Chem 242 Exam 1 Key - I 5 t KAy// CHEM 242 EXAM #1 (80 pts)...

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Unformatted text preview: I 5 t KAy// CHEM 242 EXAM #1 (80 pts) Name July 25, 2011 TA 1.a.(8 pts) For the following 2 step azo dye synthesis fill in themissing structures of the diazonium salt and the azo dye. r” ‘ , 3 Reaction #1 “553;; ov-lkza +0 0cm) \ ,Cd} Br N \ U “ who. N‘“ , Br —. DU 0 I CNS H H\N,CH3 \N + NaNo2 ———;—> g WN‘ :MEM ' ® . primary amine Activated aromatic I : .Diazonium salt Azo dye b. (4 pts) The type of reaction mechanism for the second step of this Azo dye synthesis is (choose one): 1)Aromatic Addition reaction 2) Diazonium substitution 3) Dyer maker reaction «.2 V iii? Quit, - @lectrophilic Aromatic Substitution 5) Nucleophilic Acyl substitution 6) 8N2 .«f “'13:” =. 1 «'» 2. (4 pts) Circle the compound(s )below that would be considered azo dyes. //——\ hu‘l‘ rung CUWJl/lg ai‘ccl Q I H \ N§N/\© NW b. (4 pts) If water had been a containment of this reaetion what other product would have formed (draw the structure) \ O ’COTM Carbaxjhk at ‘91/ c (4 pts) In the derivative procedure above, pyridine is often added to the reaction mixture. Explain why the addition of pyridine might be beneficial for the derivative formation. ’ N i or . - I It \ \S (A steel +1) Mui‘vAlig/Q Hm ,g 1(‘Whmb/ Dmnng MAC/Hm H / A ~/-’—\: H C\ 6 ) k) N pyridine / WV), Mmol’ Unit“ {13me and? \% 'R/M Mott/Fun} (AA—H“ Otcwi Chlbvich ‘W @ NH /\ 3 / i ) Have] I”? y) L i,’ . I._ _ (Av/taught“ i-OWN’I} dual chloriu‘ l t\ -;_Iy. 4. (6 pts) If you wanted to synthesize the Ester below, which th compounds (from A-G), would you react together to form the ester?____§_iw “ - r - ~. . v ‘ Answer Questions 5-10 using compounds ATH heldwfi \f'r _ O O ‘_ HO CH3 . . NHz HO\/\/\n/OH (:(li\NH2 O . A B D C CH3 ' OH 0 CH3 N\ OTCHa ,I r: i / O E F H 5. (4 pts) Which compound(s) would give a positive Ferric hydroxamate test? H E esifiyS . ‘ o i 6. (6 pts) Which compound(s) would turn chromic acid solution from red to green? A g F l ‘ 2 m a OH “\5/ NOLAN dd) 7. (5 pts) Which compound(s) would be soluble in 1 M HCl? ‘ AM‘NS I E ‘5 cm “W V‘ 0+ E’an L 8. (5 pts) Which compound(s) would be soluble» (SodiuIn bicarbonate)? '3 A 0‘ “015 l 9. (5 pts) Which compound(s) would react with 2,4—Dinitrophenylhydrazine (12,14-DNP)? C) i‘ ’QTCM-L /A ioLtLq d4, 10. (4 pts) The 2,4 DNP derivative(s) formed in question 9 above are‘colorful yellow/orange solids—briefly explain why they are so colorful. \ 01/ J N Tl“ , v J/ LL QY-e i/M id [0“ u + I 4”..- NH El 7 a J 1A1! 51,572“ P ‘P— ¢ \ l I “01/ ’ y ll. (3 pts) Which compound(s) are esters that could be hydrolyzed by base (NaOH) b. (6 pts) For each ester draw the products of the base hydrolysis below--assume the product mixture is at pH 12 ). / ?LW‘O\ jOUP-vofl‘mabg 61+ pr-l 17/ c. (3 pts) Circle the structures above. that would be soluble in the pH 12 solution Ale ...
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Chem 242 Exam 1 Key - I 5 t KAy// CHEM 242 EXAM #1 (80 pts)...

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