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SYLLABUS
CHEM 224 Organic Chemistry B 2nd semester
Spring 2013 - LOYOLA UNIVERSITY CHICAGO (LUC)
Lecture: #1180 Section 001 Tues+Thur 10:00 a.m. 11:15 a.m. Flanner Auditorium 133
Discussion: #1181 Section 002 Tues 1:00 p.m. 2:00 p.m. Dumbach 120
#1182 Section 003 Thurs 1:00 p.m. 2:00 p.m. Dumbach 120
Sr. Lecturer: Dr. C. Szpunar
Office: Flanner Hall 200B Contact: in person (preferred), 773-508-3128, cszpuna@luc.edu
Emergency Message: Chemistry Dept. Office, 773-508-3100, fax: 773-508-3086
Student Office Hours: Mon + Fri: 11:45-1:30, Tu-W-Th: 8:30-9:30, or by prior appt
Required:
1. Organic Chemistry, Wade, 7th ed. (navy blue), Prentice Hall, 2009 (ISBN 9780321592316) *or* 6th ed. (black), Prentice Hall, 2003 (ISBN 0-13-147871-0) *or* 5th ed. (white)
2. Study Guide and Solutions Manual, Wade & Simek, 7th ed. (ISBN 9780321598714) *or* 6th ed. (ISBN0 13-147882-6) *or* 5th ed.
Suggested / Recommended Materials:
Molecular modeling kit, Darling, Prentice-Hall, Freeman (Maruzen), Proteus, or equivalent
Spiral or bound notebook for homework problems
***NO ACCESS CODE NEEDED, NOR DESIRED, NOR SUGGESTED, despite recent bookstore offering.
Optional Materials (found helpful by some students):
Organic Chemistry as a Second Language II, Klein, Wiley (ISBN 978-0-471-73808-4).
Barrons Orgo Cards: Organic Chemistry Review, Wang, Razani, Lee, Wu, and Berkowitz
(ISBN 0-7641-7503-3).
Grading (approx weight below) with grade guidelines: > 90% A; 75-90% B; 55-75% C; grading m a y b e c u r v e d
k& E X A M S 2 d a t e s a n n o u n c e d ( s u b j e c t t o c h a n g e , a l t h o u g h u n l i k e l y ) N O M A K E U P S 4 5 %
U N E X C U S E D A B S E N C E S m e r i t a z e r o s c o r e .
E X C U S E D A B S E N C E S a r e h a n d l e d o n a c a s e - b y - c a s e b a s i s ; g r a d e w e i g h t i n g m a y b e a d j u s t e d , d e p e n d i n g o n t h e c i rcumstance(s); however, an excused absence MUST BE CORROBORATED and DOCUMENTED, e.g., accompanied by a note from the doctor, dentist, hospital rep, or funeral director; by a court summons; or by a plane ticket stub. With documentation, religious observance, university representation, or personal emergency constitutes an Excused Absence.
k& Q U I Z Z E S T B D U N A N N O U N C E D ( d u r i n g l e c t u r e , d i s c u s s i o n p e r i o d , a s t a k e - h o m e ) 2 0 % k& F I N A L d a t e a n n o u n c e d ( s c h e d u l e d b y C A S ) , n o a l t . d a t e / t i m e , N O M A K E U P S 3 5 %
k& H o m e w o r k - a s s i g n e d p e r c h a p t e r ; f e e l f r e e t o w o r k a n y / a l l p r o b l e m s t o a p p l y a n d m a s t e r c o n c e p t s .
k&k&k&k& O p t i o n a l S h o r t R e p o r t ( a s d e t a i l e d b e l o w , o n e o p t i o n O N L Y ) * * * B O N U S ( m a x i m u m o f 3 - 5 % )
P l e a s e n o t e t h a t b e c a u s e t h i s c o u r s e , O r g a n i c C h e m i s t r y , i s c u m u l a t i v e , c o m p r e h e n s i v e , a n d i m p r o v e m e n t - b a s e d a n d b e c a u s e t h e f i n a l - e x a m g r a de is deemed a culminating measure of a students progress, any student meriting an F on the final exam will achieve a recorded course grade no higher than D, despite total points; a final-exam score of D will merit a course grade no higher than C, despite total points; and a final-exam score of C will merit a course grade no higher than B, despite students standing otherwise (i.e., despite total points.)
Course Objective: To guide, encourage, and foster the learning and understanding of Organic Chemistry nomenclature, structures, properties, reactions, mechanisms, and syntheses by the individual student, helping him/her to connect, extrapolate, integrate, and apply the many different aspects learned.
