You are on page 1of 43

Chem 140B

Chem 140B
Required Text: Organic Chemistry Structure and Function, 4th Edition, by K. Peter C. Vollhardt and Neil E. Schore, W. H. Freeman and Company, 2002. Suggested Text: Study Guide and Solution Manual for Organic Chemistry Structure and Function, 4th Edition, by Neil E. Schore, W. H. Freeman and Company, 2002 Pushing Electrons a Guide for Students of Organic Chemistry, 3rd Edition, by Daniel P. Weeks. Saunders College Publishing, 1998.
Course Home

Several other organic texts are available in the Science and Engineering Library. Use them when you desire additional reading or problems. You are strongly advised to stay ahead of the lectures in Calendar your reading!
TA Assignments Molecular Models: A personal set of molecular models is highly recommended. Models are

Syllabus

particularly important for the understanding of stereochemical relationships and 3-dimensional Exams structures. Various types are available. Models are not to be used on exams.
Suggested Reading

Teaching Assistants: Excellent teaching assistants will be working with me on this course. Check the course web page for current information about office hours. You may show up at any time during the specified hours, however, making an appointment is strongly recommended.

Quizzes: 3 quizzes will be given at the beginning of discussion sections (20 minutes, weeks 2,6,10). The quizzes will account for 15% of your total grade (60 points). The scores of different discussion sections will be normalized to remove differences in grading. No make-up quizzes !

Examination and Grading: There will be two 70-point midterm examinations and a 200-point comprehensive final examination. Be prepared to show a picture ID at all exams. Exams will be given only at the scheduled times. Make-up exams are not a possibility. The total points for this course are as follows:

Quizzes Midterms

60 points 140 points

(3 x 20) (two midterms, 70 points each)

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Syllabus.html (1 of 5)9/4/2007 7:19:08 AM

Chem 140B

Final

200 points Total 400 points

The following scale represents the guaranteed grade based on your performance. However, the results will be curved in the end of the quarter and lower percentage may give you higher letter grade.

Carefully check the grading on your examination after it is returned to you. Make no new marks on the exam! If there is an error, return the exam to me with a note indicating the error. If you feel a question has been improperly graded, return the test to me and I will regrade the entire exam. You may use either pencil or pen for the examinations. However, examinations taken in pencil will not be eligible for regrades. Be aware that when you request a regrade of an exam, the entire exam will be regraded and your score for that exam may go up or down! Exam scores will be considered final three days after the exams are returned to the class.

Academic Honesty: Please be aware of the UCSD policy on Integrity of Scholarship. Copying, discussing material or using reference material during an examination is cheating. Any student found cheating on an examination will receive a "0" on that examination and a letter explaining the reasons for this grade will be sent to the appropriate University officials for additional disciplinary action. Taking an examination for someone else or having someone else take an examination for you is a very serious offense for which expulsion from the University will be urged. Changing an answer on an exam that has been returned to you and then requesting a regrade is also a very serious offense. Remember that you may not drop or withdraw from a course while a dishonesty case is pending, or if found guilty.

Advice: Please stay caught up with the material. This is a lecture and text-based course. The text is most important for problems and for clarification of points from lecture. Lecture will often clarify and expand upon material covered in the text. To test your understanding, do as many of the suggested problems as possible. Check your answers in the Study Guide. If you don't understand a problem, first review the text and lecture notes, then see a TA or me. See additional hints below.

General Advice and Comments

Chemistry 140B is the second quarter of a three-quarter survey of organic chemistry. In this quarter we will study methods for identifying molecular structure as well as more reactions. This will set the foundations for planning a complex synthesis. Organic chemistry is a part of our everyday life and it

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Syllabus.html (2 of 5)9/4/2007 7:19:08 AM

Chem 140B

contributes to make our life easier, healthier and happy. Understanding the fundamentals of organic chemistry is crucial to revealing the secrets of biological systems.

How to do well in the course? Organic Chemistry is a rational subject and can be rigorously understood. Although it may have worked for you in other classes, memorization is NOT the right way to study organic chemistry. Certain facts have to be learned and recognized, of course, but understanding fundamental principles, general mechanisms and reactivity patterns is a much more effective approach to studying organic chemistry.

