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Organic Chemistry

by: Esteban Towne

Organic Chemistry CHEM 2444

Esteban Towne
GPA 3.91

Ronald Wikholm

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Ronald Wikholm
Class Notes
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This 9 page Class Notes was uploaded by Esteban Towne on Thursday September 17, 2015. The Class Notes belongs to CHEM 2444 at University of Connecticut taught by Ronald Wikholm in Fall. Since its upload, it has received 25 views. For similar materials see /class/205913/chem-2444-university-of-connecticut in Chemistry at University of Connecticut.


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Date Created: 09/17/15
ii 31 Chem 2444 Wikholm Exam No 1 Feb 18 2010 Nam KE Please print your name at the top of the back of the back page of the exam 16O points Supply the reactants reaction conditions or products as appropriate for the following reactions paying particular attention to stereochemistry Wherever pertinent Note that more than one step may be required Make no changes to the given conditions 4 WOH if 4 o 2 W Wz AV b zit31 d I gt I O 3 Mggk e q KI 0 M I W 43 y Arr 0 19quot CGH5 Cb f 39 1 BZHG d Egt 2 H202HO39 b b5WZ 44 M e AIC13 CHZCCl g o Brz f K LE 39quot Chem 2444 Exam 1 Spring 2010 page 2 of 5 pages J A HBChCH aqHZSO4A DOLH 6 o i 300 1 AICI3 HO O 2 H30 0amp0 0 C quot3 97 0 O a 9 39 wawade Bf J G HMS NBS 0l 8 2 Br J Fe ROOR A 9ng Br 39539 M A m ia 5M4 Br CH OH 0M5 ay5 1 l My M m 0042 33quot Q 0 MZJL j AICI3 u 4 OH n CHZCHZEHCHg BPS I quot 0 3a 391 Chem 2444 Exam 1 page 3 of 5 pages V 2 4 points What combination of acyl chloride and arene would you choose to prepare the V following compound by FriedelCrafts acylation g QC a C4 36 points a Which one of the following compounds undergoes bromination of its aromatic ring electrophilic aromatic substitution at the fastest rate new on wet on a0 b d b Which one of the above compounds undergoes bromination of its aromatic ring at the slowest rate 39 5i 44 points Show how the following compound can be formed in a DielsAlder reaction Le give the structures of the reactants 56 points A Which would have the smallest heat of hydrogenation MM 4 W as b Q d B VWhich would have the greatest heat of combustion per CH grouplene or WW 18annulene CIRCLE ONE Chem 2444 Exam 1 page 4 of 5 pages 63 points How many benzylic hydrogens are present in the hydrocarbon shown C a 7 8 points Which of the following is aromatic assuming the molecule can adopt a planar conformation Write YES or NO H I11 3 9 EN Q Va 75 Va 21 s 86 points Circle the correct response in each case a Which would be the weaker base W o o or b Which is the strongest acid or t Chem 2444 Exam 1 page 5 of 5 pages 98 points A The following compound has a 1H NMR spectrum that consists of a single peak With the chemical shift indicated Identify the compound C4H302 5 37 D 0 B The following compound has a 1H NMR spectrum that consists of two peaks both singlets having the chemical shift indicated Identify the compound C6H 1004 5 21 and a f H w3wc0swL 0 1 W3 104 points FriedelCrafts alkylation of toluene with two moles of methyl chloride gives mainly 124trimethylbenzene at 20 C and mainly 135 trimethy1benzene at 120 C Give a reasonable explanation for these observations U MfWW WWW W 0 Mp39 7 621 Chem 2444 Organic Chemistry Section 02 Spring 2011 Instructor Ron Wikholm Of ce CHM A212 8604862173 Hours MWF 911 12 TTh 12 other hours by appointment Email ronwikholmuconnedu Texts Carey and Giuliano Organic Chemistry 8th Ed 7 required the 7Lh or 63911 Eds can be used Carey and Atkins Student Solutions Manual strongly recommended Molecular model kit M M Reading Assignment 1 Jan 18 20 Chapt 10 11 2 25 27 Chapt 11 12 3 Feb 1 3 Chapt 12 MinEl Feb 3 4 8 10 Chapt 13 5 15 17 Chapt 13 Exam 1 Feb 17 Ch 10 11 12 6 22 24 Chapt 14 7 Mar 1 3 Chapt 15 16 MinEZ Mar 3 Springbreak 8 15 17 Chapt 16 17 9 22 24 Chapt 19 Exam2 Mar 22 Ch 13 14 15 16 10 29 31 Chapt 20 11 Apr 5 7 Chapt 18 21 1VIinE3 Apr 7 12 12 14 Chapt 21 13 19 21 Chapt 22 Exam3 Apr 19 Ch 17 19 20 18 21 14 May 26 28 Chapt 23 24 Final Exam Thursday May 5 810 am tentative Jan 31 Last day to drop wo quotWquot Mar 28 Last day to drop a course Course website httphuskyctuconnedu Page 2 Problems from each chapter that appear especially pertinent will be pointed out Such problems must be considered minimal and it is suggested that you work as many other problems as necessary for you to feel comfortable with the material The suggested problems will not be collected or graded but I welcome their discussion Online Quizzes will be available on our HuskyCT site for 72 hours after most of the Thursday lectures during weeks where there is no other exam The five highest scores will count as 50 points toward your total Weekly Problem Sessions will be held on alternate WednesdayThursday evenings at 630 PM in a room TBA Exams are scheduled on the dates noted above Mini exams will be given in class and the exact coverage will be stated at the previous lecture The hour exams will be given during the class time in a room to be announced Each exam is worth 100 points 300 possible points The four mini exam scores will be combined to produce a Fourth Exam 100 points The lowest exam grade will be dropped and replaced with the next lowest grade There will be no make up exams an exam missed for any reason will be considered as the quotdroppedquot exam A cumulative Final Exam will be administered during the scheduled Exam block A total from 550 possible points will be calculated counting the hour exams Exam 4 and the final as 100 points or the three highest hour exams Exam 4 and the final as 200 points whichever total is highest The second option will apply only if all three hour exams are taken or an absence is due to a serious documented emergency Grading loo85 A 8475 B 7460 C 5950 D less than 50 F The above guidelines are percentages of total points and are approximate only Grade distributions will be announced after each exam Cheating in any form and at any task will not be tolerated It is assumed that you are familiar with the concept of academic integrity as described in the University s Student Code httpwwwcommunityuconnedustudenticodeiappendixahtml and elaborated at httpsenateuconneduSenMinsenmin20090202pdf Note that the appropriate academic consequence of academic misconduct is a grade of F in the course Academic misconduct includes but is not limited to Providing or receiving assistance on academic work papers projects examinations