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 II Summer Session II Question 1 2 3 4 5 Section II Value 18 16 12 12 12 70 Section I Raw Total 30 100 Grade Score UTID CH320 328 N Summer Session II XM2 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 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 2 Which of the following is the correct order of decreasing leaving group ability in nucleophilic acyl substitutions better leaving group worse leaving group a Cl CH3O NH2 b Cl NH2 CH3O c CH3O Cl NH2 d NH2 CH3O Cl 1 3 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 4 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 2 5 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 6 What is the major organic product of the following sequence of reactions a b c d 1 2 3 4 3 7 Which of the following has the highest boiling point a butanoic acid b pentanal c hexane d 1 pentanol 8 Which of the following carboxylic acids undergoes the most rapid thermal decarboxylation reaction a b c d 1 2 3 4 9 What is the IUPAC name of the following compound a b c d pentanoyl isopropane isopropyloxybutanal butyl isopropanoate isopropyl pentanoate 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 major organic product of the following sequence of reactions a b c d 1 2 3 4 5 12 What is the product from this reaction sequence a 2 b 4 c 3 d 1 6 13 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 7 14 What is the major organic product obtained from the following reaction Assume there is a dehydration in step 3 a b c d 1 2 3 4 15 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 8 ID A CH320 328 N Answer Section XM2 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 A A C A A A C D B A C B C D PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 1 UTEID CH 320 328 N EXAM 2 PART 2 Free Style Answer Format KEY 70 pts in this section 1 Kinetic vs Thermodynamic Control 2 methylcyclohexanone can be deprotonated to form two different enolates Each of these enolates in turn can undergo an aldol reaction with benzaldehyde in this case Show the products of these two regiochemical pathways below For full credit you must specify which base conditions will lead to the different products 18 pts O CH3 Provide the kinetic base LDA or NaOtBu NaOH or NaOR Provide the thermodynamic base O O CH3 OR O O CH3 CH3 CH3 OR Draw the Kinetic Enolate Draw the Thermodynamic Enolate CHO CHO 1 1 2 H2O O 2 H2O OH OH O CH3 CH3 Ph Ph Draw the Thermodynamic Product Draw the Kinetic Product 9 UTEID CH 320 328 N EXAM 2 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 10 UTEID CH 320 328 N EXAM 2 KEY 3 Texas two step Provide the reagents in square boxes for these synthesis Note that more than one step may be required in the square boxes For example the acid step of a Grignard addition 12 pts 11 UTEID CH 320 328 N EXAM 2 KEY 4 Reactions Provide the product from each reaction Be sure to include any stereo or regiochemistry if necessary If there is no reaction then place NR in the box 12 pts 12 UTEID CH 320 328 N EXAM 2 KEY 5 Reactions Provide the product from each reaction Be sure to include any stereo or regiochemistry if necessary If there is no reaction then place NR in the box 12 pts END OF EXAM SECTION 13