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Organic Chemistry 2

by: Anika Bernier

Organic Chemistry 2 CHM 550

Anika Bernier
GPA 3.53


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Class Notes
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This 44 page Class Notes was uploaded by Anika Bernier on Monday September 28, 2015. The Class Notes belongs to CHM 550 at Kansas State University taught by Staff in Fall. Since its upload, it has received 113 views. For similar materials see /class/214971/chm-550-kansas-state-university in Chemistry at Kansas State University.

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Date Created: 09/28/15
CHM 550 Organic Chemistry II Instructor Prof Ryan J Rafferty Meeting Tuesday amp Thursday 930am 1045am Willard Hall Room 114 KANSAS STATE IVERS UN TV Who is Prof Rafferty BA UNC Chemistry BS UNC Cellular Biology MS UNC Biochemistry PhD Colorado State University Organic Synthesistotal synthesis PostDoc University of Illinois at Urbana Champaign KANSAS STATE UNIVERSITY Synthetic Organic Chemistry Application OMe Me 5 Me M 1g104 Used NSOg 5200 034g Me 9 C39 39VIe O Me MeBr 0M8 Me 39Me AIBI S Heat Me 25g 061g COIOPadOML Iuivu alt CI OH Me 8 Me O quot Oxalic Me Me quot moPBA EtaN gt gt gt quotH DCM H O O M OMe Li NHa acid tBuOH OMe H20 0 OH OH OH 0304 Me weak 8 Me ACId I OH gt 0 H WIth HotBU Ie FaCIaI H H Selective O O 0 Catalyst Me Me Me MeSi39Me OH C39 OTBS c OTBS Me ITSSCII Me Me MgBr Me ml azoe CuBr quotI gt 2 39 gt DCM THF 0 O O 0 Br Br Br Br T Cl Br Mequot EM 3 Me 0 H 0 NaH Me gt gt Pd N THF N N02 NO NHZ H TS N H tBuLi OH then Br 0 Me Me me N N TS Ts COloradoStateuubu quotif Me Me M u e Si i M Me 8 M M8 9 Me in Me OTBS OTBS OTBS CI OTBS M LHMDS Me Me Me quotI 1 Iu TMSC Iquot H gt e H H gt I H H H O O 0 e OTMS OH OHM OTBS 8 Me Me Me quoth gt Me I INC Me N Ts OTMS N H 11 steps 85 yeld OTBS CU OTBS Me MgBr e CUBE THF 0 O OTBS c OTBS OTBS Me MgBr Me Me CuBrz quoth mCPBA Iquot gt 39 THF OH O OTMS O COIOI39adOStaieuhivu if OH OTBS Me M Me Me M gt gt e I OH OTMS Me N TS OTMS N H Me Me Me Me u u Me I OH Me Me Me gt O gt I No Me NC Me Me Me N 3 H H N N H H I BULi Me QBBN the Me HMe Br r Me Me Me gt gt N N M N M H H Me 8 TSMe e Me Me QBBN Me Mg Mg Me I then Me I then Me Br CI Mel Me CHzBrI Me COIOPadO lilxivu alt Synthetic Organic Chemistry Application H H 11 steps 14 steps 13 steps 18 15 13 31 steps 45 steps Prev39ous 09 035 A 18 steps 20 steps 12 17 ColoradoStateUniversity Complexity to Diversity Synthetic Strategy Application of ring distortion to natural products Ring Ring Won Cleavy a CB WM 0 F08 Ring C6D I 89 ILLINOIS 718677 UNIVERSITY OF ILLINOIS AT URBANACHAMPAIGN Complexity to Diversity Synthetic Stragegy Application of ring distortion to natural products Ring MeO C Me a 2 O O Rlng HO M H Ring FUIIOh 2 e Won Me MeVMe Me Me M6 CO2MG O ILLINOIS r 8639 UNIVERSITY OF ILLINOIS AT URBANACHAMPAIGN CtD Measuring Diversity Scaffolds from Abietic Acid Meoch Me g8 O Q AA16 AA17 AA18 AA19 AA20 KILLINOI UNIVERSITY OFILLINOISAT URBANACHAMPAIGN Rafferty R J Et al Angew Chem Int Ed In Press CtD Library Synthesis 21Membered SinglePoint Derivative Library With Katie Maloof Undergraduate 7 UNIVERSITY OFILLINOISAT URBANA CHAMPAIGN Rafferty R J Et al Angew Chem Int Ed In Press C J Lwnnysw ha s ThreePoint Derivative Library Amidation Wittig Esterlflcatlon Olefination Diels Alder Oxidative Cleavage TILLINOI UNIVERSITY OFILLINOISAT URBANACHAMPAIGN Rafferty R J Et al Angew Chem Int Ed In Press ZOltngtltIOltZltmED HltmOZmO gtwmmgtZD mHOZHAAHHW O s r 20 oz HE z o o m E z 20 1 ms 0 J o IQIOm 22 WI 0 22 viz 1 we o 13 0 ms viz o o 12 t N 010 22 no 022 22 0622 I m o 22 0822 1 ms ummmmuult mucsanoUvw 36x um3lt quotEgg 5 B ENXEQEO Complexity to Diversity Cytotoxicity Illustration of Ring Distortion Me 010012 3902 Me Etf N moon Me MSO gt gt CHQCIIZ CH ll 83 h OH 5 2 Meozc Me AA18 r 39050 MM HeLa gt100 HeLa gt100 HeLa gt100 HeLa 194 17 IVIia Paca 672 14 Mia Paca gt100 Mia Paca gt100 Mia Paca gt100 U937 gt100 V U937 gt100 J U937 294 09 U937 gt100 111 cucoh Me quote PYBOP DMSO Q I BUOOH mCPBA