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NAME: FIRST LAST 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 Universitys General Information catalog outlines this universitys 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 I MWF 8AM Question 1 2 3 4 5 6 Section II Value 15 16 12 12 10 10 75 Section I Raw Total 75 150 Grade Score UTID: ________________________ February 2011 CH310N-Exam I Version 2 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. Which C8H10 compound gives the following 1H NMR spectrum? a. b. c. d. 1 2 3 4 2. Which of the protons in the following molecule appear furthest downfield in the 1H NMR spectrum? a. b. c. d. i ii iii iv 1 3. What is the major organic product obtained from the following reaction? a. b. c. d. 1 2 3 4 4. Which of the protons in the following molecule appear furthest downfield in the 1H NMR spectrum? a. b. c. d. i ii iii iv 5. Which feature in the 1H NMR spectrum provides information about the number of types of different protons in a compound? a. chemical shift b. number of signals c. integral d. splitting 6. What is the relationship between the following two structures? a. b. c. d. resonance structures stereoisomers constitutional isomers, but not tautomers tautomers 7. Which of the following bonds undergoes stretching at the highest frequency? a. CH b. CC c. OH d. C=O 2 8. Which of the following bonds (circled) gives a very weak or no stretching absorption in the infrared spectrum? a. b. c. d. 1 2 3 4 9. Which of the following alcohols can be prepared from a Grignard reagent and ethylene oxide? a. b. c. d. only 1 only 1 and 2 only 1, 2 and 3 1, 2, 3 and 4 10. Which of the protons in the following molecule appear at the highest -value in the 1H NMR spectrum? a. b. c. d. i ii iii iv 11. Which of the following compounds is the strongest base? a. CH3CH2OH b. CH3CH3 c. CH3CH2OMgBr d. CH3CH2MgBr 3 12. What is the major organic product obtained from the following reaction? a. b. c. d. 1 2 3 4 13. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by reaction of the Wittig reagent derived from the alkyl bromide with the carbonyl compound? a. b. c. d. only 1 and 2 only 2 and 4 only 2 and 3 only 1, 2 and 3 4 14. Which C6H12O2 compound gives the following 1H NMR spectrum? a. b. c. d. 1 2 3 4 15. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound? a. b. c. d. only 3 only 1 only 1 and 3 only 2 and 4 5 16. What is the major organic product obtained from the following reaction? a. b. c. d. 1 2 3 4 17. What is the major organic product obtained from the following sequence of reactions? a. b. c. d. 2-methylbutane 3-methyl-1-butanol 3-methyl-2-butanol 3-methyl-2-butene 18. Which feature in the 1H NMR spectrum provides information about the electronic environment of the protons in a compound? a. chemical shift b. splitting c. number of signals d. integral 19. Which of the following functional groups is likely to be present in a molecule that has peaks in the infrared spectrum at 3200-3650 cm1 (strong), but does not have peaks at 1630-1820 or 1000-1250 cm 1 a. ether b. ester c. aldehyde or ketone d. alcohol 6 20. Which C8H10 compound gives the following 1H NMR spectrum? a. b. c. d. 1 2 3 4 21. What is the major organic product obtained from the following reaction? a. b. c. d. 4-methyl-1-pentene 2-methypentane (E) 4-methyl-2-pentene 4-methyl-2-pentanol 7 22. What is the major organic product obtained from the following sequence of reactions? a. b. c. d. 1 2 3 4 23. Which of the following laws relates the frequency of a stretching vibration to the masses and spring constant of a simple harmonic oscillator? a. Barrie's law b. Pan's law c. Peter's law d. Hooke's law 24. Which feature in the 1H NMR spectrum provides information about the number of neighboring protons of each proton in the compound? a. number of signals b. multiplicity c. chemical shift d. integral 25. What reactive intermediates are involved in the following reaction? a. b. c. d. the trichloromethyl anion (Cl3C: ) and dichlorocarbene (Cl2C:) the cyclic chloronium ion derived from cyclohexene the trichloromethyl cation (Cl3C+) the cyclohexyl carbocation 8 ID: A CH310N-Exam I version 2 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: Register to View AnswerD C C B A C A B D D B B B B A A A D C D A D B A 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 N EXAM #1 KEY V 3 PART 2: Free Style Answer Format (75 pts in this section) 1) Reactions: Provide the reagents for the following reactions. Note that more than one step may be required. (3 pts ea) 10 UTEID CH 310 N EXAM #1 KEY V 3 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. 11 UTEID CH 310 N EXAM #1 KEY V 3 3) Texas two-step: Provide both the reagents (in square boxes) and the product (rounded box) for these synthesis. (Note, that a second reagent may be required in the square boxes. For example, the acid step of a Grignard addition.) (12 pts): 4) Multi-step synthesis: Provide the reagents for the following conversions. (12 pts) OH Ph CH3 Br2 1) Mg CH2Br heat or h Ph C H2 2) CH3CHO 3) H3O+ CH3 H2CrO4 HN C H2 N CH3NH2 H2; Ni Ph CH3 O CH3 CH3 or NaBH3CN Ph C H2 Ph C H2 CH3 12 CH3 UTEID CH 310 N EXAM #1 KEY V 3 5) Unknowns: The spectra of an unknown compound are shown below. Interpret & summarize the key features of each spectrum (in the space provided) and propose a structure. (10 pts for unknown & interpretation) Unknown 1 C6H12O2 1 MW 116 H NMR- (Integers indicate relative integration of protons) IR: CH stretch, aliphatic <3000 cm-1; C=O, 1740 cm-1; CO 1050cm-1 1 HNMR: 3.68, s, 3H; 2.39, multiplet, 1H; 2.21, d, 2H; 0.91, d, 6H Proposed Structure: 13 UTEID CH 310 N EXAM #1 KEY V 3 6) Unknown: The spectra of an unknown compound are shown below. Interpret & summarize the key features of each spectrum (in the space provided) and propose a structure. (10 pts for unknown & interpretation) Unknown 2 C5H11Br 1 MW 150 H NMR- (Integers indicate relative integration of protons) IR: Aliphatic CH stretches < 3000 cm-1 1 HNMR: 3.42, pentet, 1H; 1.79, multiplet or (d of q), 4 H; 1.05, t, 6H Proposed Structure: Br H END OF EXAM SECTION 14 ... View Full Document

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