Welcome to CHM 252 ORGANIC CHEMISTRY- II

Dr. Sivappa Rasapalli

CHM 252 Logistics

Instructor: Professor Sivappa Rasapalli Office: Violette Research Building 216 Office telephone: 508-999-8276 E-mail: srasapalli@umassd.edu Class hours: Monday, Wednesday and Friday 89.00 AM (DION 116) Recitations: Friday 2-3 (SE#305) / 3-4 (SE#305) / 4-5 PM (SE#210) Office hours: Monday, Wednesday & Friday 9-10AM Tuesday & Thursday 10-11AM

Instructor : Dr. Sivappa Rasapalli

Education: MSc.Ed. Chemistry, 1995, RIEM, NCERT MEd. Chemical Education, 1997, RIEM & KSOU Mysore Ph.D. Chemistry, 2003, NCL Postdoc: Supramolecular & Cage Hydrocarbon Chemistry, 2004, UNT; Organic Synthesis & Methods Development, 2007, UTA; Bioengineering & Drug Delivery, 2008, HST (Harvard-MIT). Research interests: Synthesis of medicinally intriguing and synthetically interesting Natural products; Heterocyclic Chemistry; Green Chemistry; Development of novel methodologies; Catalysis (enzymatic, organo and organometallic); Development of novel biomaterials for bioengineering and drug delivery; Chemical education - Development of novel educational tools and technology with an emphasis on Green Chemistry

My CHM 252 Schedule

Time Monday Organic Chemistry 252 Tuesday Wednesday Organic Chemistry 252 Thursday Friday Organic Chemistry 252 8:00 -9.00 am

9:00 -10.00am 10:00-11 am 11:00-12 Pm 12:00-1.00 pm 1:00-2.00 pm 2:00-3.00 pm

Office Hours Office Hours

Office Hours Office Hours

Office Hours

Research Lab Textile #108

Organic Chemistry 252-02R1 Organic Chemistry 252-02R2

3:00-4.00 pm 4:00 -5.00 pm 5:00-6.00 pm

Recitations
Friday 2-3 PM ; 3-4PM; 4-5PM Recitation: you are required to enroll in the recitation section. The recitation sections will be utilized for development and elaboration of basic concepts developed in lecture through the use of animation and molecular modeling, in addition to providing an interactive forum for addressing student questions about lecture material, assigned readings and problem sets. Attendance at the assigned recitation section is must and you are strongly encouraged to take advantage of this resource.

The quizzes are held in recitations unannounced!

NOTE: Students who do not show up to classes and recitations will not be allowed to take up the exams and quizzes!

Course Website
Check it up under my courses https://mycourses.umassd.edu/webapps/portal/frameset.jsp?tab_tab_group_id=_2_1& url=%2Fwebapps%2Fblackboard%2Fexecute%2Flauncher%3Ftype%3DCourse%26i d%3D_43600_1%26url%3D Faculty web page https://www.umassd.edu/cas/chemistry/facultyampstaff/sivapparasapalli/

Textbooks and Other Materials

Textbook: McMurry, Organic Chemistry, 8th edition, (Earlier editions are OK) Brooks/Cole Online OWL homework program for McMurry Organic Chemistry Models Kit Optional PRS will be used

About CHM 252

This course is the second part of a two-course sequence designed to introduce students to the theoretical underpinnings of organic chemistry. This course is intended for biology, chemistry and premedical majors. In Organic II our focus shifts to the chemistry of alcohols, carbonyl compounds, amines and other biologically important compounds, including small biomolecules: carbohydrates, and amino acids. Structure, properties, reactions and mechanisms of these compounds as well as their occurrence and biochemical roles in nature will be emphasized. You will learn more about spectroscopic techniques used to determine molecular structure. A solid understanding of Organic Chemistry II will provide you with an excellent background for future courses such as Biochemistry, Molecular Biology, Applied Spectroscopy, and other advanced Chemistry courses (not to mention an edge on the MCAT or GRE).