CHZCIIQ CH2ch CH262 gt 97 m t H o CHzpcu2 HN j Me HN j Me HN j Me 34 S S quot o O O S HINI Me I I I o I r N r r ICso MM 1 iCso MM 1 ICso MM ICso MM HeLa gt100 HeLa 97 04 HeLa gt100 HeLa gt100 Mia Paca 328 24 Mia Paca gt100 Mia Paca gt100 Mia Paca gt100 U937 gt100 U937 gt100 y U937 gt100 J U937 gt160 2 TILLINOIS 186 UNIVERSITY OF ILLINOIS AT URBANACHAMPAIGN Rafferty Laboratory at Kansas State University ORGANIC SYNTHESIS DRUG DISCOVERY amp SELECTIVE DELIVERY Total Synthesis of natural products Lead compounds identification through Structural remodeling of advanced bio39ogical screening sythetic intermediates Selectlve drug delivery through chemical Directed selective scaffold synthesis mOdi catiOHS and de39iVery Systems MED39C39NAL CHEM39STRY f CHEMICAL iB flOLGYY SAR of identified lead compounds 4 oUtilizing small molecules to probe Cellular questions Enhancement of therapeutic Devempment Of new small molecules that u Iate effectiveness of small molecules cellular pathways 39foir t heraeutic effects KANSAS STATE M UNIVERSITYe Rafferty Laboratory at Kansas State University Total Synthesis Structuraly Remodeling for Library Construction 39 Total Synthesis Campaigns of Biologically Interesting Compounds com gggny Structural Remodeling of Natural Products Material and Complex Intermediates Library Construction Screening Campaigns of Synthesized Compounds Biochemica1 and Molecular Biology o Medicina1 Chemistry Discovery of New Drug Candidates 10 1028 58020 I 7 1041 SYNTHESIS w OF 39 Egt 5 3069 Intermediates COMPLEX Egt i S f 7 quot 1tjj1101 MOLECULES d quotU Myquot rig I 10 ID 1 FITCA m Inductlon of apoptosls or necrosis Rafferty Research Group KANSAS STATE M UNIVERSITY Rafferty Laboratory at Kansas State University 5 l 7 fquot V 39 quot 4 3 was Ifquot 391quot 321quot 55 new agev aw r e ME v I 1 HH r r t it J i 73 WE i all safari 5 all 1r t as It at 39 l t39 L it Wise t 1W ism 33 oat l at 3 iiiquot Ll axis 3 it t gt it e ti I as M lg n 39 tquot l Investigation Enhancement and Therapeutic Synthesis Of Chemical Library Probing Varying Chemophysical Properties via Ring Closing Metathesis DielsAlder amp Peripheral Modi cation reactions Evaluation of Compounds Upon Blood Brain Penetration Naturemws Drug Discovery 2007 a 650651 Library Construction Elaboration of Scaffolds and Evaluation against various diseases 39 INCORPORATION OF RIGIDITY EBBBMIMIC EVALUAIO Donor Well Butter er Non RingClosing Metathesis RingClosing Metathesis I 39 Compound f o JenOH l Cam 2 Membrane gt gt lt I 1 Br 15 15 Recieving Well Butter Me Me Me I gt gt 0 Me MC KANSAS STATE M UNIVERSITYE Rafferty Research Group Rafferty Laboratory at Kansas State University Development of Selective Drug Delivery Systems Tunable 39Targeting Eclete Receptors due to Over l Triggers Expression within Cancers and Acidic Microenvironments Enhancement of Drugs to Reduce OffTarget Side Effects Evaluation of system in vitrovivo El lt cu C q 1 D D 2 E o q lt 3 9 z m Trigger Removal f MICROENVIRONMENT SELECTIVTIY smow 0X010MO Non Cancerous Drug Approved or Enhanced Therapeutic 3977 Cancer0u5 r KANSAS STATE M UNIVERSITYg Who is Prof Rafferty BA UNC Chemistry 85 UNC Cellular Biology MS UNC Biochemistry PhD Colorado State University Organic Synthesistotal synthesis PostDoc University of Illinois at UrbanaChampaign ORGANIC SYNTHESIS Tota synthesis of natural products Structural remodeling of advanced sythetic intermediates Directed selective scaffold synthesis BIOLOGICAL EVALUATION MEDICINAL CHEMISTRY CHEMICAL BIOLOGY SAFl of identified lead compounds ILI t39i II ziing small molecules to probe cellular question39s Enhancement of therapeutic 39Development of new small molecules that modulate effectiveness of small molecules cellular pathWays39 fer therapeutice eats KANSAS STATE UNIVERSITY CHM 550 ORGANIC CHENIISTRY Fall Semester 2014 Instructor Professor Ryan I Rafferty Of ce CBC 429 Phone 785 532 6624 Of ce Hours 7 Monday 900am 7 950am Thursdays 400pm 7 450pm amp y appointment Email rjraffksuedu COURSE MEETINGS Lectures Tuesday and Thursday 930am 7 1045am 114 Willard Hall