CHEMISTRY 252N SPRING 2008
ORGANIC CHEMISTRY II
Lecture:
MWF 11:30-12:18, Evans Laboratory 1008
Instructor:
Professor T. V. (Babu) RajanBabu
Office: 3081 Evans Lab; e-mail: rajanbabu.1@osu.edu.
Group webpage: http://www.chemistry.ohio-state.edu/~rajanbabu/
Office hours:
Tue 1:30-2:30 PM; Fri 1:30-2:30 PM. You may also make an appointment (by email) if you need to see me any other times. I WILL NOT ENTERTAIN ANY CHEMISTRY QUESTIONS
BY E-MAIL.
Teaching assistant: Jordan Page, 3083 Evans Laboratory; Office hours: Monday / Wednesday 12:30
– 1:30 (Room TBA). At other times by appointment only.
Recitations
section no.
call no.
day
time
01
02
03
04
05
06
04937-4
04939-5
04941-0
04942-5
04931-1
04944-6
T
R
T
R
T
R
10:30
10:30
11:30
11:30
12:30
12:30
location
AM
AM
AM
AM
PM
PM
McPherson 1008
McPherson 1008
McPherson 1008
McPherson 1008
McPherson 1046
Celeste 0110
[AS COURTESY TO YOUR FELLOW STUDENTS AND YOUR INSTRUCTORS, PLEASE TURN OFF
YOUR CELL PHONE BEFORE THE CLASS]
Text and Study Aids: “Organic Chemistry”, 5th edition by Vollhardt and Shore (ISBN 0-7167-9949-9)
Student Solutions Manual for 5th edition by Shore (ISBN 0-7167-6172-6)
Molecular models set (ISBN 0-7167-4822-3)
Course packet available on Carmen
Prerequisites: Completion of Chemistry 251 or equivalent. I expect you to have a working knowledge
of the basics of bonding in organic and inorganic compounds, kinetics and thermodynamics of chemical
reactions, chemistry of alkanes, alcohols, and alkenes. You should also be able to identify common
organic functional groups. Take a look at the inside green flaps at the end of the book. They give you a
quick review of the essential materials. Review the following materials in your book before starting this
class: electronic structure, concept of bonding, molecular geometry, acid-base chemistry, concept of pKa,
basics of kinetics and thermodynamics, mechanism of radical reactions, electrophilic addition to alkenes,
SN1, SN2, E1 and E2 mechanisms. In general you will be assumed to have mastered chapters 1-9 and 12
of your text.
Withdrawal: The last date for withdrawal from this class without a W in your transcripts is April 17,
2009 and, with a W is May 15, 2009. The university will not generally allow withdrawal from the course
after this date even with petitioning. So plan ahead!
Course Objectives: Your objective for this course should be to develop an understanding of: (a) the
fundamentals of spectroscopy – nuclear magnetic resonance, infrared, ultraviolet, and visible – and how
these methods are used for identification of organic compounds; (b) chemistry of alkynes and dienes; (c)
structure and chemistry of aromatic compounds; (d) properties and reactions of carbonyl compounds
1
including carboxylic acids. I expect you to demonstrate that you have mastered the topics discussed
later in this syllabus by obtaining a satisfactory grade for the course. In addition to the synthesis and
interconversions of the classes of compounds mentioned, their utility for preparation of useful materials
such as pharmaceuticals, agrichemicals and polymers will be briefly mentioned (The CHEMICAL
HIGHLIGHTS sections in your book is a good place to look for these). A study of the mechanisms of
the organic transformations should help understand the basis of many organic, biochemical and industrial
processes. I hope that what you learn in this course will help you with other chemistry, biochemistry,
material science, and chemical engineering courses you will be taking later in your academic program.
As instructors, our objective is to help you learn the material through lectures, recitations and help
sessions, and the use of study aids. In addition we also have to develop fair and equitable testing
protocols to ascertain your mastery of the subject.
