Organic Chemistry CHEM 2370
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This 10 page Class Notes was uploaded by Neva McGlynn DVM on Sunday October 25, 2015. The Class Notes belongs to CHEM 2370 at University of North Texas taught by Sushama Dandekar in Fall. Since its upload, it has received 182 views. For similar materials see /class/229219/chem-2370-university-of-north-texas in Chemistry at University of North Texas.
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Date Created: 10/25/15
CHEM237O Solomons Chapter 10 9 ed CHAPTER 10 RADICAL REACTIONS INTRODUCTION RELATIVE STABILITIES OF RADICALS HALOGENATION OF ALKANES REACTIVITY v SELECTIVITY RADICAL ADDITION OF HBr TO ALKENES ANTI MARKOVNIKOV REGIOCHEMISTRY CHEM237O Solomons Chapter 10 9 ed DANDEKAR INTRODUCTION SOME REACTIONS OCCUR VIA RADICAL INTERMEDIATES R 0 HOW ARE RADICALS PRODUCED MLYSIS OR HETEROLYSIS HOW DO RADICALS REACT REACT WITH A MOLECULE TO GENERATE A m RADICAL SEE eg 91112 REACT WITH ANOTHER RADICAL TO FORM A MOLECULE RADICAL COUPLING SEE I39m RELATIVE STABILITIES USE BOND DISSOCIATION ENERGIES SEE TABLE 43 DO PROBLEM m WHICH c H BOND BREAKS MOST EASILY IN THE FOLLOWING MOLECULE CH32CH CH2 CH3 CHEM237O Solomons Chapter 10 9 ed DANDEKAR RELATIVE STABILITY OF ALKYL RADICALS SIMILAR TO CARBOCATIONS 3 gt 2 gt 1 gt METHYL DO PROBLEM l s4 HALOGENATION OF ALKANES SEE In MULTIPLE SUBSTITUTION I WHY PRODUCT OF FIRST SUBSTITUTION IS m REACTIVE THAN THE STARTING ALKANE I RADICAL CHAIN MECHANISE SEE r 1 INITIATION En ONLY A FEW MOLECULES OF CI2 UNDERGO HOMOLYTIC CLEAVAGE THIS WAY THEN AFTERA CI ARE PRODUCED STEPS amp I START CHEM237O Solomons Chapter 10 9 ed DANDEKAR 2 PROPAGATION STEPS I amp I OF THE PRODUCT IS FORMED IN El E I amp I ARE REPEATED OVER amp OVER UNTIL ALL STARTING MATERIALS ARE CONSUMED NOTE RADICALS ON BOTH SIDES OF eq 3 TERMINATION SEE RADICAL COUPLING REMOVES REACTIVE INTERMEDIATES THAT CAN PROPAGATE THE REACTION HAVE THE EFFECT OF TERMINATING THE REACTION ENERGY OF ACTIVATION FOR THESE REACTIONS IS USUALLY U 24 CHEM237O Solomons Chapter 10 9 ed DANDEKAR REACTIVITY v SELECTIVITY SEE r REACTIVITY SELECTIVITY F2 VERY HIGH NONE EASILYABSTRACTS ANY TYPE OF H FROM CH BOND Clz HIGH NONE Brz EASE OF ABSTRACTION I H gt I H gt I H gt H IN STEP 2 THE MOST STABLE RADICAL IS FORMED PREFERENTIALLY I2 UNREACTIVE NOT APPLICABLE cf MAND MAGNITUDE OF FLUORINATION lemoI CHLORINATION lemoI BROMINATION I lemoI kJImoI CHEM237O Solomons Chapter 1o 9 ed DANDEKAR DO PROBLEMS STEREOCHEMISTRY HYBRIDIZATION AT RADICAL SITE SO GEOMETRY SO STEREOCHEMISTRY OF THE PRODUCT WHAT HAPPENS IN THE PRESENCE OF PEROXIDES THE REACTION OCCURS BY A DIFFERENT MECHANISM I SEE 1 MEN 739 EXAMINE THE REGIOCHEMISTRY IN STEP I STRUCTURE OF THE RADICAL IF Br BONDED WITH THE OTHER CARBON WATION OF MOST STABLE INTERMEDIATE RADICAL CHEM237O Solomons Chapter 10 9 ed DANDEKAR MARKOVNIKOV ADDITION m REACTIONS HI ADDS FIRST I ANTIMARKOVNIKOV ADDITION RADICAL REACTIONS Bd ADDS FIRST BOTH OCCUR VIA FORMATION OF MOST STABLE INTERMEDIATE v 41 T r V SECTION 1010 REST OF THE CHAPTER m OF SECTION 105 AB m STRONGLY RECOMMEND THAT YOU GO THROUGH IT CAREFULLY YOU WILL GET A BETTER UNDERSTANDING OF THE REASONS FOR THE DIFFERENCES IN STABILITIES amp REACTIVITIES CHEM 2370002 Dr Sushama A Dandekar SPRING 2009 Lecture M W F 1100 1150 am Room 109 Recitation W 300 350 pm Room 109 OFFICE Chemistry Room 307D PHONE 940 3697090 or 940 5652713 Chemistry Dept Of ce EMAIL sdandekauntedu OFFICE HOURS Mon 200 pm 7 300 pm Tue 1030 am71130 am Other times may be available by appointment TEXTBOOK Required Organic Chemistry 9111 Ed by T W G Solomons and C Fryhle Wiley Optional 1 Study Guide and Solutions Manual for Organic Chemistry 93911 Ed by Solomons and Fryhle 2 A molecular models kit for organic chemistry both optional materials are highlv J A DISABILITIES The Chemistry Department believes in reasonably accommodating individuals with disabilities and complies with the university policy established under section 504 of the Rehabilitation Act of 1973 and the Americans with Disabilities Act 1990 to provide for equal access and opportunity Please communicate with me as to your speci c needs so that appropriate arrangements can be made through the department and