QuizExam Supplemental Section Wednesdays 730pm 920pm Cardwell 103 Will not meet weekly Will be used for exams quiz 4 and for make up lectures Chemistry 550 is the second semester of an integrated twosemester sequence of organic chemistry It is expected for you to remember and to be able to employ the concepts and reactions from CHM 531 KANSAS STATE UNIVERSITY HEXUACEU eq NaaH KANSAS STATE U N T V IVERSI COURSE OBJECTIVE The course objective is to gain understanding of the fundamental principles of organic chemistry and to apply those principles to solve problems in molecular science The course is organized in the basis of the structures and reactions of the common functional groups of carbon compounds Understanding the material requires learning the vocabulary drawing correct structural representations and reaction pathways Developing the retentive and analytical skills needed to apply the course content on exams and in subsequent work is the focus of our study The material in this course is not conceptually dif cult but there is much to learn and regylar study is the best way to do well Please see Learning Organic Chemistry below We will be studying a broad topic that is relevant to many areas RE UIRED MATERIALS Text Organic Chemistgy Bruice P 7th Ed Pearson Publishers Models The use of molecular models is strongly advised Model sets should be in stock with the text book Models can also be constructed from other materials Example toothpicks for bonds and jelly beans for atoms can provide useful models Course Website For this course access to K State Online Powered by CANVAS is essential and will be used as a distribution point for lecture summaries answers to suggested problems videos announcements and any changes in the schedu e To access go to hgp publiconlinelltsuedu and select Go to Canvas lower right STATE SAS UNIVERSITY GRADlNG Suggested Problems The best way to learn organic chemistry is to practice as much as possible With that in mind there are several problems that I believe are worth your time in practicing These problems will NOT be collected nor gaded They are for your practice only which I highly encourage doing Quizzes There will be at least ve quizzes 25 points each throughout the semester Four of the quizzes will be armounced see course schedule whereas the other one s will be un announced and at my discretion Quizzes account for 100 points in the course so the four announced quizzes makes up those points The unannounced quizzes are your opportunity to earn extra credit in the course this is the ONLY form of extra credit in the course Once a quiz is started by my announcement in lecture any students entering the room after said point will be NOT ALLOWED to take the quiz Exams Three exams will given throughout the semester on Wednesdays at 730 pm in Cardwell 103 100 points each At the end of the semester your lowest exam will be dropped and replaced with the average of your two other exams You must bring your KSU ID or valid Driver s License Passport etc to each exam for identity veri cation Any exam not veri ed will not be graded During exams nothing is allowed to be with you in your assigned seat during the exam Book bags and what not should be left at home or can be left at the front of the room but KSU personel or myself accept NO responsibility for your possessions You may only have penspencils and a molecular modeling kit at your exam area CELL PHONES OR ANY ELECTRONIC DEVICES are not allowed to be on your person during exams otherwise an XF will be given NO EXCEPTIONSI If you leave any possessions at the front of the room and they ring vibrate or cause any disturbance you will be penalized 15 for each occurrence on said examination STATE SAS UNIVERSITY Exam 1 Wednesday September 24 2014 Exam 2 Wednesday October 29 2014 Exam 3 Wednesday November 19 2014 This exam might be moved to December 3rd Final Exam Wednesday location TBA December 17 2014 from 94Oam7 1130am 200 pts THE FINAL EXAM CAN NOT BE DROPPED OR REPLACEDWITH ANOTHER SCORE Course Points Quizzes 100 points 00 points 00 oints Total points