Course objectives
Individuals who successfully complete 2 semesters of organic course will be able to: 1. Define and employ the vocabulary of organic chemistry. 2. Draw correct structural representations of organic molecules. 3. Write reasonable transformations of all compounds. 4. Employ stereochemical considerations when analyzing mechanisms and transformations. 5. Understand the relations between the Structure of organic molecules and their reactivity 6. Show mastery over organic reaction patterns; mechanism of reactions; synthesis of organic compounds 7. Explain the details of success in organic synthesis-solvents, conditions and techniques 8. Know about Classical or Named Reactions and about Important Researchers 9. See how spectroscopy fits into the process 10. Enjoy the ability that organic chemists exercise to control at the atomic level 11. Understanding and illustrating the role of organic chemistry in biology, medicine, and industry

Grading Standards
Point Distribution: 1 Hour Examinations (4@ 100) Weekly Quizzes OWL Problem sets Final Examination TOTAL Assignment of Letter Grades:
(97 to 100%) (93 to 97%) (90 to 93%) (87 to 90%) (83 to 87%) (80 to 83%) (77 to 80%) (73 to 77%) (70 to 73%) (60 to 70%) less than 60%

300 pts (Lowest dropped) 100 pts 100 pts 100pts 200 pts (ACS std Exam for 50%) 800 pts
A+ A AB+ B BC+ C CD F

Course Calendar
Class Dates (MWF) Class Content: McMurry, Organic Chemistry, 7th or 8th Edition
Review on Fridays Recitation on 25th Weeks 1 and 2 weeks 3-5 Exam 1 Tuesday Feb 18th Spectroscopy & molecular structure, IR and MS (brief preview); NMR spectroscopy 12 and 13.1-13.13, 15.8, 17.11, 18.9, 19.14, 20.8, 21.10, 24.10 Alcohols, Phenols and Ethers, Aldehydes & Ketones 17.1--17.10 18.1-18.8, 19.1-19.14 (100Pts) Chapters 17, 18, 19, 12 and 13

week 6 week 7 week 8 Exam II Monday March 24th week 9 week 10 week 11 Exam III Wednesday April 23rd week 12 week 13 Exam IV Monday May 5th

Carboxylic Acids Carboxylic Acids Derivatives, Nitriles Carbonyl substitution (100Pts) Chapters 19-22

20.1-20.8 21.1- 21.10 22.1-22.7

Carbonyl condensation reactions 23.1-23.13 Amines 24.1-24.10 26.1-26.11

Biomolecules Part 1 (Amino Acids & Proteins) (100Pts) Chapters 23-26 Biomolecules Parts 2 Carbohydrates Over view of Pericyclic reactions 30.1-30.9 (100Pts) Chapters 25, 30

25.1-25.11

Final Exam Friday, May 9th, 8:00 am 11:00 am (Schedule from Registrar) Location Dion #116

Examination Dates (Tentative)

Exam 1 Tuesday Feb 18th Exam II Monday March 24th Exam III Wednesday April 23rd Exam IV Monday May 5th (100Pts) Chapters 13, 17-18 (100Pts) Chapters 18-22 (100Pts) Chapters 23-26 (100Pts) Chapters 25-27, 30

Friday, May 9th 8:00 am 11:00 am (Schedule by Registrar) Location Dion Sci & Engr 116 ; Coverage:

covered

Cumulative of all the chapters

Attendance
Regular attendance is mandatory - you may be dropped if you miss more than 9 hours of class.

Weekly Quizzes
1st Quiz 2nd Quiz3rd Quiz 4th Quiz 5th Quiz 6th Quiz NOTE: Only the scores from the best five of the quiz set will be counted toward the final course grade. Lowest will be dropped!

