LAST NAME FIRST NAME UTEID COVER PAGE 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 310 N Exam 3 Question 1 2 3 4 5 Section II Value 12 12 12 16 23 75 Section I Raw Total 75 150 Grade Score UTID April 2012 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 310N XM3 1 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 2 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 1 UTID ID A 3 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 4 What are the relative positions of the substituents in the following structure a b c d para meta ortho anti 5 Which of the following statements is not true about the structure of benzene a the carbon carbon bonds are all the same length b the structure is an average of two resonance contributors c the ring of six carbon atoms is planar d the structure rapidly transforms between two resonance contributors 2 UTID ID A 6 Which of the following does not undergo oxidation in the presence of H 2CrO4 a b c d 1 2 3 4 7 What is the reactive intermediate in the reaction of 1 3 butadiene with HBr resulting in 1 2 addition a allylic cation b dienophile c allylic radical d cyclic bromonium cation 8 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 3 UTID ID A 9 Which of the following molecules is the most acidic a b c d 1 2 3 4 10 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 11 What is the electrophile in the reaction of benzene with a mixture of nitric acid and sulfuric acid a NO b NO2 c benzene d HONO 4 UTID ID A 12 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 13 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 5 UTID ID A 14 Which of the following heterocycles is not aromatic a b c d 1 2 3 4 15 What is the correct assignment of the names of the following substituted benzenes a b c d 1 phenol 2 aniline 3 anisole 1 benzaldehyde 2 anisole 3 toluene 1 anisole 2 xylene 3 toluene 1 anisole 2 aniline 3 toluene 16 What is the role of FeBr3 in electrophilic aromatic bromination of benzene using Br 2 a nucleophile b base c Lewis acid d electrophile 17 Which of the following undergoes the most rapid bromination upon treatment with Br 2 FeBr3 a benzene b bromobenzene c nitrobenzene d methoxybenzene anisole 6 UTID ID A 18 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 3 2 1 2 1 3 1 2 3 2 3 1 19 Which of the following are conjugated dienes a b c d only 1 only 2 only 1 and 2 1 2 and 3 20 Which of the following is not one of H ckel s criteria for aromaticity a The compound must have a closed loop of six pi electrons b The compound must be planar or nearly planar so that there is a continuous overlap of p c d orbitals The compound must have one p orbital on each atom of a ring The compound must be cyclic 7 UTID ID A 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 2 1 3 1 3 2 3 2 1 1 2 3 22 Which of the following ions is aromatic a b c d 1 2 3 4 23 Which of the following sets of substituents are all ortho para directing in electrophilic aromatic substitution reactions a Cl OH CH3 b Br OH COCH3 c CN NO2 COCH3 d Cl CH3 CN 8 UTID ID A 24 What is the IUPAC name of the following compound a b c d 3 methyl 1 4 pentadiene 3 methyl 1 5 pentadiene R 3 methyl 1 4 pentadiene R 3 vinyl 1 butene 25 What is the electrophile in the reaction of benzene with tert butyl chloride and AlCl3 a benzene b Cl c CH3 C d CH3 9 ID A 310N XM3 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 B C B B D D A B B A A B D C D C D B C A D B A A C 1 UTEID CH 310 N EXAM 3 PART …