Exam 6 - Summer 11 (Key)

Exam 6 - Summer 11 (Key) - Sixth Hourly Examination...

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Unformatted text preview: Sixth Hourly Examination Chemistry 8-20 August 8, 2011 8:10 — 9:20 am. Name: _K_E2j_—_______h Section TF: Important Notes: 1. This exam consists of 8 problems on 8 pages, plus this cover sheet, and one page for scratch work at the end of the exam. 2. Ali answers must be written in the spaces provided. Do not write anything in red ink. Answers written on the back of a page will not be graded. Anything written on the Scratch page wiil not be graded. 3. You are allowed to use a set of molecular models for this exam. Problem Score 1. l 12 2' ml 12 Total Score: 3. I 14 4. “—‘—"‘"l 14 l 100 5. l 14 6. I 12 7. l 10 8. ‘ l12 1 Name: KE‘j 1. Each of the following transformations can be carried out in three or fewer steps. Fitl in the reagents required for each step. If a step is not needed, piease put an "X" through that step. a} MO QNH )—OE£ O O—{on 2 1—u—W+Nott\13 3' BFOH b) 1. 1w . __._—_.___,. 2X (11:) 3-X H H _ c) NH2 2. NEb 3' Hz. 'Pé/Q W2C / 1' \=\CD..E:I-, A COzEt d) C o \ 2- “REA ""‘CozEt 3. X (+1“) 112 2 Name: [(59 2. Fill in each box with the starting material or single major organic product of the indicated transformation. Be sure to indicate stereochemistry if it is relevant! a) CH 1. TsCl, pyr f N “L —> 2. News 3. H2, PdlC / ' . 1. LDA b) k —————> o 0 2A 0 DH 3. H+ workup {:H ) 1. NHZOH pH 5 NH O hv ————-———> I12 3 Name: KEV! 3. Provide a compiete curved-arrow mechanism for the following multistep transformation. CCE3 & 0:30— 02— N Jim—>- HN 0 ”OH —‘“"—"')\/\0 00:3 W 114 4 Name: [<5 lj 4. Provide a complete curved—arrow mechanism for all steps of the following multistep transformation. identify and classify all pericyclic reactions. For example: "{4s+25], 67:93 thermal, cycloaddi’tion“. O OH 0 D D ——~—l- ——> + / D ”16 W ELRO Ecru. l j) \ 0 D jfiégfib + \ D o‘flH Cwe' 'D w \ I14 5 Name: [<5 ‘9 5‘ Provide a complete curved-arrow mechanism for all steps of the following multistep enzyme-catalyzed transformation, involved in the biosynthesis of vanillin. Structures of necessary cofactors are shown below. EVE)’ H 0 SCoA 0 800A 800A H W 1 H20 CoASH En-‘thj‘ 2 NAD“ +iSCOA OH fiat—H (spam L K2” I suA Etn‘ti’N . H 0 5% Ho “Q: ”1?“: H \ an? BM—iflH ° ' / ‘ (we. 0H | : \| OH 0\ 3cm ‘ fig” F T elm/“Jug, H “t \o 3m 0 . O gig/Km on I© H—soA R OH x Eat: I14 6 Name: K53 6, Provide a complete synthesis of the following desired product, starting from benzene. You may use any inorganic reagents, and any organic reagents with three or fewer carbons. You do not need to show any mechanisms. The best answer will require eight or fewer total steps. Starting Material: :N03 ”0'“ 316:5) 3“ N02. 15F B (— it; @124 e M”)? NHL U ”33% Jew g” “game gen EFL (XS [y \ QM 1% ? Egg ' , . 3,. life/c. (3r 0 /u\ I NRBHscjt-l Br NJ\ Br Desired Product I12 7 Name: K1331 7. Provide a complete synthesis of the foliowing desired product. You may use any inorganic reagents, and any organic reagents with six or fewer carbons. You do not need to show any mechanisms. You may ignore stereochemistry. The correct answer will require three or fewer total steps. Starting Material: any organic reagents ‘with six or fewer carbons —-—=—-~—-—a was 1. WHEN“ 2. it“ "Jim 0H NEtz Desired Product I10 8 Name: [<53 8. Provide a complete synthesis of the following desired product from benzene. You may use any inorganic reagents, and any organic compounds with five or fewer carbons. You do not need to show any mechanisms. The correct answer will require seven or fewer total steps. Starting Material: Ea. Esp @139 PLUS any organic compounds PI with five or fewer carbons (Li1 {mag Desired Product I12 ...
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