in a way that was not authorized by the instructor Any attempt to improperly in uence bribery threats any member of the faculty staff or administration of the University in any matter relating to academics or research Plagiarism Doing academic work for another student Presenting the same or substantially the same papers or projects in two or more courses without the explicit permission of the instructors A student who knowingly assists another student in committing an act of academic misconduct shall be equally accountable for the violation and shall be subject to the sanctions and other remedies described in The Student Code Page 3 Disabled students If you qualify for accommodations because of a documented disability please provide me with a letter from the Center for Students with Disabilities as soon as possible so that your needs may be addressed httpwwwcsduconneduindexhtml Discrimination and harassment The University of Connecticut Policies on Discrimination and Harassment apply to all students staff and faculty See wwwodeuconneduPOLICYSThtml Contact the Office of Diversity and Equity httpwwwodeuconneduindexhtml with any questions or to report any difficulties you might encounter Religious observances Please examine the schedule for the semester and your religious obligations and if you see con icts please notify me as soon as possible See University Senate policy httpsenateuconneduSenMinsenmin20090202pdf For con icts with final examinations students should as usual contact the Office of Student Services and Advocacy formerly the Dean of Students Office Final Exams Rescheduling Policy and Procedure The scheduling of Final Exams is done by the university not by your individual Instructor or department Rescheduling is discouraged and requires special permission When students are forced to miss a Final Exam due to illness accident death in the family or other unavoidable reasons they must obtain permission in writing from the Office of Student Services and Advocacy Students should present the Dean39s office with appropriate documentation to support their request After receiving the Dean39s office permission students should present it to their instructor Who will discuss with them the exact time and location of the rescheduled final exam Please notify your Instructor and start the procedure as early in the semester as possible Additional information can be found at httpwwwossauconnedudocsfmalsilistpdf Academic Achievement Center Learn to fine tune your skills and take control over your academic performance Step up your game and get the grades you really want Study Skills Memory Techniques Time Management Note Taking Test Preparation Goal Setting and more httpaacuconnedu Student Support Services Counseling and Mental Health Services wwwcmhsuconnedu Phone 4864705 after hours use 4863427 0 Career Services wwwcareeruconnedu Phone 4863013 Alcohol and Other Drug Services wwwaoduconnedu Phone 4869431 Office of Student Services and Advocacy wwwossauconnedu Phone 4863426 Center for Students with Disabilities wwwcsduconnedu Phone 4862020 voice 4862077 TDD Page 4 Course Objectives Please read carefully This is the second semester of a twosemester science major s sequence studying the subject of organic chemistry We will continue to examine the subject from an operational point of view which requires understanding of the basic concepts You will learn how to look at an organic molecule and examine it for groups of atoms that will allow you to predict the physical properties and likely reactions of that structure You will be able to derive a unique name for the molecule by applying a systematic set of rules You will be able to predict the structure including the location of the atoms relative to each other and areas of concentration of positive and negative charge You will learn many of the wonderfully unique consequences of the threedimensional structure of molecules You will learn many of the experimental techniques that allow us to determine the structure of molecules In all these endeavors the goal will be the application of logical principles to new situations How to succeed in this course Each of you has had experience with the subject of organic chemistry and now is the time to take stock of how successful the experience was This course is organized around the lectures The expected concepts will be described in the lectures There will be references to the text provided for each lecture and the skills expected from each lecture will be stated As soon as possible after the lecture sit down with the PowerPoint handouts and your in class notes and try to write out the important point behind each slide This will insure that you know what concepts were discussed what examples were presented what suggestions were made etc These ruminations will constitute your study notes for the course It is generally necessary to count on studying a minimum of three hours outside of class for each hour of lecture Your criterion for success in the course is straightforward can you do the assigned problems or can t you Stated another way do you understand the concept being explored in the assigned problem When you work a problem it is important to monitor your success if you need help study buddy Solutions Manual instructor other remember to return to this problem and talk your way through it at a later time At the end of each chapter work the SelfTest in the Solutions Manual for additional practice Ninety percent of an exam will come from these two sources the assigned problems and the SelfTests For many of you organic chemistry will be a uniquely satisfying accomplishment along your educational journey In many ways the demands of orgo will be different from many other academic courses Each topic follows from the previous one if the first is not grasped the second will probably not make sense Once a way of reasoning is attained the material makes perfect sense and everything seems logical The goal is to catch on early and maintain the consistency required to master each lecture s material Note for newcomers to Section 2 Welcome Success in orgo II builds on the foundation of orgo I We will be reviewing all of the important concepts from 2443 in the first two weeks of this semester It is very important for you to decide how familiar you are with this material and how much time you must spend in refreshing your memory Please feel free to visit my office hours to discuss strategies for success in this course RW


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