Although inherently not more difficult than other physical sciences, organic chemistry may appear different as a large amount of new conceptual material needs to be assimilated. Organic chemistry classes are highly cumulative and ideas introduced early on will be used to develop other concepts later. Thus, letting things slide is unwise, as the material begins to accumulate relentlessly. Waiting until a few days before an exam to begin learning the material is therefore a serious mistake. Continuous learning and constant practicing is a key for success. Do not fall behind.

Write, write, write. I cannot overemphasize the importance of writing in this course. Simply listening to lecture and reading your text is not enough. Sometimes it is very easy to convince yourself that you understand the material. Yet, solving problems is the best way to exercise and secure new concepts. Challenge yourself and enjoy putting the puzzles together. Try studying with a partner or in groups. You will be astonished at the insight that you gain when you hear another opinion or when you have to explain something to others.

Seeking help and advice from the instructors can make a huge difference. It seems too few students take advantage of this opportunity. Do not hesitate to come regularly to office hours. This time is set aside for this purpose! When you encounter a problem, however, first attempt to solve it yourself. If it persists, talk to your TA or me.

I wish that this journey will be scientifically stimulating and enjoyable for you.

Haim Weizman

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Syllabus.html (3 of 5)9/4/2007 7:19:08 AM

Chem 140B

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Syllabus.html (4 of 5)9/4/2007 7:19:08 AM

Chem 140B

Course Home | Syllabus | Calendar| Assignments| Exams| Suggested Reading

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Syllabus.html (5 of 5)9/4/2007 7:19:08 AM

1. The following figure represents a theoretical 1H NMR spectrum were all the peaks appear as singlets. a. (8 pt.) assign to each peak (on the line provided) a letter corresponding to the protons and the expected multiplicity (for example: proton g, (t). b. (2 pt.) what is the expected relative ratio of the individual lines of the peak at 3.19? (for example t, 1:2:1) ___________________

a b

PPM

2. (6 pt.) The following compound was dissolved in dry solvent and the NMR spectra were recorded.
OH HO

a.

a. How many signals will appear in the 1H NMR spectrum? ______________ b. How many signals will appear in the 13C (decoupled) NMR spectrum? ____________ c. What is the estimated chemical shift for the protons labeled with (a.)? Circle one: 0.5-1.5 1.5-2.5 2.5-3.5 3.5-4.5 5.5-6.5

3. (6 pt.) You were asked to evaluate a computer program that is capable of predicting chemical shifts based on structure. Using your 140B knowledge, you decided to use the following molecule for the test. These are the predicted chemical shifts:
h. 1.11 f. 5.60 e 5.60 d. 2.24 i. 1.11

g. 2.25 a 1.47 b. 1.71 c. 1.06

a. Which protons were miscalculated? ____________ b. Are you predicting that the experimental chemical shift will be in higher or lower field?_______________________ c. Why? Draw scheme.

4. Compound A is treated with a strong base. a. (6 pt.) using the following Newman projection template, draw the conformation that will lead to the most stable elimination product.

3S

Br 2S A front carbon is C2

b. (4 pt.) draw the structure of the product in the box. Is this E or Z isomer? Show how you determined the E/Z configuration.

Isomer

5. (10 pt.) Provide a detailed mechanism for the following reaction using a curved arrow notation.
O OH H2SO4

6. (10 pt.) Unknown compound has the molecular formula of C6H11O2Cl. The NMR spectrum of the compound in chloroform is presented below. The IR spectrum show strong peak at 1735 cm-1. What is the structure of the molecule? Draw your final solution in the space provided.

2H

2H

1H

6H

PPM

This space is for your work:

Final structure

7. (10 pt.) What will be the major product of the following reactions? Pay careful attention to the stereochemistry of the product.

Cl2

HCl

HBr H2O

H2

HBr radicals

Chem. 140B Fall 2004 1st midterm Last Name:____________ First Name_____________ Student ID:_______________ If you would like to have your test available for open pick-up, please sign below. (Note: Other students might see your grade if you choose this option). Signature:_________________________ This exam accounts for 70 points of your total 400. You have 50 minutes to complete the exam. Read carefully each question before answering. Look through the exam so you can best judge your time! You can use the back of the pages for rough draft, but your final answer should be written clearly in the spaces given. Exams written in pencil will not be regraded! Remember: Team work is not allowed and can lead to severe consequences!

Good luck.

Q 1 Q 2 Q 3 Q 4 Q 5 Q 6

Total

1.

