ORGANIC CHEMISTRY I (2301) 9:30 10:20 am, July 21, Exam 3. Form A

Transcription

1 NAME ID # RGANI EMISTRY I (301) 9:30 10:0 am, July 1, 011 Exam 3 Form A If you want to pick this exam up on Tuesday in class (in public), please check the box on the right: If you do not check the box, I will not bring your exam to class on Tuesday, and you will need to pick up your exam in private from hemistry department staff in 115 Smith beginning Tuesday, July 6 th. Exams that are not picked up within two weeks will be disposed of. A periodic table and a chart of reaction conditions are attached to the back of this exam as aids. therwise, you are not permitted to use any other materials (including notes, books, or electronic devices of any kind). Right now, write your name at the top of this page, and fill in the bubbles on the multiple-choice answer sheet for your name and your 7-digit student ID number (in columns 1-7 of the Identification Number section, as shown at right). When the exam begins, also write your name at the top of page 5. You may use pen or pencil. owever, re-grades will be considered only for exams completed in pen. Please write your answers in the bubble sheet for the multiple choice portion of the exam, and in the boxes/spaces provided for the written portion. If your answer is not in the appropriate space in the written portion (say, for example, it s on the back of the page), draw us an arrow and/or note telling us where to look. 1

2 Multiple-hoice Problems Please answer these problems on the bubble sheet. ( pts each) Each of the reactions below is drawn with two possible products, marked (a) and (b). If one of the two products predominates, answer with the letter corresponding to the correct product. If the two products are produced equally, answer (c) BT. If neither product would result from the reaction, answer (d) NEITER Na, N 3 BT NEITER. 1. NaN N N 3 BT NEITER 3. a. b. 1. B 3 TF., BT NEITER BT 3 NEITER

3 KMn, p BT 3 3 NEITER 6. 3 (excess) a. b. 3 3 BT NEITER 7. Pt/ (D = deuterium, heavy isotope of hydrogen) a. b. D 3 D 3 BT NEITER 8. h BT NEITER 3

4 ( pts each) Each of the reactions below is drawn with two possible reaction conditions. If only one of the two reaction conditions would generate the given molecule as the major product, answer with the corresponding letter. If both sets of conditions would accomplish the reaction, answer (c) BT. If neither set of reaction conditions would succeed, answer (d) NEITER Na B BT gs S NEITER mpba KMn / - 3 BT NEITER KMn K, 3,. 3 + BT NEITER (3 pts each) The chemical structure of isopentane shown on the right has three - bonds labeled. 1. Which of the three bonds has the smallest bond dissociation energy (BDE)? 13. Which - would be most likely replaced by a -l in a radical chlorination with l and UV light? 3 a 3 b c

5 NAME Scoring: 1. / / / 15 Total Score: / (0 pts) For each of the reactions shown below, draw a mechanism that explains how the product is generated from the starting material. In your answer, make sure that you: Draw each step of the mechanism separately; Use electron pushing to show where the electrons in each step go; Illustrate stereochemistry where appropriate; Use only the molecules that you are given; do not invoke reactants or solvents that aren t in the problem Mechanism: 5

6 3 l l 3 l l + 3 l 3 l Mechanism: 15. (15 pts) Draw the missing reactant or product in the empty boxes. For products, give the predominant, most favored product. Illustrate stereochemistry in your answer where appropriate. For reactions that yield multiple enantiomers, draw only one enantiomer in the box, and include the note + enantiomer. N 3 (NBS) 3 + trace R l (mpba) 3 3 an alkene 6

7 1. 3. ( 3 ) S 16. (15 pts) For each set of starting materials and products shown below, propose a multistep synthesis. In addition to the molecules shown, you can use any reagents and reactions we ve learned about in class. You might discover multiple answers to this problem; draw only your best (one) synthetic route. Feel free to draw an incomplete route we will give you partial credit where we can. and 7

8 Exam 3 hart of Reaction onditions Reactions to consider from h. 6-7 (Exam ): Acid-Base, S N, S N 1, E, E1 l or, h (benzoyl peroxide) S 1. g(ac) or R. NaB N (NBS) h or AIBN or R 1. B 3 TF., - l mpba Pt/ (g) NaN Pd, BaS (g) N (quinoline) ( 3 ) S Na N 3 gs S 1. (mpba) B KMn, p 7 ( Sia B )., Na 1. KMn K,. 3 + KMn (cold, dilute),

9 Gold Periodic Table of the Elements hemistry Reference Sheet alifornia Standards Test 1 1 1A 1 ydrogen Li Lithium 6.9 Na 11 Sodium K Potassium Rb Rubidium 85.7 A 10 Rf Rutherfordium (61) Mo Molybdenum Atomic number Na Element symbol Sodium Element name.99 Average atomic mass* s 55 esium Fr Francium (3) Be Beryllium 9.01 Mg 1 Magnesium.31 0 a alcium Sr Strontium 87.6 Ba 56 Barium Ra Radium (6) 3 3B 1 Sc Scandium Y Yttrium La 57 Lanthanum Ac Actinium (7) B Ti Titanium Zr Zirconium f afnium B 3 V Vanadium Nb Niobium 9.91 Ta 73 Tantalum Db Dubnium (6) 6 6B r hromium B 3 Tc Technetium (98) W 7 Re 75 Rhenium Tungsten Sg Seaborgium (66) 5 Mn Manganese Bh Bohrium (6) Key 8 6 Fe Iron Ru Ruthenium s 76 smium s assium (69) 9 8B 7 o obalt Rh Rhodium Ir Iridium Mt Meitnerium (68) 10 8 Ni Nickel Pd Palladium Pt Platinum B 9 u opper Ag Silver Au 79 1 B 30 Zn Zinc d admium 11.1 g 80 Mercury A Boron A B 5 arbon Al Aluminum Ga Gallium In Indium Tl Thallium Ge Germanium A 6 Nitrogen Si Silicon Sn Tin Pb 8 Lead A N 7 xygen P Phosphorus As Arsenic Sb Antimony Bi Bismuth A 8 Fluorine S Sulfur Se Selenium Te Tellurium Po 8 Polonium (09) 18 8A e elium F 9 Ne Neon l hlorine omine I Iodine At Astatine (10) 18 Ar Argon Kr Krypton Xe Xenon Rn 86 Radon () * If this number is in parentheses, then it refers to the atomic mass of the most stable isotope. e 58 erium 10.1 Th 90 Thorium Pr Praseodymium Pa 91 Protactinium 31.0 Nd 60 Neodymium 1. 9 U Uranium Pm 61 Promethium (15) Np 93 Neptunium (37) Sm 6 Samarium Pu 9 Plutonium () Eu 63 Europium Am 95 Americium (3) Gd 6 Gadolinium m 96 urium (7) Tb 65 Terbium Bk 97 Berkelium (7) Dy 66 Dysprosium f alifornium (51) o 67 olmium Es 99 Einsteinium (5) 68 Er Erbium Fm 100 Fermium (57) Tm 69 Thulium Md Mendelevium (58) Yb 70 Ytterbium No Nobelium (59) Lu 71 Lutetium Lr Lawrencium (6) opyright 008 alifornia Department of Education