Student Outcomes: If successful, the student will learn how to
identify the various classes of organic compounds, their methods of preparation, and typical reactions.
name and draw specific organic compounds.
postulate a logical reaction mechanism for simple organic reactions.
discriminate amongst relative stabilities of reaction intermediates.
plan and write out multi-step syntheses using known functional group transformations and reagents.
prepare for basic purification/separation techniques of organic compounds required in the laboratory.
analyze and interpret data from various instruments used in separating and identifying organic compounds:
IR, NMR, and UV-vis spectrophotometers and mass spectrograph.
Lecture and Discussion Attendance and Attention: Important and required. Feel free to bring your books and modeling kit to class. Better yet, use them. Prepare for lecture by prior scanning of new material. Come prepared for discussion, ready to ask questions on assigned homework or yet unassimilated lecture material.
Cell Phones: Please be courteous and respectful of others. Silent mode during lecture and discussion. Not allowed in sight or within hearing during exams, subject to confiscation. NO phone conversations in lecture hall or in discussion class before class, during class, after class AT ANY TIME! NO texting before class, during class, after class AT ANY TIME! If you must talk or text, take it outside.
Academic Honesty: Essential, expected, and enforced. Dishonesty dictates consequences which may include: (1) notification of Chemistry Department Chair, students Department Chair, and CAS Dean, (2) documentation in the students official university record, and (3)dismissal from the university. Immediate consequences will include a ZERO on any item in question (quiz or exam). Please refer to the LUC Undergraduate Handbook on policies or the CAS website: HYPERLINK "http://ww.luc.edu/cas/pdfs/CAS_Academic_Integrity_Statement_December_07.pdf" http://ww.luc.edu/cas/pdfs/CAS_Academic_Integrity_Statement_December_07.pdf).
Study Strategies and Suggestions: One may approach the study of Organic Chemistry in a manner similar to tackling a new foreign language. Its study will provide a basis to understanding future material building constantly, incessantly, and relentlessly on the structural and mechanistic information presented previously. Over two semesters, the course will cover functional groups, aliphatic and aromatic compounds, bonding, nomenclature, stereochemistry, conformational analysis, reaction mechanisms, multi-step syntheses, and spectroscopy. Because the course is cumulative and builds heavily on prior material, the best plan is to study Organic Chemistry regularly, every day, similar to practicing the piano. Collaboration on homework problems is encouraged, especially in a timely fashion. Feel free to join or initiate a study group. Experience dictates that positive outcomes (for exam and course grades) are directly proportional to working and understanding the assigned problems on a regular basis, i.e., applying the concepts learned to non-generic compounds.
Typically, Organic Chemistry is not efficiently self-taught. Overnight cramming will probably not produce success. The student should quickly scan the chapter or segment to be covered BEFORE lecture to improve lecture comprehension. After lecture, careful detailed reading of the chapter or segment and focused working of the assigned problems are expected. If anticipating a passing grade of C, the minimal time per week devoted to Organic Chemistry is estimated at 4 hr for lecture/discussion, 4-10 hr for reading, and 4-10 hr for homework.
Suggested Homework Assignment (Wade 7th edition):
Chap 15: 1, 4-18, 22-27, 30, 33
Chap 16: 3-4, 7-8, 9 (a,b), 12-29, 31-32, 38-39, 45
Chap 17: 1-2, 4-27, 29-32, 34-35, 38, 40-52, 54
Chap 18: 1-4, 6-12, 16-31, 34-40, 43-44, 47-51
Chap 19: 1-21, 25-32, 34-42, 44, 47, 56, 58
Chap 20: 1-33, 35-40, 45, 47, 50
Chap 21: 1-39, 43-54, 62, 64-65
Chap 22: 1-47
Chap 23: 1-14, 16-17, 21-22, 24-26, 28-31, 32 (a), 33-36, 40, 41 (a,b), 52-55, 63
Chap 24: 1-3, 20, 32, 33
Chap 25: 1-5, 9-15, 30
Chap 26: 21-29
(Wade 6th edition):
Chap 15: 1, 4-18, 22-27, 30
Chap 16: 3-4, 7-8, 9 (a,b), 12-29, 32, 38-39, 45
Chap 17: 1-2, 4-22, 24-27, 30-32, 38, 40-52
Chap 18: 1-4, 6-12, 16-31, 34-40, 43-44, 47, 49, 51
Chap 19: 1-21, 25-32, 34-42, 44, 47, 56, 58
Chap 20: 1-33, 35-40, 45, 47, 50
Chap 21: 1-39, 43-48, 50-54, 66
Chap 22: 1-47, 59-65, 67-69
Chap 23: 1-14, 16-17, 21-22, 24-26, 28-31, 32 (a), 33-36, 40, 41 (a,b), 52-55, 63
Chap 24: 3-6, 20, 32, 33
Chap 25: 1, 4, 8-9, 11-15, 32
Chap 26: 21-29
Topics: to be covered this semester:
12/13. Spectroscopy: Methods of Structure Determination (Review)
Electromagnetic spectrum, molecular vibrations, infrared spectroscopy, characteristic IR absorptions, IR spectra interpretation, mass spectrometry (MS), terminology associated with MS, nuclear spin, magnetic shielding, NMR spectrometer, chemical shift, chemical nonequivalence, peak integration, spin-spin splitting, time dependence, interpreting NMR spectra, combined spectroscopy problems.
