2006exam2-key - L/e/j Organic Chemistry 345 Name (Please...

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Unformatted text preview: L/e/j Organic Chemistry 345 Name (Please Write Clearly) Spring 2006 Exam 2b Student ID Home Street Name (as in UW Records) Your Seat Number Question Points Grader’s Initials l 2 10 (20 Points each for Questions-1, 2 and 3; 16 Points for Question 4; 4 Points for Questions 5,6,7,8,9,10. Page 7 to be used for Scratch PgZ Organic Chemistry 345 Spring 2006 Exam 2b Name (Please Write Clearly) 1. Give the products of synthesis as isolated after workup. F? ——r- S a) a 1) M )(5/% Y 2) Benzyl Bromide 6+ b) Et _ AN“- PhC=N LiAlH4, Et20 F“ 1 OH O c) Cumene C:- d + JL, Hydroperoxide DiL H2804 - N \ I Me M45 n“ : / \ e) m , H CI' ' _ o f) Malon'ic Acid —'——> Ho/Lk 110° ) ‘3’ g .Acetophenone+ MezNH+ CH2=O HCI i’hMHLz Phthallc Anhydride + Benzylamlne it u- H c) o O . 2 KNH2 Liq NHs i) - Ph-C-CHz-C-CHS II II Benzyl Bromide O O CUCN 3'). m - fi.’ N+ or " ' —_> C | I Pg3 Organic Chemistry 345 Spring 2006 Exam 2b Name (Please Write Clearly) 2. Give the products of synthesis as isolated after workup a) - @000“ 1.HONO I NH2 2. FuranA - C b) Benzaldehyde ————* 1‘0"} A9(NH3)2+ . 0 <' > _ p C) i: Pyrrolidinei TsOH if; 0 Benzene distillation . NH'C'CHa 9.4.x d) : Dil HCI, A I 802NH2 ' e) t-Butyl +Bux “3 “‘ KNHZ, qu. NH3 ij “1 E? f) _ CI 0! _ Acetyl Chloride + Ethylamine—> ' ' ' ' o Fla 9) Ph-N=C=O + PhCHZOH ———> “I Aokw/ . . H h) Ph'fi'NHZ Brg, NaOH “’1 N H7- 0 i) Ph-CI=O Apgp NEtZ' LiAiH4, 1320' PM 2 . 0H- J) oH' Pg4 Organic Chemistry 345 Spring 2006 Exam 2b ' Name (Please Write Clearly) 3. Give the products of synthesis as isolated after workup o a) F ' s 1t ' ' m-Creso] M» H i.e. (K803)2N=O . o o I O b) ' 1 KOH NH _)_, NM 2) Methyl Iodide f O - M c) - ——> ' 4 promotoluene 1) Mg, EtZO @ 2) 002 (,0 H OMe _ 0H 2 d) —> W I HI A g + I ‘ Wu - e) Me Allie \nJ Ph-C-CH-S-Me p, II II AKHQ) )7 o o 0 - 0H + Dil. Sulfuric Acid A Cyclohexanone + 1,3-pr0panedithi01 —> . h I o “51' ) @730ch + Diethylamine —> 1 5 a ‘2— / N,N-Dimethy|aniline i) 3' Cl . 0 I J) . Q 1.Benzy| Bromide ( VP, (5 2. H20 workup if Organic Chemistry 345 Spring 2006 Pg5 Exam 2b Name (Please Write Clearly) 4. For each of the following put in the reagent(s) (over the reaction arrow) needed to give the indicated product. /CH3. . ,H a) 0 Hr, A O- OH OH 1)) Bra 0 Br \\ ll d) NH2 . HN—C-NH-Ph i ¥hflN=c=O 5. Which is more acidic, phenol or . Now draw the most important resonance structure accounting for this difference. GDCDH if G0 "54/ 6.Draw the mechanism of the Claisen Rearrangement ofcompound A. Give the final product as well as any reaction intermediates. As usual, put in all charges, unshared electrons and arrows neatly drawn. (Note that the CH terminal carbon is isotopic). :2 ©th 0 \ 4‘5» \ / 3 i H’ +TLV~+. 3‘ . ...——-' > J“ -——"9. l / A ' Pg 6 Organic Chemistry 345 Spring 2006 Exam 2b Name (Please Write Clearly) 7. Which is more basic, o—methox aniline or p-cyanoaniline? (Answer). Now draw the most important resonance structure accounting for this difference. Hiak’” : fr *9 8; Draw the mechanism for the Michael addition of Diethyl Malonate to the afi—unsaturated ketone B. As usual, put in all formal charges, unshared electrons and arrows drawing carefully. ‘9 0 Me C-CH—C—CH + D' —> 2 — 3 lethyl Malonate N O Et,EtOH WW 5 a H 0 E Big-9 L ' B 0 5+0) 061’ 0‘ o 451>/ ,,.fi7 EH0 ////:;g;;%; EwW: 1!} aw 06 or 9. Draw the mechanism for the reaction of benzoyl chloride with methylamine. Include the sigma intermediate. Include all formal charges, unshared electrons and arrows drawn properly. .. , - ,IML 10.A Compound gives a positive Tollens test. What does this signify? m COM ouncl wniutmi 0-" alfizI/h JC- (Answer). Organic Chemistry 345 Spring 2006 Exam 2b Page 7 — For Scratch.Use. Nothing on this Page will be graded ...
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This note was uploaded on 03/27/2008 for the course CHEM chem345 taught by Professor Zimmerman during the Spring '03 term at Wisconsin.

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2006exam2-key - L/e/j Organic Chemistry 345 Name (Please...

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