chem3B-fall04-mt1-Ellman-soln

chem3B-fall04-mt1-Ellman-soln - Chemistry 3B, Midterm 1...

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Unformatted text preview: Chemistry 3B, Midterm 1 Wednesday, October 20, 2004 Student name: Student signature: Write TA’s full name (section number) or Lecture Only: 1. , Please make sure that the exam has 9 pages including this one. 2. Please write your answers in the spaces provided. 3. Write clearly; illegible or ambiguous answers will be considered incorrect. 4. Only writing implements are allowed (No Calculators). GOOD LUCK! 1. 8 points 2. 30 points 3. 50 points 4. 17 points 5. 10 points 6. 20 points 7. 20 points 8. 25 points Total 180 points MINI-PERIODIC TABLE 1. Provide structures for the following chemical names (8 points) 0H m1 0 N01 p-chlorophenol 3-nitroaniline Hsc/iLH acetaldehyde 4-methylcyclohexanone “3 2. Answer the following questions. Every wrong answer cancels a correct answer (30 points). (a). Rank the bold hydrogens, that in an 1H NMR spectra would be most shielded (smallest ppm) to most deshielded (largest ppm) [1 = most shielded, 5 = most deshielded] (6 points). HiH H3CiH HH: HO <2; @ @ ti @ (b). Rank the compounds according to those that would react most rapidly to least rapidly with C12, 5233 OH N02 FeC13 [1 = most, 5 = least] (6 points). CH3 CH3 CH3 CH3 CH3 @ 6 (c). Circle the compounds that are aromatic (6 points). E H25 [0] .Q. 2 OH OH OH OH (d). Circle the compounds that would oxidize to an aldehyde or ketone with MnOz (6 points). (e). Circle the d1enes that are capable of undergoing a Diels Alder r - -c.- (6 points). 3. For each of the following reactions supply the missing reagents or major organic product in the space provided. If no reaction is expected indicate by NR. (50 points total). \ 1. hv (a) | / 2. HBr B 1. MeMgBr 2. a ueous worku (b) \JK q p 3. H2804, benzene (xs) r: 1. H20, H+, (d) > — < 2. MeOH, H+, sieves Me OMc (f) 1.CyZBH 2.H202,NaOH 3.NaBH4 1. H20 (under thermodynamic control) 2. PCC, H20 (1: g; «MMOYYK? 4. 22 points total. (a) Show an energy level diagram for the cyclopentadienyl anion shown below (5 points). (b) Place the electrons for the anion in the appropriate molecular orbitals. Does the electron placement establish the molecule as aromatic or antiaromatic? Briefly explain (one sentence is all that is necessary) (5 points). all (.6 4m iv» bowl with Wmahg s m mm are VVWKKJ 50 F—u (c) Compound A is greater than ten orders of magnitude more acidic than Compound B. Explain why compound A is so much more acidic [hintz draw the resonance contributors of the conjugate bases of compounds A and B] (7 points). ; gOH E gOH again 3836MB o {'9 6 Hoe? m 4—) ( W 6C0» Wysilw RWan bu! Sidihiiizéi \MWN film’WWil-C 5/3100“ 5. Circle the compound below that upon heating in water more rapidly undergoes an SN] reaction to give an alcohol. Briefly explain why the compound you circled undergoes the more rapid SNl reaction (10 points). 7Br ’QBr l i SitP/i out 3@ M SW4 a) A G)” r ' & J’U‘ RSQWW Sidifliizzai $ Minn) / a), ,\ J _ I‘M) (yam (oggfie 017mm 60711556 DELL! wion may» O 6. Provide the product of the below transformation. Provide a detailed mechanism for the formation of the product (20 points). HOWOH a {2301’ /U\ H+,. sieves 5% (9‘1 5 € "‘ Mfg/WOW ‘; “16;; Ho H 11‘ H . 6% /“ KW <2 <39 X “r v H20 ism/z: ——> Sta/gs +le MM @W/Weedimhvd ' TD \(Se BI 4M BAH g 7. Provide the product of the reaction listed below. Provide the mechanism by which the reaction product is formed (20 points). Me 0 © C|)J\ , A|C|3 Mo 4 o To 9V1on (0/th 0MB WM 0 “(1233417 i0 SWW Q” QADFWIMA WWW) WWW/W, (Whhujrog 8. Provide the most efficient synthesis. You may employ any reagents of your choice. Points will be assigned according to steps listed in the forward synthesis direction (25 points). MJBY W MW Q] (9:; d g”) dad]; 3:? g @ Than ‘41; him“? Mr H \ ...
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This note was uploaded on 07/05/2010 for the course CHEM N/A taught by Professor Head-gordon during the Fall '09 term at Berkeley.

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chem3B-fall04-mt1-Ellman-soln - Chemistry 3B, Midterm 1...

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