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 N Exam 3 Question Value Score 1 12 2 12 3 12 4 16 5 23 Section II 75 Section I 75 Raw Total 150 GradeUTID:____________ April 2012Objective Test SectionIdentify 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)1310N_XM3 1. What is the major organic product obtained from the following reaction?a. 1b. 2c. 3d. 4 2. What is the major organic product obtained from the following reaction?a. 1b. 2c. 3d. 4UTID:________ ID: A2 3. What is the major organic product obtained from the following reaction?a. 1b. 2c. 3d. 4 4. What are the relative positions of the substituents in the following structure?a. parab. metac. orthod. anti 5. Which of the following statements is not true about the structure of benzene?a. the carbon-carbon bonds are all the same lengthb. the structure is an average of two resonance contributorsc. the ring of six carbon atoms is planard. the structure rapidly transforms between two resonance contributorsUTID:________ ID: A3 6. Which of the following does not undergo oxidation in the presence of H2CrO4?a. 1b. 2c. 3d. 4 7. What is the reactive intermediate in the reaction of 1,3-butadiene with HBr resulting in 1,2-addition?a. allylic cationb. dienophilec. allylic radicald. cyclic bromonium cation 8. What is the major organic product obtained from the following reaction?a. 1b. 2c. 3d. 4UTID:________ ID: A4 9. Which of the following molecules is the most acidic?a. 1b. 2c. 3d. 4 10. What is the major organic product obtained from the following reaction?a. 1b. 2c. 3d. 4 11. What is the electrophile in the reaction of benzene with a mixture of nitric acid and sulfuric acid?a. NO+b. NO2+c. benzened. HONOUTID:________ ID: A5 12. What is the major organic product obtained from the following reaction?a. 1b. 2c. 3d. 4 13. What is the major organic product obtained from the following reaction?a. 1b. 2c. 3d. 4UTID:________ ID: A6 14. Which of the following heterocycles is not aromatic?a. 1b. 2c. 3d. 4 15. What is the correct assignment of the names of the following substituted benzenes?a. 1 = phenol; 2 = aniline; 3 = anisoleb. 1 = benzaldehyde; 2 = anisole; 3 = toluenec. 1 = anisole; 2 = xylene; 3 = toluened. 1 = anisole; 2 = aniline; 3 = toluene 16. What is the role of FeBr3 in electrophilic aromatic bromination of benzene using Br2?a. nucleophileb. basec. Lewis acidd. electrophile 17. Which of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3?a. benzeneb. bromobenzenec. nitrobenzened. methoxybenzene (anisole)UTID:________ ID: A7 18. Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?a. 3 > 2 > 1b. 2 > 1 > 3c. 1 > 2 > 3d. 2 > 3 > 1 19. Which of the following are conjugated dienes?a. only 1b. only 2c. only 1 and 2d. 1, 2 and 3 20. Which of the following is not one of Hückel's criteria for aromaticity?a. The compound must have a closed loop of six pi electronsb. The compound must be planar or nearly planar so that there is a continuous overlap of p orbitalsc. The compound must have one p-orbital on each atom of a ringd. The compound must be cyclicUTID:________ ID: A8 21. Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?a. 2 > 1 > 3b. 1 > 3 > 2c. 3 > 2 > 1d. 1 > 2 > 3 22. Which of the following ions is aromatic?a. 1b. 2c. 3d. 4 23. Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions?a. Cl, OH, CH3b. Br, OH, COCH3c. CN, NO2, COCH3d. Cl, CH3, CNUTID:________ ID: A9 24. What is the IUPAC name of the following compound?a. 3-methyl-1,4-pentadieneb. 3-methyl-1,5-pentadienec. (R)-3-methyl-1,4-pentadiened. (R)-3-vinyl-1-butene 25. What is the electrophile in the reaction of benzene with tert-butyl chloride and AlCl3?a. benzeneb. Cl+c. (CH3)C+d. CH3+ID: A1310N_XM3Answer SectionMULTIPLE CHOICE 1. B 2. C 3. B 4. B 5. D 6. D 7. A 8. B 9. B 10. A 11. A 12. B 13. D 14. C 15. D 16. C 17. D 18. B 19. C 20. A 21. D 22. B 23. A 24. A 25. CCH 310 N EXAM #3 UTEID 10KEY PART 2: Free Style Answer Format (75 pts in this section) 1) Provide the product(s) for the following reactions. At least one structure must drawn out, but other regioisomers may be indicated by writing: “ o, p or m isomer” (12 pts) OCOCH3OCOCH3HNO3H2SO4NO2+ p isomerOCOCH3Cl+ p isomerOCOCH3SO3H+ p isomerOCOCH3+ p isomerCl2FeCl3SO3H2SO4CH3CH2CH2ClAlCl3CH 310 N EXAM #3