


Feb. 24

Alcohols: prop., struct., acid-base chem.

17.1-3, 12

Quiz 4





Feb. 27




Mar. 1




Mar. 3

            No Classes








Week 8




Mar. 6

Reactions of ROH

10.7; 17.4, 7-9


Mar. 8




Mar. 10



Quiz 5





Week 9




Mar. 13

Aldehydes & Ketones: properties

pp 672 - 681 and 19.1-3, 16


Mar. 15

Prep'n of ald. and ket., Reactions

19.4-7, 17.5


Mar. 17



Exam 2





Week 10




Mar. 20

Reactions of A/K with nucleophiles

19.8, 17.6, 10.8-9


Mar. 22

Reactions of A/K with nucleophiles

19.6, 9, 11


Mar. 24

More reactions of ald. and ket.







Week 11




Mar. 27

Acids and Esters: struct and props.

20.1-5, 9


Mar. 29

Prep'n of acids and esters


Quiz 6

Mar. 31

Rxns. of acids and esters

20.8, 21.6






Week 12




Apr. 3

Acid derivs: structure and reactivity



Apr. 5

Interconversion of acid derivs-NAS


Quiz 7

Apr. 7

Nucleophilic Acyl Substitution







Week 13




Apr. 10

More Nucleophilic Acyl Substitution



Apr. 12

Exam 3


Exam 3

Apr. 14

No Classes - Good Friday







Week 14




Apr. 17

Keto-Enol Tautomerization



Apr. 19

Enolate chemistry



Apr. 21

Aldol, Claisen chemistry

23.1-4, 6-8




Laboratory:  It is imperative that you come to the lab fully prepared.  Careful planning and preparation before you arrive at the lab will allow you to complete your experiments in an efficient and safe manner.  It is your responsibility to read and understand the lab procedure before you arrive at prelab.  Missing or arriving late to prelab will result in a reduced lab grade (up to 5 points per violation) or dismissal from the lab.


The laboratory grade is worth a total of 110 points and consists of eight lab reports and two 10-point lab quizzes.  Late reports will be penalized 5% per school day.  Late lab reports will not be accepted after graded labs are returned in any section.    


Lab Safety:  Unsafe behavior in the lab will not be tolerated and violations will be penalized.  Repeated violations during a class may result in a zero for that lab.  Keep in mind that lab safety includes laboratory hygiene.  In the event that common areas are left dirty, (rotovaps, balances, melting point apparati, reagent hood) points may be deducted from the entire lab section.  If you have any questions regarding lab safety, please do not hesitate to ask. 


Lab Syllabus





Required Reading

Week Due

Point Value








Jan. 10, 12

Check-In, Rad. Polym.

Chap. 41A




Jan. 17, 19

Reaction of 1-octyne, lab quiz 1*

Chap. 6, 16, handout




Jan. 24, 26

as above (NMR, IR, GC-MS)

Chap. 24, 27




Jan. 31, Feb. 2

Diels-Alder Cycloaddition

Chap. 29




Feb. 7, 9


Chap. 31, 19




Feb. 14, 16

Acylation of Anisole

Chap. 45




Feb. 21, 23

as above (NMR, IR)

Chap. 24, 27




Feb. 28, Mar. 2

Spring Break





Mar. 7, 9

Q.O.A. (IR, NMR)

Chap. 33




Mar. 14, 16

Q.O.A. (IR, NMR)





Mar. 21, 23






Mar. 28, 30

Synthesis Project

Chap 34, 36, 43

part 1: 13



Apr. 4, 6

as above


part 2: last



Apr. 11, 13

as above


day of class


Apr. 18, 20

as above, lab quiz 2, check out











*Lab quiz 1 will cover significant figures, mole calculations, stoichiometry, and IR.



*Lab quiz 2 will cover stoichiometry, mole calculations, stoichiometry, IR and NMR.


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