Grade Policy
Exams, Grading & Regrading: there will be four exams and one cumulative final. There are no re-exams and You are not allowed to drop any exam ( We drop the lowest...skipping any exam is not allowed). However, in case of illness, etc. with an appropriate excuse, given before rather than after the exam, a student may be allowed to miss and reschedule one exam. Re-grading must be done within two days from the time the exam is returned. Questions must be directed to the instructor/grader in writing. You must not re-write on your exam in any fashion until after it has been regraded. Drops, Withdrawals, or Incompletes: the deadlines for dropping or withdrawing must be rigorously observed. Final grades: Final exams are scheduled by the Registrars office. Students missing a final examination must obtain permission to take the make-up exam

Course policies:
Prerequisites, withdrawals and incompletes To be enrolled in this course, you must have passed CHM151/3, 152/4 and CHM251 (or the equivalent at another school) with a grade of C- or better. The last day to withdraw from this class and receive a grade of W is Friday, April 8th, so be sure to check on your average prior to then. Only students who are passing the course at the time of the final exam may request an incomplete (I). An incomplete will only be given under exceptional circumstances and if requested within 48 hours after the final exam. Failing the final will not be considered an acceptable reason to request an incomplete. Academic Dishonesty: Cheating in any form will not be tolerated. Anyone suspected by me of cheating will receive no credit for that assignment. For more information on what constitutes academic dishonesty consult the general catalog, p. 52, under Academic Ethical Standards. Hour exams in this class are to be entirely individual effort, no collaboration, no unauthorized notes or supple-mentary materials allowed. Collaboration and use of notes will be allowed on some quizzes.

Classroom policies:
Courtesy: Turn off your cell phone ringer during class time. Talking on the phone is not allowed in class. Phones must be off during exams unless you have an emergency situation. If you must make/answer a call or visit the rest room, please leave the room quietly. Its OK to bring food/drink to class as long as you take your trash with you when you leave. Please refrain from idle chit-chat; it detracts from others learning and is discouraged. Anyone who disrupts class or exhibits discourteous behavior may be asked to leave. No texting in class. Please do the mature thing and consider how your actions affect those around you.

Accommodations for Students with Disabilities:

Students with disabilities who may need accommodations in this class are encouraged to notify the instructor and contact Disabled Student Services & Programs early in the semester so that reasonable accommodations may be implemented as soon as possible.

Warning!
Organic Chemistry is difficult and challenging! Memorization alone does not help! Body of knowledge + application of theory = Success How to succeed? 1. read the text before lecture, and come prepared. 2. listen carefully to lectures 3. read the text (take notes) 4. do the homework (twice...?) 5. review Do not blame others for a bad grade. It is not an easy course! This is not a simple GPA boost course!

Recognize the symptoms and seek help!

There are chemistry terms heard or read that the mind does not fully comprehend, and that you did not encounter before! So how do you avoid the barrier of misunderstood words? Follow the following signs and seek help and get clarified! Use the office hrs, tutoring sessions!

Mind is Blank

Feeling dumb & not belonging

Irritable

Disgusted

CHM252 material is cumulative

STUDY TO UNDERSTAND THE MATERIAL The material keeps building on itself unlike any other subject - Its a net work and topics are inter-related! ANYTHING THAT YOU DO NOT MASTER WILL COME BACK TO HAUNT YOU LATER! You literally cannot forget anything in this course, and cannot skip any chapter or topic as they are interconnected. Review the basic concepts of CHM251 before the 1st week, and take the review exam to see what needs to be fixed, and where do you stand!

Review Exam is on Pre-requisites

Review Exam will be held in the first recitation section. You are expected, at the least, to: know basic terminology for organic chemistry recognize and name the major functional groups write systematic names draw accurate structures correlate molecular structure with physical & chemical properties categorize reactions by type write reaction mechanisms correlate energy changes with molecular structure changes

