118BWin15Mt2Key - Chemistry 118 B Winter 2015 Second...

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Unformatted text preview: Chemistry 118 B Winter 2015 Second Midterm Fri. February 27*“, 2015 Instructor: Lievens This exam contains seven (7) pages and nine (9) problems. Please make sure that your copy contains all seven pages. If there is a problem, please tell the exam administrator prior to beginning. Please answer all questions. Remember that UCDaVis Code of Academic Conduct applies to this exam and all other graded work in this class. Please no books. notes, calculators, models, or other aids. Name: Q ? Last First MI 1 Student ID. # T.A.f Lab Section: Total 138 - 1. Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistry. If the product is racemic write racemic or draw both isomers. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state “No Reaction”. heat 3/ A A( A) _, )QN/ 0“" /-- NCS ' B) _—,_ L w] ._ (3,,“ M [W Ci 9') HNO3, H2804 , N02. 0 Q ———~ \ Heat a 01 Must SW“J A'““““ /J\ (1 eq) 4, DIP OK' D) —-———)- AICI3(cat) ““r / CN heat E) + [C l \ ——-)~ F3 lp‘il) each Cl2, H2O 2. Reactions: (12 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemisny. If the product is racemic write racemic or draw both isomers. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. 1) 03/0, WC?“ (/Y :1) 2) H202, H20, NaOH Pd(OA ) ( ), R F’ H) \x/Br ___,.C2 cat 3 .,____ \)\ / cl . ' / HC|(1eq) W M L\ Pig eat”) / Cold / G)\// 3. Vocabulary: (16 pts) Fill in the blanks with the appropriate vocabulary word. If two bold words are given circle the correct one. A) In order to be aromatic a molecule must be C3“; lit. , QOYISUffl and pl am a v" and contain “in 4’2 pi electrons. B) Conjugated pi bonds in linear systems are [email protected] less thermodynamically stable than non-conj ugated pi bonds and also tend to be I less kinetically reactive. C) Halogenation of benzene sometimes 1’ never requires a catalyst. D) In an electrocyclic opening of cyclohexadiene with light the reaction proceeds in a disrotatory / it depends manner. E) The pka of an alkyne C-H is about if , while the CH next to an alkene (allylic) is about H O . F) True {@The reformation of the aromatic ring is the rate determining step in electrophilic aromatic substitution. G) A reaction that proceeds through the most stable intermediate is under Kinti‘lg control. This is generally under high I @nergy conditions and @long reaction times, and gives exo product in Diels—Alder reactions. H) With one equivalent of electrophile conjugated alkenes tend to give I diaddition f a mix of mono and di products. lp’r Each 4. Mechanism: (1? pts.). Show detailed reaction mechanisms for the following reaction. Include all relevant resonance structures and the structure of the expected organic and inorganic products. 803, H2804 G heat 0 mm 1 '1 H5 I _ ‘5 a 5 (—3 s?" 4» H5090 \ é— // Q // “- O// \O O O 0 What is the name of this particular reaction? 5 Ul 'povmlW the What is the name of this particular mechanism? Elec H l] c mah'c S'U , /E’A'S 10k. What is the rate determining step? Grimm/1% S03 [:1 "l' 2 bursa. link} ammahé ‘ ‘ . fl . O Benzene 1n thlS reaction acts as a electrophile - nucleophlle. \ ea ch ' 5. Identification: (10 pts). Label each of the given compounds as aromatic, anti- aromatic, or non-aromatic Qflt‘ ho“ aromn\\i non Gromhc o \ — / / I a Q Q VYV h o In a romalic ant} 0WD mallé Y1 o n \pl' Baal/i 6. Synthesis: (14 pts) Show how you would carry out the following synthesis. Include the reagents you would need for each step and the structure of the intermediate products formed in each step. a W \ . gr W02 0H D thA 51 C2) my 050.1 @ 2W30+ ’99:. w H 3 Lindlqcs N ‘3 NH“ 1, (’9 a @2 j, 23 “2.0 . 32%,?“ ® NH3 AM” flesh“ NW 3 an) amuska 0’ Some, cher— process Mfume 7. Reactivity: (17 pts) Consider the reactivity of alkynes with electrophjles. Fill in one product per box A) ’ Br 3 Br Br“ H3 (1 P HBr {XS} / What would you expect with 0n1y1 equvalent of HCI? {circle one) B} c! 1 \/ HCHXS) % + a. all mono addition C‘ Q b. all diaddllion wt :2. a mix of mono and di 0) 3r 3; 3r Br 3» \/ Br2(1eq} W + W m NaBr Rr. 3:» B'- Rr‘ Br- 8. Nomenclature: (8 pts.) Provide the systematic names or structure of each of the following compounds include EIZJ’RIS where relevant. O OH 3‘ Emmobevnzoic. Wild - . A) Mel‘u— W bwmobemm' and Br B) 3-6%}‘1L 3,13Mevufl hflpsfflh" h ll’dl‘Ol so-lw-z- PMWl 4"” “Phdm OCH} C) 4'(3-butynyl)anisole f8 0 1 1 2'5A33M1 4-!— [Q‘Yn-tnqlpwpynbeh'zm D) 6 w '5 1 054mm- w « iSolw‘l‘rlloam/1215’»: ‘ #JMm-nfiimfia' fiBC 0r "‘ 29s eat/La -I P” "W e Isl/“Lhath 9. Spectroscopy: (20 pts.) The unknown compound A (CHI-1:30) gives the following proton and carbon NMR spectra. Significant IR peaks were also observed. 53H afig 200 150 100 50 0 @0450— Bjcz-c. Z a (312014,chch1 -—=> W1®-CH26H;[email protected] 9'43 17 Ph Pop Pieca. I ’95th SN?» grad/LL Coweo’f‘por-hm ML no shvohm conec’f 1M,le Work. ...
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