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 2 Question 1 2 3 4 5 Section II Value 12 30 14 9 10 75 Section I Raw Total 75 150 Grade Score UTID March 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 XM2 1 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 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 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 4 What is the best choice of reagent to achieve the following transformation a b c d CH3MgBr CH3Li CH3 2CuLi CH3I 5 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 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 the major organic product obtained from the following reaction a b c d 1 2 3 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 Which of the following is the correct order of decreasing acid strength more acidic less acidic a CH3CH2OH ClCH2COOH BrCH2COOH b CH3COOH ClCH2COOH CH3OH c FCH2COOH CH3COOH F2CHCOOH d FCH2COOH CH3COOH CH3OH 10 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 4 UTID ID A 11 What is the major organic product of the following sequence of reactions a b c d 1 2 3 4 12 What is the IUPAC name of the following compound a b c d trans 3 methylcyclohexanecarboxylic acid trans 4 methylcyclohexanecarboxylic acid cis 4 methylcyclohexanecarboxylic acid cis 3 methylcyclohexanecarboxylic acid 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 major organic product obtained from the following sequence of reactions a b c d 1 2 3 4 16 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 17 Which of the following has the highest boiling point a butanoic acid b pentanal c acetic acid d pentanol 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 major organic product of the following sequence of reactions a b c d 1 2 3 4 8 UTID ID A 20 Which of the following carboxylic acids undergoes the most rapid thermal decarboxylation 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 What is the major organic product of the following sequence of reactions a b c d 1 2 3 4 23 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 10 UTID ID A 24 What is the major organic product obtained from the following sequence of reactions a b c d 1 2 3 4 25 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 11 ID A 320N XM2 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 A B C C A A B D B A C D D A C A C B C B B B A 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 2 PART 2 Free Style Answer Format KEY 75 pts in this section 1 Reactions Provide the reagents for the following reactions This is not a mechanism question simply write the answers in the boxes Note that 2 steps may be necessary 12 pts O Ph O OH O H3O or 1 OH 2 H3O O O O OH OH SOCl2 or SO2Cl2 H3O or 1 OH 2 H3O O O NHCH3 Cl O OCH3 CH3NH2 heat 11 NaOCH3 or CH3OH UTEID CH …