The following figure represents a theoretical 1H NMR spectrum were all the peaks appear as singlets.

a. ( 8 pt.) assign to each peak (on the line provided) a letter corresponding to the identity of the protons and the expected multiplicity (for example: proton g, (t). b. ( 2 pt.) circle the carbon that will appear in the 13C NMR spectrum at 200.6 ppm.
b c f
O

a,e,f (s)

a e d (t)

H d b (t) c (q)

10

PPM

2. (6 pt.) The following compound was dissolved in CDCl3 and the NMR spectra were recorded.
O

a.

a. How many signals will appear in the 1H NMR spectrum? ______3________ b. How many signals will appear in the 13C (decoupled) NMR spectrum? _____3_______ c. What is the estimated chemical shift for the protons labeled with (a.)? Circle one: 0-1 1-2 2-3 3-4 4-5 5-6

3. ( 16 pt.) a. ( 3 pt.) Draw the structure of the most stable intermediate that is formed by protonation of 3-methyl-2-pentene.

b. ( 5 pt.) Draw the most thermodynamically stable isomer with the formula C7H12

c. ( 3 pt.) Draw a conformation that will lead to the following elimination product.

Br H3C H3C H
c. ( 5 pt.) Draw the rearrangement product of the following carbocation.

H Ph

CH3ONa (-HBr)

H3C H3C H

or CHCH3 C

4. (11 pt.) Provide a detailed mechanism for the following reaction using a curved arrow notation.

HBr

Br

CH3 H3C Br

+ Br

2O carbocation

Br

Br

3O carbocation

5. (12 pt.) Unknown compound was found to have a molecular formula of C7H11NO2. The NMR spectra of the compound in chloroform are presented below. The IR spectrum show strong peaks at 2227 cm-1 and 1740 cm-1. What is the structure of the molecule? Draw your final solution in the space provided.
1

H NMR
1.35 4.31 1.35

6H
2.80 2.62

1H

2H 2H

PPM

13

C NMR

180

160

140

120

100 PPM

80

60

40

20

Use this space for your work.

Final structure

6. (15 pt.) What will be the product(s) of the following reactions? Pay careful attention to the stereochemistry of the product.

Br Br2 CCl4 Br

OH H2SO4,

partial credit, take point if the double bond is not planar

Cl2 + enantiomer Cl

Cl

H2 Pd/C H + enantiomer H

Br2 MeOH MeO or Br another isomer

Practice Exam Solving this exam should take 1 hour max. Good luck ! 1. What will be the major product of the following reactions? Pay careful attention to the stereochemistry of the product.
1. NaNH2 2. CH3CH2Br

HNO3/H2SO4

H2O, H2SO4 HgSO4

Br

KOH, heat
Br

O H H O OMe OMe heat

2. Complete the following reactions. Pay careful attention to the stereochemistry of the product.

Na/NH3

heat

OMe

Br2 FeBr3

3. Provide a detailed mechanism for the following reaction using a curved arrow notation.
Br

HBr

4. How would you complete the following synthesis? You may use acetylene, additional alkyl halide (up to 2 carbons units) and any necessary reagents.

5. a. Draw the structure of the active electrophile in the nitration of benzene

b. Draw the most important resonance contributor that explain why the amino group is an ortho director.

c. Draw the thermodynamic product of addition of HBr to 1,3 butadiene.

d. Draw a schematic representation of the HOMO in 1,3-butadiene.

6. Label each of the following compounds as being aromatic or non-aromatic.


O H

1. (10 pt.) What will be the major product of the following reactions? Pay careful attention to the stereochemistry of the product.

1.O3 2. (CH3)2S

OO

1. AlCl3 Cl O 2. H2O, H+

Na/NH3

OMe Cl AlCl3 MeO

O heat

2. (18 pt.) Complete the following reactions. Pay careful attention to the stereochemistry of the product.
3 pt. NaNH2 Na 1.

HO

2. H+

4 pt. CO2CH3

heat

CO2CH3

CO2CH3

2 pt.

HNO3/H2SO4 NO2

NO2

4 pt. heat only 3 points if two identical molecules instead of one 3 pt. NBS h Br

+
Br

Br

2 pt.

heat

no reactionthe diene is "locked" into trans conformation

3. (10 pt.) Complete the following sentences using the hypothetical reaction energy diagram provided below.

a. b. c.

The intermediate in this reaction is represented by the letter ___c___ The kinetic product of this reaction is represented by the letter ____f____ The transition state the that leads to the thermodynamic product is represented by the letter ___d____ The conversion of __c___ to __f (or e)___ has the highest rate constant. Cooling of the kinetic product will give the thermodynamic product (true/ false).

d. e.