Web location: https://carmen.osu.edu/
This site will provide you with access to; (1) syllabus, (2) your grades, (3) practice examination and
answer keys, (4) ancillary materials to be announced in class or through e-mail. To view the web pages
you will need the Adobe Acrobat reader installed on your computer. If you do not have this, you can
download it for free from: http://www.adobe.com/products/acrobat/readstep.html
For Carmen, your user name is your surname.# (first part of your OSU email address). Your password
should be the same one that you use for your OSU email address.
For Assistance with Carmen: Go to http://telr.osu.edu/carmen/
Instructor’s Lecture Notes will be available on Carmen at the end of each two-week period (starting
week 2).
QUIZZES
There will be a total of 5 20-minute quizzes (given during the recitation starting with the second week
(week of March 6, for exact dates, see below). Each quiz is worth 20 points and the lowest quiz grade
will be dropped. NO MAKEUP QUIZZES ARE PLANNED. You have to take your quiz in your recitation. No
exceptions!
A week’s quiz will cover all material covered until the Thursday of the previous week.
During the recitation period on the dates indicated below:
Quiz 1:
Quiz 2
(MIDTERM I
Quiz 3
Quiz 4
(MIDTERM II
Quiz 5
April 7 or 9
April 21 or 23
Tuesday April 28, 6:30-8:30 PM, location to be announced)
May 5 or 7
May 19 or 21
Tuesday May 26, 6:30-8:30 PM, location to be announced)
June 2 or 4
EXAMINATIONS
There will be two midterms and a final. NO MAKE UP EXAMINATIONS ARE PLANNED. If there are
extenuating circumstances, such as a conflict with another course or a medical condition, sufficient
documentation must be provided. In the case of a medical excuse, you must have a note from a doctor
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that specifically states the following: (1) student named visited my office on specific date and time; (2)
student’s medical condition will prevent him / her from taking the exam scheduled for time / place. I
don’t need the details of your condition. However, the statement must be signed by the doctor and you
should provide the doctor’s contact information. Notes that simply state that you visited the doctor’s
office are NOT sufficient. I will not accept notes from ‘walk-in’ clinics such as minute clinics at popular
pharmacies. The instructor (not the TA) must be notified in writing (use e-mail) as early as possible,
before the examinations.
• Makeup examination must be scheduled within 2 days of the regular examination. I cannot guarantee
that you will be taking the same examination as everyone else especially if the examination is taken after
the currently scheduled time.
• Any planned absences should be brought to the attention of the instructor no later than the second
Friday (April 10) of the quarter and prior permission should be obtained for alternate examinations. No
requests after this date will be entertained, and no exceptions will be allowed.
Examinations will be given on the dates shown below, and will last approximately 2 hours. It may
consist of two parts. Part 1 maybe be multiple-choice or short-answer type questions, and in part 2, you
will be expected to provide more descriptive answers to questions like the ones from the suggested
homework problems at the end of each chapter.
You will be handed a numbered examination. At the end of the examination, you should return the
answer book to your TA and sign out on a roster that will be made available by the TA.
Molecular models will be allowed during examinations. Come prepared with some basic structures
(methyl groups, double bonds, cyclohexane, for example) already constructed to save time. No phones,
calculators, iPod’s, or scrap paper will be allowed. Use the back-pages of the examination for rough
work. Only answers placed in the indicated locations in the examination booklet will be graded.
Request for re-grading must be made in writing to your TA by 5:00 PM of the Wednesday of the week
following your examination. We will not honor such requests after that date. Clearly identify the
question that you want re-graded and give a one-sentence explanation of why your examination deserves
re-grading. As much as we try to avoid it, rare mistakes in grading do happen, and can result in more or
less points for you. So the entire examination will be re-graded.
EXAMINATION DATES (ALL TENTATIVE):
Midterm 1 [On material covered till April 24]
Midterm 2 [On material covered till May 22]
Final
[Comprehensive]
Tuesday, April 28, 6:30-8:30 PM (location TBA)
Tuesday, May 26, 6:30-8:30 PM (location TBA)
Thursday, June 11, 11:30 AM-1:30 PM (location TBA)
Keys will be will be posted on Carmen.