15. Dienes, Conjugated Systems, UV Spectroscopy
Molecular orbital theory, 1,3-butadienes, electrophilic addition (1,2 and 1,4), NBS, Diels Alder rxn.
16/17. Aromatic Compounds
Benzene, Kekule structure, resonance, annulenes, MO theory, aromaticity, Huckels Rule, heterocyclic aromatics, electrophilic aromatic substitution, directing effects on electrophilic aromatic substitution, Friedel-Crafts alkylation and acylation, nucleophilic aromatic substitution, side-chain reactions of benzene derivatives, reactions of phenols.
18. Aldehydes and Ketones
Structure of the carbonyl group; nomenclature, physical properties, and spectroscopic properties of aldehydes and ketones; syntheses of aldehydes and ketones; addition reactions; Wittig reaction; condensation reactions; acetals; oxidation and reduction.
19. Amines
Nomenclature, structure, physical properties, basicity, salts of amines, phase transfer catalysis, spectroscopic properties, reactions of amines, sulfonamides, Hofmann elimination, Cope Elimination, arenediazonium salts, synthesis of amines.
20. Carboxylic Acids
Structure and nomenclature, physical properties, acidity, salts of carboxylic acids, spectroscopy, synthesis of carboxylic acids, nucleophilic acyl substitution, Fischer esterification, synthesis and use of acid chlorides, diazomethane, condensations of carboxylic acids, reduction, alkylation of carboxylic acids.
21. Carboxylic Acid Derivatives
Structure and nomenclature, physical properties, and spectroscopic properties of carboxylic acid derivatives, nucleophilic acyl substitution, hydrolysis of acid derivatives, reduction of acid derivatives, organometallic reactions, thioesters, carbonic acid derivatives.
22. Enols and Enolates
Enols, enolates, alpha halogenation, alkylation of enolates, formation and alkylation enamines, aldol condensation, dehydration of aldol products, crossed aldol condensation, aldol cyclizations, Claisen condensation, Dieckmann condensation, crossed Clai s e n c o n d e n s a t i o n , - d i c a r b o n y l c o m p o u n d s , M a l o n i c e s t e r s y n t h e s i s , a c e t o a c e t i c e s t e r s y n t h e s i s , c o n j u g a t e a d d i t i o n , M i c h a e l r e a c t i o n , R o b i n s o n a n n u l a t i o n .
2 3 . C a r b o h y d r a t e s
C l a s s i f i c a t i o n o f c a r b o h y d r a t e s , m o n o s a c c h a r i d e s , e r t h y r o a n d t h r e o d i a s t e r e r o m ers, epimers, nomenclature, cyclic structures of monosaccharides, anomers, mutarotation, reactions of monosaccharides, oxidation and reduction of monosaccharides, non-reducing sugars, formation of glycosides, ether and ester formation, osazone formation, Ruff degradation, Kiliani-Fischer synthesis, Fischers proof of configuration, determination of ring size, periodic acid cleavage, disaccharides, polysaccharides.
24. Amino Acids and Peptides
S t r u c t u r e a n d s t e r e o c h e m i s t r y o f t h e - a m i n o a c i d s , s y n t h e s i s o f a m i n o a c i d s , r e s o l u t i o n , s t r u c t u r e a n d n o m e n c l a t u r e o f p e p t i d e s a n d p r o t e i n s , p e p t i d e s t r u c t u r e d e t e r m i n a t i o n , p e p t i d e s y n t h e s i s .
2 5 . L i p i d s
M i s c e l l a n e o u s c a t e g o r y , c l a s s i f i c a t i o n b y s o l u bility: waxes, triglycerides, soaps and detergents, phospholipids, steroids, prostaglandins, terpenes.
