sol_07 - CHEM 5.12 Prof. B. Imperiali PROBLEM SET #7 (this...

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Unformatted text preview: CHEM 5.12 Prof. B. Imperiali PROBLEM SET #7 (this really is PS#7 and the last one was actually PS#6!) fine in Friday April 11th at 4 pm 1. (3 points total) a. For the following compounds estimate the pKa of the hydrogen j g g indicated by the arrow and rank the compounds from the MOST acidic to the LEAST acidic. a"; first" fl'iéiaig fi? H [1 O B MOST LEAST ACIDIC % A D aflg ACIDIC b. You need to seiecte a base to deprotonate ethyne. Using the information derived above —What base would you select if you could choose the conjugate base of any of the acidic species shown above? A); 5; A? as V V” g e disemié‘; ggfivfi; w; 1. .c a, ‘W‘ a 2. HWHZO cawa 4. (6 points) Provide a detailed stepwise mechanism to account for the foilowing reactions. 1 C \3: Al lzmchos I U / A b ,. ‘a a . k a CO2“ O a piggy“)? :eciefim» I O m .0“; ‘ gig-gar fivefigg $W§tm§5 a fig“— fl» H H 2.Na0H/HZO2 O 67, E, 7 E “3 y €1me H g R: \945 M g A FEW} % j gggflgfi if} H ~— B-«H «2AA H 3H gag \wfig Mm? A h) K“ /\> I Z H 1‘, 9' i fl g (3:; gigs? my KM M H H D Eh} Kg” :i” gaugsy I m ‘2, Z y£.§fm :3 n/SHL 6 “i” O H 9 ( w ‘ ‘ M H a I O 52“?» Q? a? W“ a R 3. (8 points) Design syntheses of compounds I and ll. The pool of carbon-containing starting materials that you can use are shown in the square brackets. You may use any other common reagents. A clear retrosynthetic analysis will help you plan the synthesis W T“ £97m skin masts; we” (3 Us 0“ Z “3’ (p ‘ W Q:jk%a$\§. HwaacwH sweats?“ My .Wm. a. w “Vi; ii 2 CZ]st gm“ 2 O WW :5 3 Hz“; RWMZ‘MM as; a N“ m; ...
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sol_07 - CHEM 5.12 Prof. B. Imperiali PROBLEM SET #7 (this...

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