GRADING AND TOTAL POINTS
The distribution of points will be as follows:
4 Quizzes
Midterm I
Midterm II
Final (comprehensive)
Total
80 points (16%)
125 points (25%)
125 points (25%)
170 points (34%)
500 points
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For the ranges of total points shown below, the grades will be guaranteed. Depending upon the overall
performance of the class, minor adjustments maybe made at the end of the course.
Total points (percentage)
500-425 (100-85%)
424-375 (84-75%)
374-300 (74-60%)
299-250 (59-50%)
Below 250 (50%)
Grade
A
B
C
D
E
Plus and minus grades will be assigned based on how close you are to the border. For example, 427/500
maybe an A– while 420/500 may be a B+. or 380/500 may be a B–.
OTHER USEFUL INFORMATION
REVIEW SESSIONS: A review session will be held each Sunday before the examination week (NOTE
THE TIMES AND LOCATIONS): room will be announced in class and also posted on Carmen.
READING: You are responsible for all the topics in the chapter sections identified, including items which
I will not have time to cover in class. I expect you to keep your reading ahead of the lecture. I will not
have time to discuss the topics designated as prerequisite, or some portions covered in the reading
assignments, but you are responsible for ALL such assignments.
STUDY TECHNIQUES:
• Your performance in class will greatly improve by regular attendance and active participation in
recitations. YOUR TEXT BOOK HAS LOT MORE MATERIAL THAN WE WILL HAVE TIME TO COVER.
ATTENDING THE CLASS GIVES YOU A SENSE OF WHAT IS THE MOST IMPORTANT, IN CASE YOU
ARE OVERWHELMED BY WORK LOAD.
• You should prepare for each class by reading ahead.
• There is no such thing as a stupid question. The only stupid question is the one that you don’t care to
ask. I encourage you to participate in class discussions.
• Use the recitations, office hours, or the review sessions to clarify anything you have not understood
clearly during lectures.
• With such a large class, it is difficult to answer questions in class during lectures. However, I will try
my best to accommodate as many of these questions as possible in class.
• You are also welcome to stop by to clarify materials/ask questions before and after the class.
• I believe that most of you heard about Organic Chemistry being difficult is mostly part of an urban
legend. With consistent work, you will find it no more difficult than one of your General Chemistry
courses. That means you should spend roughly 2-3 hours per class reviewing the lecture, recopying
the class notes, attempting problems and reading the text.
• Review materials from Chemistry 121-123, 251 as needed.
• IT IS NOT ENOUGH TO READ THE TEXT ALONE. IT IS IMPORTANT THAT YOU PRACTICE
WRITING DOWN STRUCTURES, EQUATIONS, AND MECHANISMS, AND MOST
IMPORTANTALY, DO PROBLEMS. This is the best way to retain what you have gone over. There
are two types of problems in your text, ‘in chapter’ exercises, and the ‘end of chapter’ problems. Do
ALL the problems in the text as you come to them and as many questions as possible from the end
of the chapter. DO NOT LOOK AT THE ANSWERS IN THE STUDY GUIDE UNLESS YOU
ABSOLUTELY HAVE TO. USE THE TEXT TO SOLVE THE PROBLEM. EVEN IF YOU DO ONLY ONE OR
TWO PROBLEM PER HOUR, DOING IT BY USING THE TEXT / CLASS NOTES RATHER THAN THE
STUDY GUIDE WILL HELP IMMENSELY. Try these problems before you go to the recitation session.
Your TA will introduce you to the process of solving the problems and try to help you with any
4
questions. Familiarity with the suggested problems will make the examinations easier. Refer to the
study guide or seek help only after you have made an earnest effort. Finally, take advantage of the
office hours of the instructor and / or your TA.
•
In organic chemistry, a lot of structures and concepts involve visualization in 3
dimensions. You should make it a habit to make and visualize molecular models when
considering structural / stereochemical issues. THIS WILL TAKE SOME PRACTICE. BE
PATIENT. As I said before, come prepared with some basic structures (methyl groups, double
bonds, cyclohexane, for example) already constructed to save time in examinations. I will also
instruct you to bring some models to the class when this is appropriate.
Models will be allowed for examinations.
RECITATION: In addition to doing quizzes, recitations will be used to do some of the homework / model
problems suggested. The TA will walk you through the technique of solving the problems. He will also
answer any questions you may have regarding the lecture material. On a day when a quiz is scheduled,
it may take up to approximately 20 minutes at the end of the recitation.
SUGGESTED HOMEWORK PROBLEMS: You should work ALL the in-chapter problems, which appear
in the assigned reading. They provide a good check to see whether you fully understand the material
that precedes the questions. DO AS MANY OF THE END-OF-CHAPTER PROBLEMS AS YOU CAN (ALL IF
TIME PERMITS!). These are the types of questions you will encounter in the examinations and quizzes.
ACADEMIC MISCONDUCT
No form of cheating, however minor, will be tolerated. These include receiving or giving answers during
examinations and quizzes, altering grades or answers on graded examinations. We do photocopy
selected examinations before returning them to you. All suspected cases of misconduct will be handled
according to OSU procedures via the Committee on Academic Misconduct.
STUDENT WITH DISABILITIES
All students with documented disabilities, who need accommodations, should see the instructor privately
to schedule an appointment as early in the quarter as possible, preferably during the first week of
classes. If your disability requires materials in alternative format, please contact the Office for Disability
Services at 292-3307, Room 150 Pomerene Hall. The Office of Disability Services has a web home page
located at: http://www.ods.ohio-state.edu
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Important Dates (All examination dates are tentative)
March 30, Monday
First day of class
April 7 or 9
Quiz 1
April 17, Friday
Last day to drop/withdraw without W in your transcript
April 21 or 23
Quiz 2
April 26, 1:00 – 3:00 PM
REVIEW I, Evans 1008
April 28, Tuesday 6:30-8:30 PM
MIDTERM I, location to be announced
May 5 or 7
Quiz 3
May 15, Friday
Last day to drop with a W in your transcript
May 19 or 21
Quiz 4
May 24, Sunday, 1:00 – 3:00 PM
REVIEW II, location to be announced
May 25, Monday
Memorial day, no classes
May 26, Tuesday 6:30-8:30 PM
MIDTERM II, location to be announced
June 2 or 4
Quiz 5
June 5
Last day of classes
June 07, Sunday, 1:00 – 3:00 PM
REVIEW III, location to be announced
June 11, Thursday 11:30 AM-1:30 PM COMPREHENSIVE FINAL EXAMINATION (EA 1008)
6
Tentative Lecture Schedule and Reading Assignments
(Read the relevant sections before coming to the lecture)
Dates
Ch.
Topics
Suggested Problems
(chapter no. in bold)
Suggested Reading
March 30, April 1, 3
10
NMR
21-35
10.1-10.9 pp. 387-426; Highlights 10.1-10.3
10
NMR
36-48; 56-59
10.1-10.9 pp. 387-426; Highlights 10.1-10.3
April 13, 15, 17
11
Alkenes
April 20
11
Alkenes, MS, IR
11.26-11.29; 11.31-11.51;
April 22
11/12
Alkenes
April 24, 27
13
Alkynes
11.56-11.58; 11.64-11.68; 12.29-12.39; 12.
44, 45, 49-54; 56, 58, 59, 67-70
13.21-27; 30-44; 48; 50-54
April 6, 8, 10
(chapter no. in bold)
11.1-11.8
April 28 (Tue) 6:30-8:30 PM - Midterm I (on topics covered till April 24)
Delocalization, dienes,
14.28-50, 14. 52, 54, 57, 63, 64, 66, 68, 69. 71April 29, May 1, 4
14
UV
74.
Benzene
and
15.33-40; 42-47; 49-52; 56, 57, 60, 63-67
May 6, 8, 11
15
Aromaticity
11.9-11.11
READINGS from Chem 251: 12.1-12.6, (pp. 510-516) 12.8 (pp.
520-522), 12.10-13 (pp 520-533)
13.1, 13.2, 13.3 Spectroscopy (Read NMR and IR- WILL NOT BE
COVERED IN THE CLASS); 13.4; 13.5 13.6, 13. 7/13.8 13.9,
FYI: 13.10 and Highlights 13-1
14.1-14.5 pp. 602-613; p.622; 14.6-14.8 pp. 614-632; 14.11
pp. 642-647. FYI: 14. 10; Highlight 14.2-4.
