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 320 N Exam I Question 1 2 3 4 5 Section II Value 20 10 18 15 12 75 Section I Raw Total 75 150 Grade Score UTID February 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 XM1 1 The other product from the acid hydrolysis of this imine is a 3 b 4 c 1 d 2 2 Which of the following molecules are deprotonated by ethylmagnesium bromide a propyne CH3C CH b phenol PhOH c dimethylamine CH3 2NH d all of these 1 UTID ID A 3 What is the IUPAC name of the following compound a b c d 3 methyl 3 phenylpropanol 3 phenylbutanoic acid 3 phenyl 1 butanone 3 phenylbutanal 4 The proper reagent s for the following conversion are a PhOH acid b ArOH acid c 1 LiAlH4 2 water d 1 PhMgBr 2 water 5 What is the correct assignment of the names of the following functional groups a b c d 1 oxime 2 imine 3 amine 4 hydrazone 1 imine 2 amine 3 hydrazone 4 oxime 1 imine 2 hydrazone 3 oxime 4 amine 1 hydrazone 2 amine 3 imine 4 oxime 2 UTID ID A 6 What is the major organic product obtained from the following reaction a c b d 7 The structure of the intermediate in the box is a c b d 8 Which of the following compounds is the strongest base a NaOH b CH3OH c CH3Li d NH3 3 UTID ID A 9 What is the major organic product obtained from the following sequence of reactions a b c d 1 2 3 4 10 What is the product of hydrazine and 2 butanone a 2 b 3 c 1 d 4 11 What is the result of the following reaction a formation of a hemiacetal b racemization c formation of a hydrate d No change no reaction 4 UTID ID A 12 What is the IUPAC name of the following compound a b c d 4 phenyl 3 hexanone 1 methyl 1 phenyl 2 butanone 1 2 diethyl 2 phenylethanal 3 phenyl 4 hexanone 13 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 14 The product from the following sequence of reations is a c b d 5 UTID ID A 15 Which of the following alcohols can be prepared from a Grignard reagent and ethylene oxide a b c d only 1 and 2 only 1 and 4 only 1 2 and 3 only 2 and 4 16 What is the major organic product obtained from the following reaction a c b d 17 Which of the following has the highest Keq for enolization a b c d 1 2 3 4 6 UTID ID A 18 The product from this sequence of reactions is a 4 b 3 c 1 d 2 19 What is the product from the following sequence of reactions a c b d 7 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 product of methylamine and acetophenone a 2 b 4 c 3 d 1 22 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 8 UTID ID A 23 What is the major product from the following sequence a c b d 24 The product of this acid catalyzed reaction is a 4 b 2 c 1 d 3 25 Which of the following bonds has the most ionic character a C Al b C Mg c C Hg d C Zn 9 ID A 320N XM1 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 A D D D D D D C B C B A C A D D C B D A A B C D B PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 1 UTEID CH 320 N EXAM 1 KEY PART 2 Free Style Answer Format 75 pts in this section 1 Reactions Fill in the grid below Assume that there is a second hydrolysis step to give the final product Include any region or stereochemistry in the products E G in the first box draw the product from phenylmagnesium bromide and propionaldehyde after the acid step 10 UTEID CH 320 N EXAM 1 KEY 2 Mechanism Provide a mechanism for the following transformation Show all important flows of electrons …