Practice Prelim #3 key - NAME CHEMISTRY 1570 Summer 2009...

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Unformatted text preview: NAME CHEMISTRY 1570 Summer 2009 Thursday July 23". 2009 11:00 am. - 1230 pm. PRELIMINARY EXAM #3 Please do not open this exam booklet until you are told to do so. You will have 90 minutes to complete the exam. Page i 1 (20 points) 2. __ (15 points) 3. _ (20 points) 4. __ (15 pointS) 5. _ (15 points) 6. __ (15 points) TOTAL Excluding this cover page there are6 pages in this exam. 1 . (1 0 points) The reaction of acetic acid with thionyl chloride gives ethanoyl chloride as a product. Please show a mechanism for this reaction. “Sc 0” _S£°'2_. n \OH 0 ,C\ O m r {3‘ OH H ll C t , C {fl / \ I ._> / \ - (H C _ ,7 7 H. C ‘ t \_ fl 3 '9 S‘EO H3( _> H (/f()l / 1 6/ ,5'\O r" J r IT ‘ / ' O i (1 CC ll r‘C 7‘ 2. (10points) Aniline has a pKa around 5 whereas many alkyl amines have pKa's around 11. Draw the resonance stabilized structues of aniline to account iorthisfact L / (brill? 63,1“) '9“; E (j G ll (59H A? ,. ll ,» [J H L) s/l Aniline Page 1 3. (5 points) What product would you expect from the reaction of a cyclic amide such as valerolactam with LiAIH. ? H H N H o 1. UAIH. \/ I —. I 5. (10 points) Methyl phenylacetate has a strong odor similar to honey. it is used in the flavor industry and in perfumes to impart honey scents. Draw the resonance stabilized enolate ion formed when methyl phenylacetate is treated with sodium methoxide. '— “2 ‘ O/CYO-Cha Na’ 00H, 1 5 ,7 # I o T / Show the product of Claisen condensation of methyl phenylacetate in the presence of sodium methoxide. (You do not have to show the mechanism). .—-1‘~ Show the major compound produced when this Claisen condensation ester product undergoes saponilication followed by acidification. then decarboxylation. 6. (5 points) Show the product 01 a base catalyzed aldol reaction oi the following molecule prior to dehydration. (You do not have to show the mechanism). \, O H O ‘ l I i a cu -c Mon iu H~ CH « « 20 ‘H —— c’( CH“ ‘ / H i \rfl/ 0 OH 7. (5 points) Show how to convert this alkyi halide into a carboxylic acid. 8. (10 points) Show how to convert this alkyt halide into an amide then an amine. Hz-N'FCHa H~CHa —>—> —> Aidmi (u ,_L;fil“; 1 [ff/.1“ a ~ x f 7 i350 . xi H J 1/ l/C\ Cu / /C\ [T ZuulCLia l/ /C \ \ ' a i l Mr» \ i \ / €06? ' / “ / Page 3 9. (10 points) Draw Fischer projections for the product formed with the toliowing. State whether each product is optically active or optically inactive. N18014th _> HO HO H JUQL; H H WOH D-Mlmoee Wshmafizo _b 10. (Spoints) PieaseoonvertD—guiosetanisdier u \C¢[ €1.11 f“ H o H g (H H 4 ” H rt 1“ m V De. :4 (“J Cu CH Page 4 ’ I 11. (15 points) Please complete the following reactions by drawing the expected major product(s). o H 0 (1L, g \( / .J \O-CW /,1 ‘ / ' \ L CW. m l/ l ( ' 2. up «3.x 5 0 O I l I/« o o ‘ / ‘- OH c‘ocn, 1me. //’ /(“-.,(w“ “(L7 2.H,o~ L J " HOH OH I-Lo cnaon N (“W 0 Ho OH ‘ \/g (u H H u {a \/\r‘u .3 H to \m/ (H C\ Page 5 12. (15 points) Please indicate the reagents needed to complete the following transfonnations. W. o 0 9 0&th on ’3‘ 04, con. I C C “30/ \w' '3 ‘ f A q 4 W-coo “1‘3 HO H , 0 u 111% 0‘0 OH OH ,4 A I OH \. 41C yg/j W )cusm‘lz mtg—cu, 9 c‘ - 0/ CH3 4”? Ni(lL-( CHCHS —> o o a u 0/ con, NaCH ORG” HM —. CH, CH; [jag/W H mm, (jé’c’w‘ O 2;. ;:‘,0‘ ‘y Page 6 ...
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Practice Prelim #3 key - NAME CHEMISTRY 1570 Summer 2009...

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