LAST NAME FIRST NAME UTEID Instructions This exam will be closed book No notes books calculators or molecular models will be allowed The exam will be comprised of two distinct parts Part I will consist of a series of multiple choice questions Your answers to these questions must be submitted on a Scantron bubble sheet The answer sheet will be provided for you but you will need your own 2 pencil s Only answers marked on the bubble sheet will be graded Answers to Part I questions marked on the exam itself cannot not be graded No re grades will be possible on Part I of the exam Part II consists of questions for which you will need to write out your answers using structures and or words This part of the exam will be hand graded Answers for the Part II questions that are written in pencil will not be eligible for re grades Answers written in pencil with ink overlay will not be eligible for re grades If you use a pen to answer the Part II questions only blue or black ink is acceptable Answers written in red ink cannot be graded 1 You must have your valid UT ID card or other government issued ID with you You will need to show it to the proctors when you turn in your exam 2 Chapter 4 of the University s General Information catalog outlines this university s policies regarding exams as well as other quizzes administered during the semester Specifically students are expected to remain in the exam room until a test is completed These policies will be strictly enforced with no exceptions You may not leave the room for any reason until you are ready to turn in your exam If you wish to leave the room you will need to turn in your exam to the proctors and you will not be allowed to return Please plan accordingly by using the rest room before the exam starts CH 318 N Exam III Question 1 2 3 4 5 Section II Value 15 8 16 24 12 75 Section I Raw Total 75 150 Grade Score UTID NOV 2009 CH318N Exam III Objective Test Section Identify the choice that best completes the statement or answers the question There is only one correct answer please carefully bubble your choice on the scantron sheet 3pts ea 75 pts this section 1 What is are the major organic product s formed in the following reaction a b c d only 1 only 1 and 3 only 2 and 4 only 1 and 4 2 Which of the following undergoes the most rapid sulfonation upon treatment with fuming sulfuric acid a nitrobenzene b benzene c benzoic acid d benzonitrile 3 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 4 Which of the following undergoes the most rapid bromination upon treatment with Br 2 FeBr3 a benzene b bromobenzene c anisole d nitrobenzene 1 5 Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions a CH3 NH2 OCH3 b CH3 OCH3 COCH3 c Cl NH2 CH3 d Cl CN NO2 6 Which of the following has the compounds shown in the correct order of decreasing acidity i e more acidic less acidic a b c d 1 3 2 2 3 1 1 2 3 3 2 1 7 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 2 8 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 9 Which of the following ions is aromatic a b c d 1 2 3 4 10 What is the best choice of reagent to achieve the following reaction a b c d Br2 CCl4 HBr H2O NaBr Br2 light 3 11 What are the relative positions of the substituents in the following structure a b c d meta para ortho anti 12 What is the reactive intermediate in the reaction of 1 3 butadiene with HBr resulting in 1 2 addition a allylic radical b dienophile c allylic cation d cyclic bromonium cation 13 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 4 14 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 15 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 16 Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions a CH3 OCH3 COCH3 b Cl NH2 CH3 c CH3 NH2 OCH3 d Cl CN NO2 5 17 Which of the following reaction coordinate diagrams explains the formation of different thermodynamic T and kinetic products from the same reactants R a b c d 1 2 3 4 18 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 6 19 What is the electrophile in the reaction of benzene with tert butyl chloride and AlCl 3 a CH3 b CH3 C c benzene d Cl 20 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 21 Which of the following has the compounds shown in the correct order of decreasing acidity i e more acidic less acidic a b c d 1 2 3 2 3 1 1 3 2 3 2 1 7 22 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 23 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 8 24 What is the electrophile in the reaction of benzene with a mixture of nitric acid and sulfuric acid a HONO b benzene c NO2 d NO 25 What is the role of FeBr3 in electrophilic aromatic bromination of benzene using Br 2 a electrophile b base c nucleophile d Lewis acid 9 ID B CH318N Exam III Answer Section MULTIPLE CHOICE 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS D B C C A B C A B D A C B B C D C D B C A B C C D PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 PTS 3 1 UTEID CH 318 N EXAM 3 KEY PART 2 Free Style Answer Format 75 pts in this section 1 Multi step synthesis Provide the products for the multistep synthesis …