Additional Hints
1) Attend the Lectures; Understanding concepts is essential 2) Keep up with the material; Relatively low factual content 3) Review and rewrite your lecture notes after every lecture 4) Prepare flash cards for key concepts and reactions/mechanisms 5) Form study groups , but try not to depend on others 6) Solve problems at the end of the chapter that correspond to the lecture material 7) Don't cram for exams; Value of the subject lies in application of concepts (problem solving) 8) Lectures: presentation of key facts and concepts only! 9) The average student should spend about eleven hours per week studying for this course (for example, one hour each weeknight, three hours each Saturday, and three hours each Sunday). But do not force 11hrs on a single day. Daily reading is indispensable for the success HOW TO STUDY ORGANIC CHEMISTRY: Check it out at http://chemistry.umeche.maine.edu/CHY251/howto.html

Expectations for Students

In order to succeed in the course objectives, * * you must : attend classes regularly read the text and lecture notes before the corresponding class meeting take an active part in class, answer and ask questions solve problems: work through all the assigned homework in OWL; try textbook problems make use of the Study Guide for answers all text problems make lists of concepts and problems you don't understand bring your list to my office or the study room if problems remain unresolved after that, e-mail them to me * * you must use technology: consult the class home pages (they will be set up) use e-mail to communicate with the instructor and with fellow students notes and some assignments will be distributed and returned by e-mail a class discussion list will collect questions, answers, and other discussions Use OWL to learn the concepts ; Use PRS (i-clickers) to self evaluate

Expectations for the Instructor

In order to help you succeed in the course objectives, * * I will : attend class regularly coordinate in-class activities; clarify and reinforce the concepts that you encounter in the text and in the lecture; supply my notes * * I will provide appropriate resources: details of how the class works lecture handouts through emails homework assignments conduct quizzes and exams suggestions and outside resources * * I will give you feedback: respond promptly to e-mail questions promptly return quizzes and exams provide regular assessment of your progress in the course upon request

Common Reasons for failure

Lack of organization Difficulty in keeping up with lecture while taking notes Failure to finish exams Inability to manipulate three-dimensional structures on paper Too little drill lack of repetitive practice Falling behind Poor problem analysis Inability to see and mentally manipulate three-dimensional objects Insufficient energy and/or motivation for the challenges of this course

Collective Advice to do well in OCHM

GOOD LUCK!
Organic Chemistry may be the best Liberal Arts class you will ever take!!
"It is not so very important for a person to learn facts, for that he doesn't really need a college education, for he can learn them from books. The value of an education in a liberal arts college is not the learning of many facts but the training of the mind to think, something that cannot be learned from books." Albert Einstein

Look Forward to a wonderful semester!

Chapter 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy 1. 2. 3. 4. 5. 6. 7. Nuclear Magnetic Resonance Spectroscopy applications The Nature of 1 H NMR ( proton NMR)Absorptions Characteristics of Chemical Shifts in 1H NMR Spectroscopy Uses of 1 H NMR Spectroscopy 1 H NMR Spectroscopy and Proton Equivalence Integration of 1H NMR Absorptions: Proton Counting SpinSpin Splitting in 1H NMR Spectra

Chapter 17: Alcohols and Phenols. 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. Naming Alcohols and Phenols Properties of Alcohols and Phenols: Hydrogen Bonding Properties of Alcohols and Phenols: Acidity and Basicity Preparation of Alcohols from Reduction of Carbonyl Compounds Preparation Alcohols from Reaction of Carbonyl Compounds with Grignard Reagents Reactions of Alcohols Oxidation of Alcohols Protection of Alcohols Preparation and Uses of Phenols Reactions of Phenols

Chapter 18: Ethers and Epoxides; Thiols and Sulfides only the following topics would be touched upon while chapter 17 is covered 1. The Williamson Ether Synthesis 2. Ring-Opening Reactions of Epoxides

Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions 1. 2. 3. 4. 5. 6. 7. 8. Naming Aldehydes and Ketones Nucleophilic addition of Grignard and hydride reagents Preparation of Aldehydes and Ketones Oxidation of Aldehydes and Ketones Nucleophilic Addition Reactions of Aldehydes and Ketones Relative Reactivity of Aldehydes and Ketones Nucleophilic Addition of H2O: Hydration Nucleophilic Addition of HCN: Cyanohydrins

9. 10. 11. 12. 13. 14. 15.

