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 320 N Exam 3 Question 1 2 3 4 5 6 Section II Value 24 12 9 16 8 6 75 Section I Raw Total 75 150 Grade Score UTID April 2013 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 320N XM3 1 What is the IUPAC name of the following compound a b c d 2 4 dibromohydroxybenzene 4 6 dibromophenol 2 4 dibromophenol 2 4 dibromotoluene 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 Which of the following does not undergo oxidation in the presence of H 2CrO4 a b c d 1 2 3 4 4 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 3 2 1 2 3 5 Which of the following statements is not true about the structure of benzene a the structure rapidly transforms between two resonance contributors b the ring of six carbon atoms is planar c the structure is an average of two resonance contributors d the carbon carbon bonds are all the same length 2 UTID ID A 6 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 7 What is are the major organic product s formed in the following reaction Note reaction temperature is 15o C a b c d only 1 only 2 only 1 and 3 only 2 and 4 3 UTID ID A 8 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 9 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 10 What is the correct assignment of the names of the following substituted benzenes a b c d 1 anisole 2 aniline 3 toluene 1 benzaldehyde 2 anisole 3 toluene 1 phenol 2 aniline 3 anisole 1 anisole 2 xylene 3 toluene 4 UTID ID A 11 What is the product from this reaction sequence a 2 b 1 c 4 d 3 12 Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions a Cl NH2 CH3 b Cl CN NO2 c CH3 OCH3 COCH3 d CH3 NH2 OCH3 5 UTID ID A 13 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 14 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 6 UTID ID A 15 What is the product of this reaction a 3 b 1 c 4 d 2 16 Which of the following are valid resonance structures of the electophile involved in Friedel Crafts acylation of benzene upon treatment with CH 3COCl and AlCl3 a b c d 1 2 3 4 17 Which of the following heterocycles is not aromatic a b c d 1 2 3 4 7 UTID ID A 18 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 19 What is the product from this reaction sequence a 1 b 4 c 3 d 2 8 UTID ID A 20 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 21 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 9 UTID ID A 22 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 3 2 1 1 3 2 23 What is are the major organic product s formed in the following reaction Note reaction temperature is 55o C a b c d only 1 only 2 only 1 and 3 only 2 and 4 24 What is the role of AlCl3 in Friedel Crafts acylations using acid chlorides a base b nucleophile c Lewis acid d electrophile 25 Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions a CH3 OCH3 COCH3 b Cl NH2 CH3 c Cl CN NO2 d CH3 NH2 OCH3 10 ID A 320N 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 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 C B D D A B B D B A D B B C C A C C A B C B A C D PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS …