Final_Part_2_Summer_2009_h

Final_Part_2_Summer_2009_h - Chemistry 308 V1/V2 Final Exam...

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Unformatted text preview: Chemistry 308 V1/V2 Final Exam Part 2 July 23, 2009 Student Name (PRINT CLEARLY): Student Signature: SEAT NUMBER: InstructiOns PRINT YOUR NAME CLEARLY AT THE TOP OF THE OPSCAN FORM , WRITE YOUR EXAM FORM NUMBER NEXT TO YOUR NAME (FORM 1, FORM 2, FORM 3 OR FORM 4) Please fill out ALL of the information requested at the top of this sheet. Part 2 of this exam consists of 20 multiple—choice questions worth 1319, points each. ‘ To answer a multiple—choice question, use the OPSCAN form provided to fill in the circle corresponding to your answer. At the end of the exam, you must hand in the top sheet of this exam booklet together with your answers on the OPSCAN form. ' The length of this part of the exam, including time allowed to fill in all responses, is 75 min. Exam Form Number: 1 \ . Which organic compound gave the product shown when treated with sodium ethoxide in ethanol, followed by acidification to neutralize the solution? 1. NaOCchHs, CHSC HZOH i O O ? :———-—--———-———-————> v ' ‘ 2' HQ _ O/\ o o O ' O O O O D. NW E HJLHLOA 2 .. What is the best description for the compound shown below ? o OCH3 A a lactone B an ester C an ether D an enamine E an acetal 3 . . Which compound is the strongest base (2 points)? 09 90 O O . A M i 90 /\ H2N — C He ice OEt ' A B C D . . E 4'. What is the product, Z, of the following sequence of synthetic transfonrnations? 0 H6) v —HO + V 7 _.._______(__E_.)_._.___, x O O ' ——-—-—-—-—--—-—> Y X > + H®,H20 Y W? 2 C 3 Q Q N O. V O N A .' B ' C O ,o. o D 0H E .l O S- .. Which compound will be most reactive with sodium methoxide, NaOCH3 ? / . 0‘ OCH3 / \ _ \ ~ (1 N Cl 0 0 N02 B - D‘ E \ >322 / C 6 . What is the correct IUPAC nalne for the compound shown? A 4-nitrophenylmethoxyformate B 4»nitrophenylmethylethanoate- c 4—nitrobenzylethanoate v ' ' - OgN D ethoxy~4-nitrobenzaldehyde E ethyl 4—nitrobenzoate 7, . 'What is the major organic product of the'following reaction sequence? ‘ O 1. KCN ——-————-—————-——-———————-> ‘2 2. Add HCI to neutralize O . O HO CN OH f ,CN " ON CN % .. What is the major organic product of the following reaction sequence ?‘ O . 1. NaOEt, EtOH OEt ED 2. NaOH, H20 3. HCI, H20, heat 1} if?” 9-2“ OHV CN- OH » cl . Which is the correctly wn'tten mechanism for acid-catalyzed convcréion of an acetal to a hemiacetal? H O C H H 3 H C O H v / \ H30/ \CHg HsC CH3 H30/ \CH3 A o H/ \H ' me H: G ‘ HI ED H 0 OH H3c0\ /OCH3 H . H30CC;\(/O@C_H3 (00H3 H300\‘/OeH _H 30 \/ l B 2 22a— “""“ /C\ ' /C\ ‘ /C\ H 0/ \CH H30 CH3 H30 CH3 HSC/ \CH3 H30 CH3 3 8 H , ‘ 9 ' OH HsC GCHB OCHa H30 OH -H l C (2\ / __..__ C ______,_ D\ /@ _______ O\/ /C\ \ /C\ H 0 H30 CH3 HsC/) CH3 H30 CH3 3 o H/ \H H . ' <9 HCO 'OH H300 OH -H 3 / \ a \C/® __ \/ H CH / \ SC ) 3 ‘ HBO/>\_CH3‘ H30 CH3 ~Hsc (OCH D 0\C/ 3 o H/ \H 3 —-—-L. -——h-— W H 6) I I H0 OCH H H30 OCH OCH Hc . “300 O” E 3 Q I 3 qE/e V3 3 /0H ‘ \/ C /\ HsC/ \CHa HSC/ \CHS HsC/ \CHa HsC/ \CHS “30 CH3 ‘ Which molecule is aromatic? ", [:1 CG <1“ i i Q. Which reaction sequence will produce the synthetic transformation shown ? ‘OH 7 ———_———————> OACHQ ‘ A 1.SOC|2, pyridine 2. Mg°,Et20 3. Hgo=o B 1. Nagcr207, H2804 2. LDA,THF 3. NaBH4 o 1. P00 2. (CSH5)3P=CH2 ' D 1.NagCr207, st04 2. catalytic Néoa, H2o=o, heat 3. lJAIH4 E 1.30012, pyridine 2. KOBu‘, ButOH ‘2 .i What product is formed in the following reaction ? O 9 BI'Q, H, H20 CH3 > ? HO Br ' O . O — Br 0 _ - > Br . Br ‘ ' / p A B c D’ ‘3 . What is the product of the following reaction sequence ? 1. HNO3, H2804 2. Sn, HCI 3L NaNOQ, HCI. 0 '°C' 4. CuCN NHg NH2 CN N02 NH2 Q E 1 N02 V CN I CI ‘ . 4 . CN A B C ” s NO2 \4‘. Which ester would be hydrolyzed fastest by an aqueous solution of sodium hydroxide ? N02 .' CH3 \' I\ \ /C\ / \ / O\ 0/, .OCHs o/ OCH3 o/\QcH3 iWCHa o A B C D l5. What is the major organic product of the reaction sequence below ? “L NaOEt, EtOH . ' 2- . O i O M ' 'Br E‘O OE‘ 3. NaOH, H20 4. H01, H20, heat 0 o O o EtO OEt HO H30 A B C m 'Ho ‘ 6 . What is the major organic product of the following reaction ? O O /“\/u\ NaBH4 ’ CHBOH ‘ - > ? OCH3 - ' o O OCHs OH 0 . I OH O . OCH3 . 001—13 OH OH A B C D I E ‘ ‘1} . o What is the expected product of the Robinson annulation shown below? 0 NaOH, CH3OH, heat W '7 ' O O O ><IIK @ O ‘ o A B C D E \% . Which of the following is NOT anlintermediate in the acid—catalyzed hydrolysis of methyl acetate ? - e o CIDHz CIDH I A~ Hsc/IC\§__CH3 B Hsc—C—O—CHE C HeC—C—o—CHs OH OH £9 ‘ OH « OH D ('3' i ‘E H~c-—cl3—-(§———CH H3C/ \OH 3 I H 3 OH v- l Which molecule in each pair belowiwill have a o I o carbonyl stretch absorbance peak in its IR spectrum H . . (7 C or . at hlgher frequency. “ H30/ \(3 H3 H/ \H The molecules in each pair with CO stretch absorbances at higher frequency are: 0 o A 1,4and5 g or H B 2,3and6 “30/ \OCHa HSC/C\NHCH3 c 2,4and6 — 3 I 4 D 1,3and5‘ E 1,4and‘6 O O C O or ? m<:\o / o 2.0. What is the major organic product of the following reaction sequence? OH 1. Nagcrzo'z, H2804 my ? 2. CHgMgBr,EtZO 3. HCl,HZO “$90?th A , B ‘ c ...
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This note was uploaded on 01/12/2012 for the course CHEM 2347621 taught by Professor Mr.boikes during the Summer '09 term at Rutgers.

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Final_Part_2_Summer_2009_h - Chemistry 308 V1/V2 Final Exam...

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