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 Make a record of your scores on 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 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 320 328 N Exam I Summer Session II Question 1 2 3 4 5 6 Section II Value 15 16 12 15 6 6 70 Section I Raw Total 30 100 Grade Score UTID Summer Session II CH320 328 N 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 2pts ea 30 pts this section 1 The multiplicity of protons FbG are a pentet b triplet of quartets c sextet d triplet of triplets 2 What is the relationship between the following two structures a b c d tautomers resonance structures constitutional isomers but not tautomers stereoisomers 3 The multiplicity of proton FdG is a pentet b triplet of quintets c triplet of septets d sextet 1 4 What is the major organic product obtained from the following reaction a b c d 3 phenyl 2 butanol 2 phenyl 2 butanol 3 phenylbutanone propiophenone PhCOCH2CH3 5 What is the major organic product obtained from the following reaction a b c d 2 methyl 1 propanol 1 butene 2 methylpropene 2 butene 6 The multiplicity of protons FcG are a triplet of quartets b pentet c sextet d triplet of triplets 2 7 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 8 What is the major organic product obtained from the following sequence of reactions 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 3 10 The multiplicity of protons FcG are a pentet b sextet c triplet of triplets d triplet of quartets 11 What is the correct assignment of the names of the following functional groups a b c d 1 acetal 2 hydrate 3 enol 4 hemiacetal 1 enol 2 hydrate 3 acetal 4 hemiacetal 1 enol 2 hydrate 3 hemiacetal 4 enol 1 hydrate 2 hemiacetal 3 acetal 4 enol 12 Which of the following is the best choice of solvent for the formation of phenyllithium by the reaction of bromobenzene with lithium a ethanol b tetrahydrofuran c water d acetic acid 13 Which of the following alcohols can be prepared from a Grignard reagent and ethylene oxide a b c d only 1 only 1 and 2 only 1 2 and 3 1 2 3 and 4 4 14 Which combination s of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound a b c d only 1 and 2 only 3 and 4 only 2 and 3 only 1 2 and 3 15 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 5 ID A CH320 328 N Answer Section MULTIPLE CHOICE 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS B B C B C B D B void C C D B B D D PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS 2 2 2 2 2 2 2 PTS 2 awarded to all 2 2 2 2 2 2 2 1 UTEID CH 320 328 N EXAM 1 KEY PART 2 Free Style Answer Format 70 pts in this section 1 Reactions Provide the reagents compounds for the following reactions Number the steps if more than one is required 15 pts 6 UTEID CH 320 328 N EXAM 1 KEY 2 Mechanism Provide a mechanism for the following transformation Show all important flows of electrons charges and intermediates Where indicated in the structure n a box draw the intermediates 16 pts 7 UTEID CH 320 328 N EXAM 1 KEY 3 Texas two step Provide the reagents in square boxes for these synthesis Note that a second reagent may be required in the square boxes For example the acid step of a Grignard addition 12 pts 4 Multi step synthesis Provide the reagents for the following conversions 15 pts 8 UTEID CH 320 328 N EXAM 1 KEY 5 Unknown The NMR spectra of an unknown compound are shown below Propose a structure for the unknown in the box and assign the protons to the spectra on the NMR using the a b c labeling 6 pts C6H12O2 6 3 2 1 7peaks Proposed Structure d d O a c O b OR similar labeling 9 UTEID CH 320 328 N EXAM 1 KEY 6 Unknown The NMR spectra of an unknown compound is shown below Propose a structure for the unknown in the box and assign the protons to the spectra on the NMR using the a b c labeling you may use one letter for all the aromatic protons 6 pts C8H10O 3 5 8 2 7 6 5 4 PPM 3 2 END OF EXAM SECTION 10 1 0