4. (12 pt.) How would you complete the following synthesis? You may use any necessary reagents.

HO OH

Br H H NaNH2 H Na H

NaNH2

Na

Br

H2 Lindlar cat.

KMnO4 or OsO4 HO OH

5. (8 pt.) a. (3. pt) Cyclopentadiene is not aromatic. When the molecule is reacted with Na it is converted to an aromatic molecule. Draw the structure of the product.

b. (3 pt.) Circle the molecule that show the longest wavelength absorption for the n to * transition.
O O

c. (2 pt.) b. Draw the most important resonance contributor that explains why bromo benzene is a para director

Br

6. (12 pt.) Provide a detailed mechanism for the following reaction using a curved arrow notation. You dont need to show the arrow pushing for the reaction with the MCPBA itself.

OH

MCPBA

OH MCPBA
H O H

OH O
H H O

H (MCPBA is an acid...) H O

OH
H O H

OH O H

Chem 140B

Chem 140B
KEY: ++ strong emphasis in lecture + partial coverage (pay attention to emphasis in lecture) no coverage in lecture

The "Chemical Highlight" sections are for your enjoyment and are highly recommended. Yet, you do not need the information for the exams.
Course Home Syllabus Calendar TA Assignments Exams Suggested Reading

10

Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure + ++ ++ ++

10-1 Physical and Chemical Tests 10-2 Defining Spectroscopy 10-3 Proton Nuclear Magnetic Resonance 10-4 Using NMR Spectra to Analyze Molecular Structure: The Proton Chemical Shift 10-5 Tests for Chemical Equivalence 10-6 Integration 10-7 Spin-Spin Splitting: The Effect of Nonequivalent Neighboring Hydrogens 10-8 Spin-Spin Splitting: Some Complications 10-9 Carbon-13 Nuclear Magnetic Resonance

++ ++ ++

+ +

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Study%20Materials.html (1 of 7)9/4/2007 7:22:51 AM

Chem 140B

11

Alkenes and Infrared Spectroscopy + ++ ++ ++ ++ ++

11-1 Naming the Alkenes 11-2 Structure and Bonding in Ethene: The Pi Bond 11-3 Physical Properties of Alkenes 11-4 Nuclear Magnetic Resonance of Alkenes 11-5 Infrared Spectroscopy 11-6 Degree of Unsaturation: Another Aid to Identifying Molecular Structure 11-7 Catalytic Hydrogenation of Akenes: Relative Stability of Double Bonds 11-8 Preparation of Alkenes from Haloalkanes and Alkyl Sulfonates: Bimolecular Elimination Revisited 11-9 Preparation of Alkenes by Dehydration of Alcohols

++

++

12

Reactions of Alkenes ++

12-1 Why Addition Reactions Proceed: Thermodynamic Feasibility 12-2 Catalytic Hydrogenation 12-3 Nucleophilic Character of the Pi Bond: Electrophilic Addition of Hydrogen Halides 12-4 Alcohol Synthesis by Electrophilic Hydration: Thermodynamic Control 12-5 Electrophilic Addition of Halogens to Alkenes 12-6 The Generality of Electrophilic Addition

++ ++

++

++ ++

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Study%20Materials.html (2 of 7)9/4/2007 7:22:51 AM

Chem 140B

12-7 Oxymercuration-Demercuration: A Special Electrophilic Addition 12-8 Hydroboration-Oxidation: A Stereospecific AntiMarkovnikov Hydration 12-9 Diazomethane, Carbenes, and Cyclopropane Synthesis 12-10 Oxacyclopropane Synthesis: Oxidation by Peroxycarboxylic Acids 12-11 Vicinal SYN Dihydroxylation with Osmium Tetroxide 12-12 Oxidative Cleavage: Ozonolysis 12-13 Radical Additions: Anti-Markovnikov Product Formation 12-14 Dimerization, Oligomerization, and Polymerization of Alkenes 12-15 Synthesis of Polymers 12-16 Ethene: An Important Industrial Feedstock 12-17 Alkenes in Nature: Insect Pheromones

++

++

+ +

+ -

13

Alkynes: The Carbon-Carbon Triple Bond + ++ ++ ++ ++

13-1 Naming the Alkynes 13-2 Properties and Bonding in the Alkynes 13-3 Spectroscopy of the Alkynes 13-4 Preparation of Alkynes by Double Elimination 13-5 Preparation of Alkynes by Alkylation of Alkynyl Anions

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Study%20Materials.html (3 of 7)9/4/2007 7:22:51 AM

Chem 140B

13-6 Reduction of Alkynes: The Relative Reactivity of the two Pi Bonds 13-7 Electrophilic Addition Reactions of Alkynes 13-8 Anti-Markovnikov Additions to Triple Bonds 13-9 Chemistry of Alkenyl Halides and Cuprate Reagents 13-10 Ethyne as an Industrial Starting Material 13-11 Naturally Occurring and Physiologically Active Alkynes

++

++ ++ ++ -

14

Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy + ++ +

14-1 Overlap of Three Adjacent Orbitals: Electron 14-2 Radical Allylic Halogenation 14-3 Nucleophilic Substitution of Allylic Halides: Kinetic and Thermodynamic Control 14-4 Allylic Organometallic Reagents: Useful ThreeCarbon Nucleophiles 14-5 Two Neighboring Double Bonds: Conjugated Dienes 14-6 Electrophilic Attack on Conjugated Dienes 14-7 Delocalization Among More Than Two Pi Bonds: Extended Conjugation and Benzene 14-8 A Special Transformation of Conjugated Dienes: Diels-Alder Cycloaddition 14-9 Electrocyclic Reactions 14-10 Polymerization of Conjugated Dienes: Rubber

++ ++ ++

++

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Study%20Materials.html (4 of 7)9/4/2007 7:22:51 AM

Chem 140B

14-11 Electronic Spectra: Ultraviolet and Visible Spectroscopy

++

15

Benzene and Aromaticity: Electrophilic Aromatic Substitution + ++

15-1 Naming the Benzenes 15-2 Structure and Resonance Energy of Benzene: A First Look at Aromaticity 15-3 Pi Molecular Orbitals of Benzene 15-4 Spectral Characteristics of the Benzene Ring 15-5 Polycyclic Benzenoid Hydrocarbon 15-6 Other Cyclic Polyenes: Hckels Rule 15-7 Hckels Rule and Charged Molecules 15-8 Synthesis of Benzene Derivatives: Electrophilic Aromatic Substitution 15-9 Halogenation of Benzene: The Need for a Catalyst 15-10 Nitration and Sulfonation of Benzene 15-11 Friedel-Crafts Alkylation 15-12 Limitations of Friedel-Crafts Alkylations 15-13 Friedel-Crafts Alkanoylation (Acylation)

+ ++ + ++ ++ ++

++ + ++ + +

16

Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Study%20Materials.html (5 of 7)9/4/2007 7:22:51 AM

Chem 140B

16-1 Activation or Deactivation by Substituents on a Benzene Ring 16-2 Directing Inductive Effects of Alkyl Groups 16-3 Directing Effects of Substituents in Conjugation with the Benzene Ring 16-4 Electrophilic Attack on Disubstituted Benzenes 16-5 Synthetic Strategies Toward Substituted Benzenes 16-6 Reactivity of Polycyclic Benzenoid Hydrocarbons 16-7 Polycyclic Aromatic Hydrocarbons and Cancer

++

++ ++

+ -

17

Aldehydes and Ketones: The Carbonyl Group + ++ ++ ++ ++

17-1 Naming the Aldehydes and Ketones 17-2 Structure of the Carbonyl Group 17-3 Spectroscopic Properties of Aldehydes and Ketones 17-4 Preparation of Aldehydes and Ketones 17-5 Reactivity of the Carbonyl Group: Mechanisms of Addition 17-6 Addition of Water to Form Hydrates 17-7 Addition of Alcohols to Form Hemiacetals and Acetals 17-8 Acetals as Protecting Groups 17-9 Nucleophilic Addition of Ammonia and Its Derivatives 17-10 Deoxygenation of the Carbonyl Group

++ ++

++ ++

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Study%20Materials.html (6 of 7)9/4/2007 7:22:51 AM

Chem 140B

17-11 Addition of Hydrogen Cyanide to Give Cyanohydrins 17-12 Addition of Phosphorus Ylides: The Wittig Reaction 17-13 Oxidation by Peroxycarbolic Acids: The BaeyerVilliger Oxidation 17-14 Oxidative Chemical Tests for Aldehydes

