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040220-key - NAME KEV(please PRINT Chemistry 1093 Exam ll...

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Unformatted text preview: NAME: KEV (please PRINT) Chemistry 1093 Exam ll “February 20, 2004 ‘ Q Value Total 35 2. 1x14 14 3. 15+2+10+4 31 80' q? “Sure, we’re dealing with tiny particles, but your formula is just a “E ’ me ~ : r 2 v u 15.. a".ix’"s " : r-r :‘I < :- Score 1. Provide the major organic product(s) from the following transformations. Indicate stereochemistry where appropriate. (a (b) ( (d (e (f) (g) c ) O ). w o; 4 V 9H ) /\g\/\ ) MCHO I // Q/lh dick I CHO 1, LM, WF, 48' 2. 020 1. Pkg—L511)”: 2. NM! , 8'33 3. Lind!” Mum-m I, --—-——-——-—> 2.. HONHZ, rt I. Hui-Q at. h”r 2. LCM, THF, 0' 3. me”; l. x’: Na/tq.NH3 2. 03, 48’ 3. {ones man-4' I. H30‘r 2. NaBHq. aqueovs Naofi n II. Converting compound 1 below totarget ester 2 should be as easy as displacing the bromide with acetate ion (CH3C02'). Unfortunately, you do not have access to this nucleophile and must devise an alternative route not involving acetate (or hydroxide) ion. Thus, using any other reagents, - suggest a short synthesis of 2 from 1. Br Ph reagents ? Ph 0 1 2 I. g ‘ CH3002' f O S 'L‘ I Hg" 7', R603 H " /\/\/\\ —--———-~ h ——--=' ’2 "I, -——-—-.., P}, \\ W I "w P My A III. Treating ketone 3 as indicated below forms new product 4, which upon ozonolysis and workup with dimethyl sulfide leads to new product 5. ~Wo‘lff—Kishner (W-K) reduction of 5 gives hydrocarbon 6. (a) Provide structures-for products 4-6 (in the boxes above). ' . (b) Give the 'name‘ associated with the 3 to 4 conversion. nth , (c) Suggest a mechanism for this'3 to 4 conversion. (d) What are the reagents needed for the Wolff-Kishner reaction (5 to 6)? +9}; in: a m” aim 1;, CC) 0 8' lbs? ,, r 3/:W , f ’0, 0 Jth W "0‘: ° ...
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