Optional BONUS Report
CHEM 224, Spring 2013, Dr. Szpunar ***BE SURE to include on the cover sheet OR top right of p1:
a) your name
b) the date
c) CHEM 224 Tues/Thur Sec 001
d) lecturers name
***
Option 1 (max of 3%):
Visit the International Museum of Surgical Science and write a 3 pp. report (of 12-pt type, 1-in margins, double-spaced, and stapled) highlighting at least 2 of its exhibits. Neatly, attach a pamphlet from the museum on one of its exhibits.
You may wish to check to see if the # 151 Sheridan Bus (or equivalent) is more efficient than the CTA el; the bus may drop you closer to the museum, located just south of North Avenue Beach near the Polish Consulate (red-and-white flag, Polish eagle) on inner Lake Shore Drive.
1524 N. Lake Shore Drive
Chicago, IL 60610 USA
312.642.6502, fax 312.642.9516, info@imss.org
HOURS: May - September: Tuesday through Sunday 10 am 4 pm
October - April: Tuesday through Saturday 10 am 4 pm
ADMISSION: Adults $6, Students & Seniors $3
(Be sure to check the website for updates on the time, current fee, and free day!)
_________________________________________________________________________________________
Option 2 (max 5%):
Choose a drug or health care product with organic functionalities featured in the following articles, or any similar publication:
Chemical & Engineering News (C&E News), June 20, 2005, whole issue Top Pharmaceuticals, from aspirin to Viagra and more, approx. 50 pharmaceuticals.
C&E News, Sept. 25, 2006, cover story Addiction smoking, drug, and alcohol abuse, pp. 21-44.
C&E News, Oct. 30, 2006, cover story Biotechs , pp. 14-20.
C&E News, Nov. 13, 2006, cover story RNA , pp. 16-23.
C&E News, Oct. 2, 2006, cover story Mass Spectrometry proteins , pp. 17-25.
C&E News, Oct. 23, 2006, cover story Bacterial Banter , pp. 17-26.
C&E News, Dec. 4, 2006, cover story Pharm Year in Review, pp. 17-28.
Write a 4-6 pp. report (of 12-pt type, 1-in margins, double-spaced, stapled, with at least 3 pertinent references or citations at the end of the report). Include the following:
Explain why the drug or health care product is of importance or interest to you.
Identify all the functional groups from an organic perspective.
Propose how you might verify the various functionalities spectroscopically, esp. via IR and NMR. Mention other methods, as applicable, i.e., via UV and MS.
Suggest hypothetically how you might change the molecule synthetically, at one functional site minimally, and state what you hope to achieve efficaciously by doing so.
*** due on or before Thursday, April 4, by 1 p.m. ***
N.B.: This optional Bonus Report, either option, is intended for enrichment; points therefrom are only considered as a grade component IF the
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Lecture Outline (tentative, subject to change, as announced in lecture)
Week Date Chapter Topic ***EVENT***
1 Jan 15 *12 + 13* Review IR, MS, NMR
Jan 17 15-1 Conjugated Systems, UV Spectroscopy
2 Jan 21 *** *Martin Luther King Holiday** no classes ***
Jan 22 15-2
Jan 24 15-3
3 Jan 29 16-1 Aromatic Compounds
31 16-2
4 Feb 5 17-1 Aromatic Compounds - Reactions
Feb 7 17-2
5 Feb 12 18-1 Ketones and Aldehydes
Feb 14 18-2
6 Feb 19 *** *** TUESDAY *** EXAM I (Chapters 15-18)
Feb 21 18-3
7 Feb 26 19-1 Amines
28 19-2
8 Mar 4-9 *** **** SPRING BREAK ***
9 Mar 12 19-3
Mar 14 20-1 Carboxylic Acids
10 Mar 19 20-2
Mar 21 *** ** THURSDAY * EXAM II (Chapters 18-20)
11 Mar 26 21-1 Carboxylic Acid Derivatives **** last day to withdraw ***
Mar 28 21-2
Mar28-Apr1 *** *** Holy Thursday p.m. through Easter Monday ***
12 Apr 2 21-3
4 22-1 Condensations and Alpha Substitutions of Carbonyl Compounds
*** Optional BONUS report due ***
13 Apr 9 22-2
Apr 11 22-3
14 Apr 16 23-1 Carbohydrates and Nucleic Acids
Apr 18 23-2
15 Apr 23 24 Amino Acids, Peptides, and Proteins
Apr 25 25/26 Lipids / Intro to Polymers / Q/A (as lecture schedule permits)
16 Apr 30 Tues * Cumulative FINAL EXAM, 1-3 pm, FH-133
CHEM 224 Tu+Thur a.m. November 2, 2012 - Dr. Szpunar - PAGE 1
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