++ ++ -

++

18

Enols, Enolates, and the Aldol Condensation: ,Unsaturated Aldehydes and Ketones ++ ++ ++ ++ ++

18-1 Acidity of Aldehydes and Ketones: Enolate Ions 18-2 Keto-Enol Equilibria 18-3 Halogenation of Aldehydes and Ketones 18-4 Alkylation of Aldehydes and Ketones 18-5 Attack by Enolates on the Carbonyl Function: Aldol Condensation 18-6 Crossed Aldol Condensation 18-7 Intramolecular Aldol Condensation 18-8 Properties of ,-Unsaturated Aldehydes and Ketones 18-9 Conjugate Additions to ,-Unsaturated Aldehydes and Ketones 18-10 1,2- and 1,4-Additions of Organometallic Reagents 18-11 Conjugate Additions of Enolate Ions: Michael Addition and Robinson Annulation

++ ++ ++ ++

+ ++

Course Home | Syllabus | Calendar | Assignments | Exams | Suggested Reading

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Study%20Materials.html (7 of 7)9/4/2007 7:22:51 AM

Chem 140B

Chem 140B
Date Week 1 Topic Nuclear Magnetic Resonance spectroscopy Chapter(s) 10 11-12 12 13 14 15 16 17 17 18 10-18

Week 2 Alkenes and Infra Red Week 3 Alkenes reactions Week 4 10/18/04 (M) Midterm Examination # 1 Alkynes Week 5
Course Home Syllabus Calendar TA Assignments Exams Suggested Reading

Delocalized Pi systems and UV spectroscopy

Week 6 Benzene and Aromaticity Week 7 Electrophilic aromatic substitution Week 8 11/15/04 (M) Midterm Examination # 2 Aldehydes and Ketones Week 9 Aldehydes and Ketones Week 10 Enol, Enolates and aldol condensation Final Examination (comprehensive)

December 8, 3:00 6:00 pm.

Course Home | Syllabus | Calendar | Assignments | Exams | Suggested Reading

http://chem-courses.ucsd.edu/CoursePages/UpperDiv/140B_Weizman/Calendar.html9/4/2007 7:22:01 AM

Chemistry 140B Course Syllabus, Spring 2007


Section Lecture B01 B02 B03 B04 B05 B06 B07 B08 Meets MWF 8:00-8:50 M 9:00-9:50a M 10:00-10:50a Tu 2:00-2:50p W 9:00-9:50a W 10:00-10:50a W 12:00-12:50p F 2:00-2:50p F 3:00-3:50p Room Peter 108 APM 2301 APM 2301 SEQUO 148 CSB 004 CSB 004 WLH 2113 SOLIS 109 SOLIS 109 TA Bob Ternansky Silas Chiu Silas Chiu Silas Chiu Siu-Ling Sit Carla Kwon Ginsa Wu Rachel Scanza Yuen Wei e-mail rjt@ucsd.edu scchiu@ucsd.edu scchiu@ucsd.edu scchiu@ucsd.edu ssit@ucsd.edu ckwon@ucsd.edu gjwu@ucsd.edu rscanza@ucsd.edu ytwei@ucsd.edu

Instructor: Dr. Bob Ternansky NSB 2303A-3 e-mail: rjt@ucsd.edu (Phone: 858-534-6416) Office Hours: Wednesdays: 9:00AM (NSB2303-A3) Thursdays: 6:20PM (outside Center 109) Always: Mutually available times by appointment....just send request by e-mail Always check Discussion forum prior to attending office hours for last minute changes! Current Course Information: Please check the course web page (www.webct.ucsd.edu) regularly for information and frequent updates regarding this course. Texts: (1)Organic Chemistry Structure and Function, 4th or 5th Ed.; by Vollhardt and Schore; W. H. Freeman and Co.; 2003 or 2006. (2) Study Guide and Solutions Manual for Organic Chemistry Structure and Function, 4th or 5th Ed.; by Schore; W. H. Freeman and Co.; 2003 or 2006. (3) A molecular model kit is strongly recommended! See the web site for inexpensive sources of model kits. (4) Recommended: Pushing Electrons, a guide for students of organic chemistry; Daniel P. Weeks. For the main text, you are given the choice of using either edition since they are very similar. I will be teaching from the 5th edition but will provide all cross-reference information to the 4th edition (basically this will involve the homework assignments). My recommendation is that if you are buying a new book, get the 5th edition. If you are buying a used book, or already have a book, you will be OK with the 4th.