or the of ce of Disability Accommodation ODA Room 318A Union 5654323 ATTENDANCE Regular attendance at lectures and recitation is reguired and expected However if you are unable to attend due to reasons beyond your control you must inform me as soon as possible If you are absent from three or more classes without an excuse you may be dropped from the class however do not assume that I will do so Regardless of what your past experience might suggest in this course attendance during recitation is NOT optional Also you will be doing yourself great disservice if you do not attend CHEM 2370002 Dr Sushama A Dandekar SPRING 2009 recitation this is the time when we develop complex problemsolving strategies that will enable you to master the material presented during lecture Not surprisingly there is a strong correlation between regular attendance and excellent performance in this course STUDY AIDS Several useful resources are available online follow the faculty link click on my name from the chemistry department website wwwchemuntedu In the classnotes folder there are three major categories of resources lecture notes chapter objectives and old exams I would strongly recommend that you print out the lecture notes and bring them to class so that you can focus on understanding the material The chapter objectives include a checklist of problem solving skills to help provide structure to your study highlighting the concepts that are crucial for mastering the material covered in class Old exams provide sample questions to help you prepare for exams Similarly the molecular model kit and the solutions manual are invaluable tools to help you master the course content The endofchapter questions in your book will challenge you in myriad ways and if you re stumped the solutions manual can be quite a savior Additionally several useful software programs have been installed on CAS computers located in the various CAS labs on campus Chemistry Building GAB Terrill Hall Wooten Hall these contain tutorials practice problems etc for most topics that will be covered in class and I strongly urge you to make use of them extensively throughout the semester Additional support free of charge is available through the Chemistry Resource Center CRC typically staffed by advanced undergraduate andor graduate students ASSIGNMENTSQUIZZES Several assignments will be given both inclass and as homework typically related to the topic under discussion in lecture Some may involve smallgroup activities The assignments are intended to improve your understanding of various organic chemistry related concepts Quizzes which may be given during lecture or recitation periods are intended to help you keep abreast of material covered in class CHEM 2370002 Dr Sushama A Dandekar SPRING 2009 EXAMS You are responsible for learning and understanding the material covered in the course whether or not you attend class You are also responsible for reading the textbook and solving the endof chapter problems many of the questions on exams will be similar to these in your text Some questions may also pertain to material in the text that was not discussed explicitly in class Do NOT ignore the challenge problems do them to grasp many complex concepts in greater depth M unit exams will be given during the semester Typically these will be during the lecture period The lowest of the four exam scores will be dropped when determining the nal grade Tentative Exam Dates Exam 1 January 30th Exam 2 February 20th Exam 3 March 13th Exam 4 April 17th The Final Exam is comprehensive covering material from the entire semester date and time per the university s nal exam schedule M The nal exam signi cantly impacts your grade so do not become complacent Continue to study diligently right till the end GRADING Your semester grade will be determined as follows Unit Exams 45 of nal grade Assignments Quizzes 15 of nal grade Final Exam 40 of nal grade A grading curve may be used at my discretion to achieve a fair distribution of grades Final Grades will be determined from your cumulative in the following way 90100 A 8089 B 7079 C 5467 D I am looking forward to a wonderful and rewarding semester with youl
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