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 310/318 M Exam 2 v 1.0 Question 1 2 3 4 5 Section II Value 24 10 20 11 10 75 Section I Raw Total 75 150 Grade Score UTID: ________________________ October 2010 CH310/318M-Exam 2 VERSION 1 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) 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 alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration (treatment with aqueous H2SO4)? a. b. c. d. 1 2 3 4 3. What is the IUPAC name of the following compound? a. b. c. d. (E)-3-methyl-3-pentene (Z)-3-methyl-3-pentene (E)-3-methyl-2-pentene (Z)-3-methyl-2-pentene 1 4. What is the index of hydrogen deficiency of a compound with a molecular formula of C 6H8? a. 0 b. 1 c. 2 d. 3 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 obtained from the following reaction? a. b. c. d. 1 2 3 4 7. What is (are) the major organic product(s) obtained from the following reaction? 1. 2. 3. a. b. c. d. (2R,3R)-dibromobutane (2S,3S)-dibromobutane meso-2,3-dibromobutane only 1 only 2 only 3 only 1 and 2 2 8. What is the major organic product obtained from the following reaction? 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 10. Which atom in the following structure is preferentially protonated by a strong acid? a. b. c. d. i ii iii iv 3 11. What is (are) the major organic product(s) obtained from the following reaction? a. b. c. d. only 1 only 2 only 3 only 2 and 3 12. Which of the following terms describes the role of ethanol in the acid-base reaction shown? a. b. c. d. Brønsted-Lowry acid Brønsted-Lowry base Lewis acid Lewis base 13. What is the correct order of stability of the following carbocations (more stable > less stable)? a. b. c. d. 1>2>3 1>3>2 3>1>2 3>2>1 14. What is the IUPAC name of the following compound? a. b. c. d. 2-methylenepentane 2-methyl-1-pentene 2-vinylpentane 2-propyl-1-propene 4 15. What is the best choice of reagent to perform the following transformation? a. b. c. d. Br2 HBr Br2, H2O N-bromosuccinimide 16. What type of reactive intermediate is formed in the reaction of an alkene with Br2 and water to give a bromohydrin? a. carbocation b. carbanion c. radical d. cyclic bromonium ion 17. Which of the following terms describes the role of ethene in the acid-base reaction shown? a. b. c. d. Brønsted-Lowry acid Brønsted-Lowry base Lewis acid Lewis base 5 18. What is the major organic product obtained from the following reaction? a. b. c. d. 1 2 3 4 19. Which of the following energy diagrams best represents the changes in energy during addition of HBr to an alkene? a. b. c. d. 1 2 3 4 6 20. What is the best choice of reagent(s) to perform the following transformation? a. b. c. d. H2O, H2SO4 Hg(OAc)2 and H2O ; followed by NaBH4 B2H6; followed by H2O2, NaOH OsO4; followed by NaHSO3 21. Which set of curved arrows accounts for the deprotonation of an acid (A-H) by a base (:B)? a. b. c. d. 1 2 3 4 22. What type of carbocation is shown? a. b. c. d. primary secondary tertiary quaternary 23. Which species is the conjugate acid in the following acid-base reaction? a. b. c. d. 1 2 3 4 7 24. Approximately how long is a carbon-carbon triple bond of an alkyne? a. 110 pm b. 121 pm c. 135 pm d. 156 pm 25. What is the major organic product obtained from the following reaction? a. b. c. d. 1 2 3 4 8 ID: A CH310/318M-Exam 2 VERSION 1 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: B B D D B B C D C A A A D B C D B B A C B B D B 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 310/318 M EXAM #2 v 1.0 PART 2: Free Style Answer Format KEY (75 pts in this section) 1) Provide the reagents and steps for each of the following transformations. For credit, your reactions must be stereo and regiospecific when necessary. Note, that there may be more than one method to achieve the product, but you need only provide one. (24 pts) CH3 CH3 Br Br OH H CH3 H Br2; CH2Cl2 1) Hg(OAc)2 2) NaBH4 H OH OR H2SO4 (aq) CH3 Br H HBr but NOT aqueous H CH3 H 1) BH3 2) H2O2; NaOH HCl but NOT aqueous Br2; H2O CH3 CH3 OH H H Br H 6 Cl H UTEID CH 310/318 M EXAM #2 v 1.0 KEY 2) One of the advantages of developing different reagents for organic synthesis, is the ability to control the products. 3,3-dimethyl-1-butene can be converted into 2 different products by the reagents below. Draw the products, and indicate any regiochemistry. (10 pts) 3) 1,3-butadiene will undergo addition reactions with HBr to form 2 products. Follow the instructions for the mechanism and predict the structure of these two products. (Hint: the carbocation is stabilized by resonance.) (20 pts) H H H Br H H H H Form the carbocation Br Br Show the 2 resonance structures H H H H H Br H Br Show the 2products, which result from the attack of Bromide 7 UTEID CH 310/318 M EXAM #2 v 1.0 KEY 4) Mechanism The experimental evidence for the bromonium ion, is the stereochemistry of the products. For the bromination of E-stilbene, show the mechanism and label the stereochemistry of the product. Chiral centers are produced, so assign the R & S designation to the chiral carbons. (11 pts) 8 UTEID CH 310/318 M EXAM #2 v 1.0 KEY 5) Reactions. Provide the products of the following reactions. For full credit, show stereo and regiochemistry where necessary. (10 pts) OH H2C OH 1) OsO4 2) NaHSO3 H CH3 CH3 H2 Pt or Pd or Ni CH2CH3 H END OF EXAM 9 CH2CH3