Homework: Homework problems will be assigned for each chapter. The assignments will be posted on the course web site. The homework will not be collected or graded. It will be your responsibility to work the problems assigned. This is a very important aspect of learning organic chemistry: the practice part. I strongly recommend that you work each of the problems more than once.three or four times each is not too much! The idea is to get practice at solving the problems based on the concepts presented in lecture and in the chapter. You should also work through all of the exercises presented throughout the chapter. The exam questions will be based in large part on homework and exercise problems. Working the problems only once is like trying to shoot a free throw once and then expecting to do well in a basketball game. If you have intentions of obtaining an A in this course; practice, practice, practice is the way to do it!

Exams: Three midterms (lowest to be dropped) will be given during regularly scheduled class time on the dates specified (see course calendar). The final exam will take place on Friday, June 15, 2007 from 8:00-11:00 AM. Make sure that you do not have conflicts for the midterms or the final exam!!! No make-up's will be given. For all exams, you must present a picture ID to take the exam. No calculators or cell phones will be allowed during exams. No crib sheets or notes will be allowed. If you need to leave the room during the exam, you will be asked to remove all items from your pockets before leaving. All exams should be written in INK. If you choose to use pencil, NO re-grades will be considered. If you wish to ask for a re-grade (and you took your exam in ink), do not write anything on the exam but present it to your TA in person with your question. Note that a request for a re-grade will involve a re-grade of the entire exam. The possibility exists that this will result in you score being lower following the re-grade. All exam grades will be considered final one week after the return of the exams to the students (ie, no re-grades after this time). All students are encouraged to review the university's policy on academic dishonesty. All incidents of suspected academic dishonesty will be taken seriously and reported to the appropriate dean according to university guidelines. I strongly recommend that you do not consider cheating as I do not appreciate dealing with such situations.

Grading: The course grade will be based on points earned from performance on two midterm exams and one final exam. The course will be graded on a curved grading system for the benefit of the students. However, if you obtain 510 points or more in the course (out of 600 total), you will be guaranteed a grade of A, regardless of the curve. This will allow for the possibility that all students in the class may theoretically obtain an A (on a curved system, even if all students scored above 510, some would fail!!!). NO other grades will be guaranteed with point values. ALL other grades (from A minus to F) will be assigned on a curve of the FINAL total points. NO LETTER GRADES can be assigned to midterm exam results so please do not ask. Three midterms will be given. The lowest of the three scores on the midterms will be dropped. Each midterm will be

worth 150 points and the total possible points for the midterms will be 300. The final will be worth 300 points. The exam schedule and point assignments are listed below:

Item Midterm #1 Midterm #2 Midterm #3 Final TOTAL

Date 4/16/07 5/7/07 5/30/07 6/15/07

Total 150* 150* 150* 300 600

* lowest midterm exam score dropped

How to do well in O-Chem: Organic chemistry is unlike most other topics you have studied. As such, it requires different study techniques. You should always read the material to be covered in class prior to the lecture. Following the lecture, read the material again. When you read, be sure that you have a pen or pencil in hand and write as you read. Work all exercises that appear throughout the chapter and work all of the assigned problems. Proficiency in organic chemistry requires practice, practice, practice and very little memorization. With practice, you will be able to draw structures rapidly, devise resonance contributors and come up with reaction mechanisms. If you merely read the material passively, you will not succeed. This is similar to reading a book on golf and expecting to shoot par your first time on the course. It just won't happen...you need a lot of practice! You also can't hit the ball around the night before a tournament and expect to do well the next day. Excellence in many sports is the result of cumulative skill development. The same goes for organic chemistry. Finally, do not procrastinate. Cramming for an O-chem exam does not work! I have had straight A students fail this course because they chose to disregard the previous statement. There is simply too much material and too many hours of practice required to get it all done a few days before an exam. As a rule of thumb, you should spend at least 4-5 hours of study time per hour of lecture. Thus, in one week you should set aside 12-15 hours for the study of organic chemistry. If you cannot afford this time commitment, it would be advisable for you to not take the class until you have the time. This class requires a serious commitment and anything less will be clearly reflected in your final grade. Organic chemistry requires visualization for the understanding of concepts. Your text has an excellent web site that provides graphics that can greatly help in this process. In addition, the use of molecular models is very important, especially for the understanding of stereochemistry. It is very rare that a person can visualize the three-dimensional

