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Answer Key Exam 2

Answer Key Exam 2 - NAME CHEM 354 — Organic Chemistry II...

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Unformatted text preview: NAME: __ CHEM 354 — Organic Chemistry II Exam 2 PERIODIC TABLE OF THE ELEMENTS 1A 8A 1 H 1.008 . 2A 3A 4A 5A 6A 7A 003 3 4 Be 5 B 6 C 7 8 9 10 Li 6.9 9.012 10.81 12.011 N O F Ne 41 14.007 15.999 18.998 20.179 11 Na 12 M ---- 1B 2B 13 Al 14 Si 15 P 16 S 17 Cl 18 22.99g 24.3 26.98 28.08 309732.06 35.45 Ar 0 05 2 6 4 3 39.948 19 K20 Ca 21 Sc 22 T123 V 24 Cr 25 M 26 Fe 27 C028 Ni 29 C1130 Zn 1 G332 Ge 33 As 34 35 36 39.09 40.08 44.95 47.90 50.94 51.99 11 54.9 55.84 58.93 58.70 63.54 65.38 69.72 72.59 74.92 Se Br Kr 8 6 2 6 38 7 3 6 2 78.96 79.904 83.80 37 Rb 38 Sr 39 Y 40 Zr41 Nb 42 M43 T044 Ru45 Rh46 Pd47 Ag48 Cd 49 In 50 51 52 53 54 85.46 87.62 88.90 91.22 92.900 95.9 (98) 101.0 102.9 106.4 107.8 112.4 114.8 Sn Sb Te 1 Xe 8 6 6 4 7 l 7 1 2 118.69 121.75 127.60 126.90 131.30 55 Cs 56 Ba 57# L72 H 73 Ta 74 W75 Re 76 Os 77 Ir 78 Pt 79 Au 8O 81 82 83 84 85 86 132.9 137.3 a 138. 178.4 180.9 183.8 186.2 190.2 192.2 195.0 196.9 Hg T1 Pb Bi Po At Rn 1 3 91 9 5 5 1 2 9 7 200.59 204.37 207.2 200.98 (209) (210) (222) 87 Fr 88 Ra89_ A (223) 226.0c 227. 3 03 58 Ce59 Pr60 Nd 61 62 63 64 65 66 67 68 69 7o 71 140.1 140.9 144.2 Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu 2 1 4 (145) 150.4 151.96 157.25 158.93 1625016493 1672616893 1730417497 90 Th9] Pa 92 U93 Np 94 95 96 97 98 99 100 101 102 103 232.0 231.0 238.0 237.0 Pu Am Cm Bk (:1 Es Fm Md No Lr 4 4 3 5 (244) (243) (247) (247) (251) (252) (257) (258) (259) (260) NAME: Multiple Choice: 3 points each 1. In the 1H NMR , in what region of the spectrum does one typically observe hydrogens bound to the aromatic ring? a. 1.0-1.5 ppm b.2.0-3.0 ppm c. 4.5-5.5 ppm (1. 7.0-8.0 ppm e. 9.0-10.0 ppm (A ¢\ 2. How many distinct trichlorobenzene isomers are possible? c; (‘fi 0 ..\°/'-r_! Cl C: c) Cl a. 2 63) c. 4 d. 5 e. 6 \J—J‘f \K 3. What is the hybridization of the end carbon of allene (1,2-propadiene)? MC 7.; 3 c 9.1 at r a. sp 'p2 c. sp3 (1. p e. none of the above 4. When the relative energies of the s-cis and the s-trans conformers of 1,3-butadiene are compared, one finds a a ,/ a. that the s-cis conformer is lower in energy than the s—trans. " K / 6) that the s-trans conformer is lower in energy than the s—cis. 5 (C ‘. S ngC-WM c. that the two conformers are equal in energy. d. that the s—cz‘s conformer is more stable than the s~trans. 5. Which of the following compounds absorbs the longest wavelength of UV-Visible light? /\‘/ /:| W a. (E)—2-butene b. (Z)-2-butene c. 1,3,4-hexatriene d. 1,3-hexadieneNv @ ,3,5—heptatriene W‘ 6. Absorption of UV-visible energy by a molecule results in a. vibrational transitions ®electronic transitions 0. rotational transitions d. nuclear transitions e. none of the above 7. Which of the following compounds has the highest melting point? a. benzene b. toluene c. o—dichlorobenzene d. m-dichlorobenzene @p—dichlorobenzene 8.Which of the following compounds is the weakest base? EH2 H -. I? <3 i /N N: " | a. U c. L) (1. \0M Cu'.’ J“ W at mm- L NAME: 9. Which of the following is an incorrect description of benzene? a. The CCC bond angles are all equal to 120". \ “YUM b. The molecule is planar. 0“ Wm“ “‘3 Sued; @The molecule is a 6-membered ring which contains alternating double and single bonds. d. The molecule is aromatic. e. The molecule can be drawn as a resonance hybrid of two structures. 10. Which of the following compounds is not aromatic? . @i; :3 (mes-i6 Afiwl'fie L‘ha-lo _ m _ 5 "“ I: " '7: N fi' :1 Nomenclature: Give the name for each of the following chemical structures. Give the structure for each of the following chemical names. Be sure to include stereochemical designations if necessary. 3 points each NH2 CN 0 / 2 _ o.\\ :9 cr¢~§\§.n.Q catechol benzyl alcohol p-isobutylbenzoic acid L) m CW" (—3“ V o\'\ c) \ O W NAME: Predict the Products: Give the major organic products for seven (7) of the nine reactions shown below. Be sure to include stereochernical designations if necessary. Clearly indicate which of the seven (7) reactions you wish to have graded; otherwise I will grade the first seven reactions answered. 5 points each EtOH d‘" Bide A V o ,4 o O O r o 0 U + \ / —’ \ L" \o c. \u” 0 o C0,HC] ‘ (2 L0“ 01- A1C13 ' ‘3 ,orh (CH3)2CHCH2COCI G” -u\3 AlCl 3 NAME: Synthesis: a. Provide a series of synthetic steps by which the compound below can be prepared form benzene. 6 points Norah?» W ——> _,. (J \) \ “Ch-5 4 v / (an hv G ZKUAS) HQ l ‘9 Short Answer: A student was studying terpene synthesis, and she wanted to make the compound shown below. First she converted 3-bromo-6-methylcyclohexene to alcohol A with sulfuric acid and purified one of the components (compound B) from the resulting mixture. Compound B has the correct molecular formula for the desired product. 6 points H2804 heat l compound A compound B 3.. Suggest how 3-bromo-6-methylcyclohexene might be converted to alcohol A. 6, (MB ' \‘t b. The UV spectrum of compound B shows km,“ at 273 nm Is compound B the correct product? If not, suggest a structure for compound B con ‘ - ~ - -‘- UV data. 255 \ 9V; em [’31—- U\ Q firm-Q5 U) IA (2—5wa 1;)”; “1K ‘ 1a 9 ow NAME: Mechanism: Show how benzene is converted to nitrobenzene upon treatment with nitric acid and sulfuric acid. You must use curved—arrow formalism for each step to illustrate formation of this product. 8 points 6; U 69/0 G.) \‘ a L): :C} “‘O'N20 kWh-0H 7 p.313 “‘9 r o-§ GA 230 ‘3 (5 H OE.) 0 +990 0 d 3 "‘ E‘s-o” /\_) "U 9 H/“’ “0‘ 6° \ ' Dd A? \ + e? \/ \l (“J 6 \j“ *4” Pro—i «3 , (J \/ ‘0 WA? Bonus: Write you own question. From your experience with point value on this and previous test, write a 10 point question over material in Chapter 15, Chapter 16, or Chapter 17 that was not covered on this exam. 10 points ...
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