SampleMt2 - Page 1 Chemistry 1 18A Name Second Midterm...

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Unformatted text preview: Page 1 Chemistry 1 18A Name Second Midterm Student ID No. Fall 2002 PROBLEM POINTS November 19, 2002 Please write the name of Vout ’11 A. _————_—.——.J——-- ‘ ,.___ This exam contains 6 pages and 4 problems. When you are told to start, check to see that all the pages are there. If not, ask for help now. No adjustments will be made later. 1. ( 20 pts) Multiple choice. (a) Most stable 3 H3 H(CH3)2 mam “13%chth CH(CH3)2 CH(CH3)2 (b) Most stable H CH CH 3 2 3 2 . CH3CH2 H=CH2 CH3C 2 CH=CH2 CH=CH2 CH=CH2 (c) Best leaving group (pKa of conjugate acid is given) Br" CH3O" 'SH CI‘ (-4.7) (15.5) (7) (-2.2) (d) Best nucleophile in protic solvent H20 H28 NH3 PH3 (e) Best nucleophile (pKa of conjugate acid is given) I? 'OCCH3 'OCH2CF3 ‘OH 'OCHZCH3 (4.7) (12.4) (15.7) (15.9) Page 2 (f) Most reactive in 8N2 displacement C1 O5 G Ow Ox: (g) Most reactive in SNl displacement Cl <36 G Ow m (h) Least reactive in displacement (all mechanisms considered) C1 {>5 G A OW (i) Best 5N2 solvent 9 9 .9 ’ H20 CH3ICOH CH3CN(CH3)2 CH3CNH2 (j) Best SNl solvent CH3OH H20 CH3COH CH3COCH3 Page 3 2. (32 pts) Write the structure of the major organic product(s) of each reaction. Pay attention to stereochemistry! Then in the space at the right, indicate the mechanism (SNl, 8N2, E1 or E2) by which the major product forms. If no reaction occurs, write “NR”. (a) H OH NaI /\/‘< DMSO Mechanism \ l i (C) CL H P-I C1 NaSCH3 ———-—-> acetone (d) 1‘ H NaOCH3 CH3OH CH3OH CH3OH KOC CH /\/\1 ( 3b (CH3)3COH (g) {3 (h) NaOH _._——————> DMF _ [Formula 13 C4HBO] Page 4 3. (30 pts) (a) Even though all four of the compounds below are primary haloalkanes, they react with I‘ in DMSO with different rates. /\/Cl /k/Cl >0“ /\C1 —.—— ————.——————— In the spaces below each structure rank its relative reactivity (1 = fastest to 4 = slowest) among the four. Then, in the space below, hfigflx explain your reasoning. (b) The stereochemical outcome of the reaction below depends on the solvent. H C1 W (5) AA + Na+ "OCCH3 What product(s) would you expect to form if the reaction is carried out in water? What product(s) would you expect to form if the reaction is carried out in acetone CH3COCH3? Page 5 (c) Explain your answers to part (b) above, by illustrating with mechanistic equations. 1‘? CCH3 (d) The two enantiomers of /\/K have distinctly different odors; both H c1 are used as perfume components. Describe a method for converting (S) M i? . H o'CCHg , . . into ~ muggy; also forming the (R) enantiomer. (S)— Hint: your method will require more than one step. Page 6 4. (18 pts) Give a complete, systematic name to each compound below. Indicate in the space at the right whether or not-the molecule is chiral. Chiral or not (C) The molecule in (c) and the molecule in (d) are 4‘ . Be specific in using the proper word to describe the 5339mm! relationship between the two molecules. ...
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