aspects of organic compounds without the aid of models. You will need to learn to do this (visualize without models) but practicing with models can really help. You will not be permitted to use models on the exams. Over the years, I have noticed that many students do a poor job of taking notes in class. Since the test material comes from the topics I stress in class, if you miss something in your notes, there is a good possibility that you will miss some test questions. If your notetaking skills are inadequate you may want to tape record the lecture or compare your notes with a friend. If you miss a lecture or are missing notes on a particular topic, check with your classmates to get the appropriate notes. The exams are structured to test your understanding of the material, not your ability to regurgitate facts. For this reason, the exam questions will usually not look too familiar to you. This can cause some students undue angst. Your job is to be able to take what you have learned and to apply it to new situations.thats what applied science is all about! So I recommend that you practice for this by reserving a few homework problems to do under a simulated test situation. That is, prepare a test for yourself of problems that you havent seen before that you work within a limited amount of time. This will be good practice for the exams.

Class Schedule: What follows is a schedule of class lectures. We will be covering chapters 10 through 18 of the text. This represents a significant amount of material so it is important that you do not fall behind! The lectures will approximately follow the schedule indicated; however the exam dates will NOT change. The exams will cover all the material discussed up to and including the lecture prior to the exam. Midterm #1, #2, and #3 will NOT be cumulative. The final exam WILL be cumulative. The final exam will be weighted toward previously untested material.

140-B Class Schedule Spring 2007 Monday April 2 Ch. 10 April 9 Ch. 11 April 16 Midterm #1 April 23 Ch. 13 April 30 Ch. 14 May 7 Midterm #2 May 14 Ch. 16 May 21 Ch. 17 May 28 HOLIDAY June 4 Ch. 18 June 11 June 12 June 5 May 29 May 22 May 15 May 8 May 1 April 24 April 17 April 10 Tuesday April 3 Wednesday April 4 Ch. 10 April 11 Ch. 11 April 18 Ch. 12 April 25 Ch. 13 May 2 Ch. 14+15 May 9 Ch. 15 May 16 Ch. 16 May 23 Ch. 17 May 30 Midterm #3 June 6 Ch. 18 June 13 June 14 June 7 May 31 May 24 May 17 May 10 May 3 April 26 April 19 April 12 Thursday April 5 Friday April 6 Ch. 10+11 April 13 Ch. 12 April 20 Ch. 12+13 April 27 Ch. 14 drop date no "W" May 4 Ch. 15 May 11 Ch. 16 May 18 Ch. 16+17 May 25 Ch. 17 June 1 Ch. 18 drop with "W" June 8 Ch. 18 June 15 Final 8:00-11:00

1. Dept./Course Name/Number: Dept. of Chemistry and Biochemistry Organic Chemistry II/CHEM 140B 2. Course (Catalogue) Description: A continuation of 140A; acid/base reactions, chemistry of the carbonyl group, sugars, peptides, nucleic acids and other natural products. 3. Prerequisite(s): Chem. 140A 4. Course Textbook(s): Organic Chemistry: Structure and Function, 5th ed., Vollhardt & Schore 5. Course Objectives: Second of three-quarter sequence in organic chemistry for science and engineering majors 6. Course Topics: See course (catalogue) description 7. Implementation (lecture, discussion, lab hours, etc): 3 hrs lecture, 1 hr discussion per week Methods of evaluation (homework, midterms, etc): Homework, exams, final exam

8. & 9. In the following, we list a set of desired course outcomes and address how such outcomes are accomplished and assessed.
Desired Outcome Emphasis: 0 = not addressed 1 = Addressed but not emphasized 2 = Emphasized 1 Method(s) used to address Assessment: 0 = not assessed 1 = assessed Method(s) used to assess

Apply knowledge of math and physics

What little math is needed in this course is covered in lecture or readings

Design and conduct experiments as well as to analyze and interpret data Design a system, component or process to meet desired needs Function on multidisciplinary teams Ability to identify, formulate and solve engineering problems Understanding of professional and ethical responsibility Communicate effectively Broad education necessary to understand the impact of engineering solutions in a global and societal context Recognition of need for and ability to engage in life long learning Contemporary issues

1 0

Work in groups in discussion section

0 0

Lecture emphasizes how science is changing Many contemporary issues can be addressed in the context of organic chemistry lecture and readings

Use techniques, skills and tools necessary for engineering practice

10. Preparer/Date of Preparation: Barbara Sawrey; May 30, 2007

You might also like