Nucleophilic Addition of Grignard Reagents and Hydride Reagents Nucleophilic Addition of Amines: Imine and Enamine Formation Nucleophilic Addition of Hydrazine: The WolffKishner Reaction Nucleophilic Addition of Alcohols: Acetal Formation Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction The Cannizzaro Reaction Conjugate Nucleophilic Addition to , -Unsaturated Aldehydes and Ketones

Chapter 20: Carboxylic Acids. 1. Naming Carboxylic Acids 2. Structure and Physical Properties of Carboxylic Acids 3. Dissociation of Carboxylic Acids 4. Substituent Effects on Acidity 5. Substituent Effects in Substituted Benzoic Acids 6. Preparation of Carboxylic Acids 7. Reactions of Carboxylic Acids Chapter 21: Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions 1. Naming Carboxylic Acid Derivatives 2. Nucleophilic Acyl Substitution Reactions 3. Nucleophilic Acyl Substitution Reactions of Carboxylic Acids 4. Chemistry of Acid Halides, Acid Anhydrides, Esters, Amides, and Nitriles Chapter 22: Carbonyl Alpha-Substitution Reactions 1. Keto-Enol Tautomerism 2. Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions 3. Alpha Halogenation of Aldehydes and Ketones 4. Alpha Bromination of Carboxylic Acids: The HellVolhardZelinskii Reaction 5. Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation 6. Reactivity of Enolate Ions 7. Halogenation of Enolate Ions: The Haloform Reaction 8. Alkylation of Enolate Ions Chapter 23: Carbonyl Condensation Reactions 1. 2. 3. 4. 5. Mechanism of Carbonyl Condensation Reactions Condensations of Aldehydes and Ketones: The Aldol Reaction Carbonyl Condensation Reactions versus Alpha-Substitution Reactions Dehydration of Aldol Products: Synthesis of Enones Using Aldol Reactions in Synthesis

6. Mixed Aldol Reactions 7. Intramolecular Aldol Reactions 8. The Claisen Condensation Reaction 9. Mixed Claisen Condensations 10. Intramolecular Claisen Condensations: The Dieckmann Cyclization 11. The Michael Reaction and The Stork Enamine Reaction 12. Carbonyl Condensation Reactions in Synthesis: The Robinson Annulation Reaction Chapter 24: Amines. 1. Naming Amines 2. Structure and Bonding in Amines 3. Properties and Sources of Amines 4. Basicity of Amines 5. Basicity of Substituted Arylamines 6. Synthesis of Amines 7. Reactions of Amines 8. Reactions of Arylamines 9. Tetraalkylammonium Salts as Phase-Transfer Catalysts Chapter 25: Biomolecules: Carbohydrates 1. Classification of Carbohydrates 2. Configurations of Monosaccharides: Fischer Projections 3. d,l Sugars 4. Configurations of the Aldoses 5 Cyclic Structures of Monosaccharides: Hemiacetal Formation 6. Monosaccharide Anomers: Mutarotation 7. Reactions of Monosaccharides 8. Disaccharides 9. Polysaccharides Chapter 26: Biomolecules: Amino acids, Peptides, and Proteins 1. Structures of Amino Acids 2. Isoelectric Points 3.Synthesis of Alpha-Amino Acids 4. Resolution of R,S Amino Acids 5. Peptides and Proteins 6. Covalent Bonding in Peptides 7. Synthesis of Peptides 8. Automated Peptide Synthesis: The Merrifield Solid-Phase Technique Protein Structure

Chapter 30: Pericyclic reactions 1. Molecular orbitals of conjugated Pi systems 2. Electrocyclic reactions 3. Cycloaddition reactions 4. Stereochemistry of cycloaddition reactions 5. Sigmatropic rearrangements 6.Rules for pericyclic reactions