15.1-15.3; 15.4 Spectroscopy (read, will not cover in class);
15.5-15.7 pp. 679-692; 15.8-15.13 pp. 692-708
Highlight 15.1
May 13, 15, 18,
16
Electrophilic Aromatic
Substitution
16. 28-41; 43, 44, 46, 47, 48, 49, 52, 53,
57
16.1-16.6
FYI 16.7; Highlight 16.1 (TNT and Picric Acid)
May 20, 22
17
Aldehydes and Ketones
17.20-23; 17. 25-35; 17. 37-38, 17. 40-53; 17.
56-60
17.1- 17.3, 17.4 [also 8.6 Chromium (VI)-oxidations), 12.12
(Ozonolysis). 15.13 (Friedel-Crafts Acylation]
17.5 also 8.6-8.8 (Hydride and organometallic additions)
17.6-17.8; Highlight 8.2 (p. 301: The breath analyzer test)
May 25 Memorial Day, No classes
May 26 (TUE) 6:30-8:30 PM - Midterm II (on topics covered till May 22)
Aldehydes and Ketones
May 27, 29
17
June 1, 3, 5
19
Carboxylic Acids
19.23-31; 19.32 (a)-(g); 19.33; 19-36-38;
19.41-43; 19.48-53
June 11 (Thu) 11:30 AM-1:30 PM - Comprehensive Final Examination
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17.9-17.14; Highlight 17.1, Imines in Biological Transformations
(p. 786); 17.2 Wittig Reaction sin Synthesis (p. 794)
19.1-11 (pp. 856-882; FYI: 19.13
HIGHLIGHTS 19.2-19.4
CHEM 252N
T. V. RajanBabu
Types of Questions on Quizzes and Examinations
1. Arrange in order of a chemical or physical property.
EXAMPLE: Arrange in order of heat of hydrogenation per double bond (–ΔH in kcal/mole/number of
double bonds) in the total hydrogenation of the following compounds.
a
b
c
d
2. Provide explanation for a chemical or physical property, or explain the reactivity of a
chemical.
EXAMPLE: Explain why ammonia, NH3 is pyramidal not trigonal.
3. Given starting materials, reagents and reaction conditions, predict the major products.
EXAMPLE:
OMe
H2SO 4 (catalytic)
+
Products?
EXAMPLE:
CH3
Br2, initiator, heat
product(s)
4. Given starting materials and products provide the reagents and approximate reaction and
workup conditions needed to carry out the transformation.
EXAMPLE:
H
Me
Br
Me
Reagents and
reaction conditions
H
[more than one step maybe needed]
SCH3
Me
Me
Reagents and
reaction conditions
[more than one step maybe needed]
5. Given a product, propose a synthesis from readily available starting materials and
reagents.
Reagents and
reaction conditions
starting
mateial
[more than one step maybe needed]
HO
6. Show a synthetic application of a reagent in a ‘real’ example (should be non-trivial, and
should illustrate some unique property of the reagent, no R substituent, or generic
structures).
EXAMPLES
BH3, OsO4, p-TosCl, N-Bromosuccinimide, m-CPBA, pyridinium chlorochromate
EXAMPLES
H3PO2, Diisobutylaluminum hydride, Me2CuLi, CuCN, 18-crown-6, NaB(CN)H3
7. Provide clear, succinct definition of a concept, postulate, stereochemical term etc., with
examples.
EXAMPLE: • Define Hammond postulate and illustrate its use in explaining the orientation in the
electrophilic aromatic substitution (e. g., bromination) of nitrobenzene.
• Define stereospecificity and give examples to illustrate the principles involved.
• Define Hammond postulate and illustrate its use in explaining the reactivity of primary vs allylic bromde
in SN1 reactions.
• Assign the appropriate designations (R, S, Z, E, cis-, trans- etc.) for the relevant molecular unit.
H
Me
Br
CH3
Ph
CH3
CH3
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