Questions on Survey of Organic Chemistry - Exam I | CEM 143, Exams of Organic Chemistry

Download Questions on Survey of Organic Chemistry - Exam I | CEM 143 and more Exams Organic Chemistry in PDF only on Docsity! 1 Chemistry 143 Exam #1 October 19, 2012 Name: ______________________ Student Number: ______________________ Section Number: ______________________ TA: ______________________ INSTRUCTIONS: This examination consists of 33 questions on 10 pages. Please make certain that your examination is complete. Write your name, student number, and section number on both the examination and answer sheet. Be certain to bubble in your PID digits on the answer sheet. The absence of any of these identification items will result in the deduction of 2 points from your score. Questions 1-30 are each worth 3 points. Questions 31 and Question 33 are each worth 3 points. Question 32 is worth 4 points. Write your answers to questions 1- 30 on the enclosed answer sheet. Write your answer to Questions 31-33 in the space provided on this examination. When you complete the examination, insert your answer sheet into your examination and then hand both in on the bench in front of the lecture hall in the spot indicated by your section number. 2 Questions 1-3 are to be answered from the following possibilities: 1. Identify the product(s) formed in the following reaction: (Hint: This reaction proceeds via an intermediate carbocation) a. 1 b. 6 c. 1,6 d. 1,3,8,5,10 e. 6,3,8,5,10 f. 1,6,3,8,5,10 g. 3,8,5,10 2. For the reaction given in Question #1, identify the product(s) that is (are) formed with R absolute configuration: a. 1 b. 6 c. 3 d. 8 e. 5 f. 10 g. 3,10 h. 5,8 i. 3,5 j. 8,10 3. For the reaction provided in Question #1, identify the Z-olefin(s) formed in the reaction: a. 1 b. 6 c. 3 d. 8 e. 5 f. 10 g. 3,10 h. 5,8 i. 3,5 j. 8,10 4. Identify the product(s) formed in the following reaction (Hint: This reaction proceeds via SN2 and E2 mechanisms): a. 4 b. 7 c. 4,7 d. 4,3,8,5,10 e. 7,3,8,5,10 f. 4,7,3,8,5,10 g. 3,8,5,10 1 2 C C CH3 H CH2CH2CH3 H 3 C C CH3CH2 H CH2CH3 H 4 C C H CH3 CH2CH2CH3 H 5 C C H CH3CH2 CH2CH3 H 6 8 C OH CH2CH2CH3 CH3CH2 H C H CH2CH2CH3 CH3CH2 HO C OCH2CH3 CH2CH2CH3 CH3CH2 H C H CH2CH2CH3 CH3CH2 (CH3)3CO C CH2CH2CH3 CH3CH2 H OC(CH3)3 C H CH2CH2CH3 CH3CH2 CH3CH2O 7 9 10 C H CH2CH2CH3 CH2 Br H3C H2O ?acetone C H CH2CH2CH3 CH2 Br H3C ?CH3CH2OH CH3CH2O Na 5 Questions 15 – 18 are to be answered from the following possibilities: 15. 16. 17. 18. Questions 19-23 are to be answered from the following possibilities: a. b. c. d. f. g. h. i. e. j. No Reaction Cl H Cl OH OH H H Cl Cl H H ClCl Cl Cl Cl CH3 NO2 NO2 O2N CH3 NO2 NO2 O2N CH3 NO2 NO2 NO2 H OH OH H A B C D E F G H I J H+, H2O 2) H2O2, NaOH 1) BH3 Cl Cl Cl Cl Cl Cl O O H 1) O3 2) Zn, H+KMnO4 O2, heat CH3 HNO3 H2SO4 ?NO2 NO2 HCl ? Cl ? FeCl3Cl2 KMnO4 ? 6 19. 20. 21. 22. 23. Question 24 refers to the following molecules: 24. Identify all of the trans isomers: (a) 1, 8, 2 (b) 1, 8, 9 (c) 7, 4, 5 (d) 1, 8, 3, 6 (e) 2, 4, 5 (f) 3, 6, 9 Br H H Br Br H Br H CH3 H H CH3 HH CH3 HH CH3 H H 9 2 H CH3 H CH3 CH3 H H3C H H CH3 CH3 H 41 6 7 H3C CH2CH3 H H H3C CH2CH3 H H 3 5 8 ? OH HCl ? ? OH ? H H O O CH3 C C H H+ HgSO4 ? 7 Question 25 and Question 26 refer to the following Newman projection formulas: 25. Which Newman projection formula depicts the most stable conformer of bromoethane? (a) 1 (b) 2 (c) 3 (d) 4 (e) 5 (f) 6 26. Which Newman projection formula depicts the following “dash-wedge” structure? (a) 1 (b) 2 (c) 3 (d) 4 (e) 5 (f) 6 Questions 27 refers to the following conformers of t-butylcyclohexane: 27. Identify all of the equatorial hydrogen atoms in the least stable conformer of t- butylcyclohexane: (a) H1, H8, H4 (b) H1, H8, H4, H3, H7, H10 (c) H2, H5, H6, H9, H11 (d) H2, H6, H11 (e) H5, H9 (f) H3, H10, H7 H H H Br HH CH3 H H CH2Br HH H HH Br H H CH3 HH CH2Br H H 2 3 4 5 Br H H CH3 HH 6 CH3 HH Br H H 1 H H H3C H CH2Br H H10 H8 H9 (H3C)3C H1 H7 H6H1 H11 H3 H2 H4 H5 H7 H6 H2 H3 H5 H4 H8 H9 H11 H10 (CH3)3C