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 6 7 Section II Value 18 8 12 14 12 14 12 90 Section I Raw Total 60 150 Grade Score ID A 320N XM1 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 A C E D B B A B A B A C C D D PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 1 UTEID CH 320 N EXAM 1 PART 2 Free Style Answer Format KEY 90 pts in this section 1 Reactions Provide the products required for the following transformations 18 pt NHCH3 Ph Ph CH3 1 CH3NH2 2 H2 Ni CH3 Ph CH3 N2H4 O KOH Heat Zn Hg HCl Ph CH3 1 EtMgBr 2 H3O NaBH4 MeOH 1 LiAlH4 2 H3O OH Ph OH Et Ph CH3 OH Ph CH3 3 pts each box 8 CH3 UTEID CH 320 N EXAM 1 KEY 2 Wittig Reactions Provide a suitable Wittig or stabilized Wittig reagent for the following transformations 8 pts O O CH3 H3C EtO 2P CO2Et EtO2C CH3 CH3 H3C CH3 M UST be the E isomer O Ph3P Ph OR Ph3P Ph Ph 4 pts per reagent 3 Multi step synthesis Provide the products for the following scheme For full credit you must show the correct regiochemistry 12 pts O HOCH2CH2OH H3O Br H O O Br H OH 1 Mg O 2 CH3CH2CH2CHO O H PCC CH2Cl2 O O HCl aq H O O O H 3 pts per box 9 UTEID CH 320 N EXAM 1 KEY 4 Texas two step Provide both the reagents in square boxes and the product rounded box for these synthesis In some of the steps there is more than one correct method Note that a second reagent may be required in the square boxes For example the acid step of a Grignard addition please include it 14 pts 7 pts scheme 2 pts for reagent box must have all steps 3 pts product box 5 Multi step synthesis Provide the products for the following scheme For full credit you must show the correct regiochemistry 12 pts OH O Ph Ph 1 PhMgBr H2SO4 conc 2 H3O 1 BH3 2 H2O2 NaOH Ph Ph Ph Ph H2SO4 conc OH Ph 1 PhMgBr 2 H3O 2 pts each box 10 Ph O H2CrO4 OH UTEID CH 320 N EXAM 1 KEY 6 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 14 pts H2O H3CO H OCH3 loose a proton OH2 H O CH3OH add a proton break a bond H H H3CO H3CO OCH3 break a bond H3CO add a proton CH3OH H OH2 H3CO H2O make a bond OH H H3CO OH 2 pts per step 7 steps 11 loose a proton OH2 OH UTEID CH 320 N EXAM 1 KEY 7 Synthesis Provide the reagents for the following conversions Note that some transformations may require more than one chemical step e g the acid step of a Grignard reaction For full credit you must include and number these steps when necessary 12 pts O Ph3P HBr CH2 CH2 H Br KOtBu CH2I2 HOtBu Cu Zn Br Cannot be OHor MeO H CH2I2 CH3 2CuLi Cu Zn Br CH3 2 pts per box END OF EXAM SECTION 12 CH3