for the course600 points There will be no makeup hour exams but you are allowed an unexcused absence THIS MEANS ONE see exam policy above Letter Grades A 1009000 B 89998000 C 7999 7000 D 6999 6000 and anything below 5999 is an F Percentages are rounded to the hundredth of a decimal There are no awarded at Kansas State Universi Regades Do not write on your graded exams for any reason after they are returned Exams may be photocopied before they are rst returned to you Hour exams may be submitted for regrading up until the end of the class period following that in which the graded exam was returned to the class picking up exams after this class DOES NOT allow you extra time for re grade requests The exam must be submitted directly to the instructor and must include a hand signed cover sheet stating which problems you feel were miss graded and af rming that no changes to the exam were made after grading Re grade requests will cause the entire exam to be regarded and the overall score may therefore either increase or decrease A certain number of exams will be xeroxed before they are returned If an exam submitted for regrading is found to have been altered to correct an error for the purpose of getting more credit this will be considered a violation of the KSUHonor Code and will have serious consequences Arithmetic errors will be corrected immediately KANSAS STATE UNIVERSITY COURSE POLICIES Attendance Attendance is NOT taken in lectures but it is expected that you attend each lecture The correlation between students who achieve good grades and class attendance is strong If you miss any lectures you are responsible for all the material covered Do not come to of ce hours and expect me to give you another lecture over the material Chemistry Help Room CBC 212 1 Help is available to all chemistry students in the Chemistry Help Room in CBC 212 There should be support available for CHM 550 Check the schedule on the door for times and availability Students also have access to a computer and a printer in the help room Academic Resource Center Tutoring Services For information on tutoring hours go to hg39QJhousingk stateeduresourcesarc Tutoring Center at Leasure Hall Free tutoring is available to all enrolled KSU students For information contact the tutoring center at 201 Leasure Hall or by phone 785 532 5703 LEARNING ORGANIC CHEMISTRY The best way to establish and test your mastery of the material in this course is by regular study and working practice problems independently without reference to the text or notes The best test of your understanding of the material in this course is your ability to work the problems Lectures will include guidance practice and advice on working problems The examinations will present problems for you to solve in the allotted time Following is A SINGLE strategy for this course As soon as possible after lecture rewrite your notes A useful approach is to read quickly the relevant section of the text to gain fam iari with the content then read a second time to focus on the important points in the content which correspond to the material in the lecture Then review your notes and work the recommended problems The Bruice text was selected in part because of its excellent presentation of problems and material For each topic study problems and the study solutions are presented in the text followed by problems that should be worked and checked with the study guide At the end of each chapter there are problems whose answers appear in the study guide These kinds of problems are recommended and highly rernmmpnrlml in 19 nrnkle cr hPrlan F qr ihr in drmm39nu cmwmrpc arrI nrnvizlina r nrrPr f nnuxrprc in KANSAS STATE UNIVERSITY Statement Regarding Academic Honesty Kansas State University has an Honor System based on personal integrity which is presumed to be suf cient assurance that in academic matters one s work is performed honestly and without unauthorized assistance Undergraduate and graduate students by registration acknowledge the jurisdiction of the Honor System The pong a s of the Honor System apply to all full and part time students enrolled in undergra a courses 0n campus off campus and via distance learning The honor system website can be reached via the following URL wwwk stateeduhonor A component vital to the Honor System is the inclusion of the Honor Pledge which applies to all assignments examinations or other course work undertaken by students The Honor Pledge is implied whether or not it is stated quotOn my honor as a student I have neither given nor received unauthorized aid on this academic workquot A grade of XF can result from a breach of academic honesty The F indicates failure in the course the X indicates the reason is an Honor Pledge violation Statement Regarding Students with Disabilities Students with disabilities who need classroom accommodations access to technology or information about emergency buildingcampus evacuation processes should contact the Student Access Center andor their instructor Services are available to students with a wide range of disabilities including but not limited to physical disabilities medical conditions learning disabilities attention deficit disorder depression and anxiety If you are a student enrolled in campusonljne courses through the Manhattan or Olathe campuses contact the Student Access Center at accesscenterngg stateedu 785 532 6441 for Salina campus contact the Academic and Career Advising Center at acac quotk stateedu 785 826 2649 Once documentation is obtained through the Student Access Center you must give said documentation to the professor no later than 72 hours prior to the assessment Failure to do so could result in accommodations not being provided or allowed KANSAS STATE UNIVERSITY Statement De ning Expectations for Classroom Conduct All student activities in the University including this course are governed by the Student Judicial Conduct Code as outlined in the Student Governing Association By Laws Article VI Section 3 number 2 Students who engage in behavior that disrupts the learning environment may he asked to leave the class This includes cell phones verbal texting etc computers and conversations DISCUSSING GRADES Due to FERPA regulations only students in the course can ask for grade information and furthermore can only be discussed in person Emails regarding grades will not he answered due to the regulations of FERPA for your protection Important Dates Deadline to AddDrop Course is September 15m chop course with 50 cost by September 22 last day to drop the course without a W Withdrawal on transcript is September 291 and last day to drop with a W on your transcript is October 31S ACKNOWLEDGING AND ACCEPTING THIS SYLLABUS Through writing your name on any quiz and exam and turning in it for grading you are agreeing to the policies of this course outlined in this syllabus and any modi cations hereafter will be amended on line NOTE The professor reserves the right to correct or amend this syllabus as deemed necessary KANSAS STATE UNIVERSITY TENTATIVE SCHEDULE subject to changeVie cuntse chpage for any changes chemjsm reductions mgnno hetermycles carbullydmles 1130am Cnmgrehenxive SUBJECT TO DROP Whm malnng any have KANSAS STATE UNIVERSITY matu39ial ANY QUESTIONS KANSAS STATE WW7 97 V0 mai C Q m awm s L gJ 76 M26hc CC10 Vqne 124 a MC cramde 1L QUL mwi haut LC j qFFQK 010 F D OVJDULQLS OVICLZ eranl 0 339519ng Wavyij m J SKEW1Q Dcr i FPFMltL30KL mmt 64 V r S SMQ go green ag H RVcbvvxcxjr lcljFL C o uquot Q 6 9 Amfi e A Q WW Z 5 x 9 w U 4 W g 2 p 1 003th a 3 39 004 gt Oar 0quot 9 2 5F 5P N W 1 7 6 e A a a x F K 1 X Q lt 3 Luck 518 MR EMA 6i 1 00mamp R6 Q M 9 Q wmoxfL i a l GVC 1L 9WD 5 grown3p CMQ 392 es Xi xx WALL Q O 6 Q A Q 1 Q L 63 Kb A 96 bin 32 WQ L52 3 0Q g 3quot P OVCLR LQierLj J a V0 3 Q 0 6 0W6 d 44 MS 6 W19 Qmmcmi W m CVC FL afm L dip CFJ3HL JD cmdxr 33 W K 39L 70m mcLg m L O H O 5 W 1c 9g M 1 23 TL R Q 391 A n1 N H 9 H H JEOMA 10 OT pf await Kb n H 2 OK quotW49 10 3 l 53 599 hejreroe ms a m S P com 4 k QVOM g 9 Spat HP an 304517 avomlxcx 13 OHMquot W Wig 39r l benzen l 22 OH 93 W


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