Exam_II_Key_Summer_2008

Exam_II_Key_Summer_2008 - Chemistry 308 _ Exam 2 August 4,...

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Unformatted text preview: Chemistry 308 _ Exam 2 August 4, 2003 Student Name {PRINT CLEARLY): Student Signature: I Section Number {H1 before leeture, H2 after lecture): SEAT NUMBER: LB Instructions PRINT YOUR NAME AND SECTION NUMBER AT THE TOP OF EVERY I’AGE. You will get no score for the pages missing your name. You will not get a copy of your exam if the pages are missing your section number. Please fill out HALL of the information requested at the top of this sheet. This exam consists of 5 multiple—choice questions and 15 questions requiring written responses. To answer a multiple~choiee question, circle the letter corresponding to your answer. Questions requiring a written response should be answered clearly and leginy and only in the Space provided. Please answer all questions within this exam booklet only. At the end of the exam. you must hand in this complete exam booklet. Do no 'e arate an of the sheets in this booklet or re ove the 't . Do not hand answers in on extra sheets. The length of the exam. including time allowed to fill in all responses. is T5 mitt. Exam Form Number: 1 PRINT NAME SECTION (H1 01' H2) 1. The product of a Rabinson annulafion is shown balow {a Michaal additinn followed by an intramolecular alan candensafion}. Draw the: stmctures of the: 131: organic compounds used in this reaction {3 points}? 0 (fig CH3 0 NaCIEI, EtCIH. ht ex 0 q ______. "s ‘ \j, C! 1. “'1 ’L 0%: ups 2. Draw the structure of l—mtthylflthyl propanoatc in the spam: below [2 points}. \Ao)\ th 3. Draw the 111m most important rfisunanca forms of propanamédc. Indicate all furmal charges clearly [3 paints). (3% 39*! H \AW 53 a 0%: Total points this page {max 3) 2—3,? PRINT NAME SECTION {H1 or H2) 4. Give the reagents necessary to perform the synthetic transformation shown below. Number the reagents for separate reactions, as usual. Partial credit will be given for incomplete answers. only if intermediate products are indicated {3 points). o l 4 {KG-1.916%] 1.; on 1. Hi" 1 H19 2 0+5. 31 Nfi‘m‘i‘) CREE,“ CH3 an. a 3'. enter; , a. H ma) - lat if we“ e12. W’ 3. H1 J mega (PM “‘3 5. Draw the structure of the product of the reaction sequence below (2 points}. l: 33% / \ / we. ~\ N“ ———*—- '3 %' A 6. Write a detailed mechanism for the reaction shown below. Use arrows to represent all electron movements, show all intermediates, and indicate all formal charges clearly {3 points]. z" 0 ‘3' E“ion, Hgo o M ' 44$) A gifrs ‘ What \hM-L ark G (2 Total points this page (may: 3} = rm 1 WV” )‘K a?) EPIC. PRINT NAME SECTION (H1 or H2) 1’. Give the major organic product expected for the reaction sequence shown below (3 points). o 502” 1. soon. heat lit-babel l\ Q /\ —.— a 2. onscnzon Q 3. Draw the open chain Fischer projection for the carbohydrate that is shown below as a Haworth projection (2 points). (at) CHEDH l'l VG HG o oH H at} H e‘Ft OH OH camo‘ct 9. Give the reagents necessary to perform the synthetic transformation shown below. Note that there is an extra carbon in the carbonylic acid product. Number the reagents for separate reactions, as usual. Partial credit will be given for incomplete answers, only if the intermediate products are indicated (3 points}. oH L new I Draw OH AA. we: Mei ’5 it DH ’2. “Mahatma A Total points this page {max 3) = PRINT NAME SECTION (H1 or H2} lfl. Give the NAME of the functional group that is clearlyr indicated by the IR spectrum shown below [2 ' points}. ' NAME OF FUNCTIONAL GROUP: Cm elm-TEL} C" FDva 1“ l \ u'F‘I'fi'E'E‘fi'H‘H'! ':' '.' ‘1‘ f 'r' E i l i‘ F '." E" ‘3 '.' ‘.“.."‘.'¥'.".!‘*" . . . L" I all I an I I 1: I -u ' -u I- -u l -u nu _ NEAT fl m- aul 1|- llin Isi— Im' II I- all“ Immune - Hmmmn-In 11. lIl‘ra'ar the structure of the major organic product of the reaction shown below (3 points). Fl *3 NaBHCNHD Q O A =* A <\ E}- {Fmr 12. Write a detailed mechanism for the reaction shown below. Use arrows to represent all electron movements, show all intermediates, and indicate all formal charges clearly {3 points}. tea _ NaDH,H20 U *OCHE i053. + HooH3 ’gEi-g (a 1» U H a _ ~\\‘ (30 {:5} 0H3 ficrij H p Total points this page {max 3) = *1“ figs 5 J'D PRINT NAME SECTION (H1 or H2} 13. Draw the CINE resonance form of pam—nitropheny] acetate that EESI explains wh}r this is an acflvg ester {veryr reactive with nuctecphiles} (2 points). , D 0 QB DE) {9 __._ i D 63“ KG 1—... ‘i‘ II— :7 N / ego ‘ 2:" “a \ GE) 14. Draw the structure of the compound that gave a strong peak in its IR spectrum at 1T4t'} cm", and gave the “(I—NMR {top} and ‘H—NMR {bottom} spectra shown UN THE NEXT PAGE [‘3 points}. 0 Q\g/\ f7)? '5- c \ €11 Est vix/ 15. ISrive the reagents and steps needed for the following synthetic transfcnnation. Note that a protecting group must be used. Number the reagents for each reaction separately. as 115L131. Partial credit Will be given for incomplete answers, only if intermediate products are indicated [3 points}. 0 0 STRUCTURE: DH Total points this page (11131 3} = PRINT NAME SECTION {H1 01' H2) 'NMR spectra ef unknewn eempeund from previous page: 16. Rank the compounds shown below in order Elf their nucleuphile strength {3:- means "greater than "J. m: the answer {2 points}. HSC CH3 a O OH \N/ AIsIIsIn CIIsIsIn Dusms] Elusisn lT. 1|Ir‘lr'l'ii-sh of the structures shown beluw is NUT an intermediate in the mechanism fur acid—catalyzed hydrolysis of methyl acetate. Q11]: your answer (2 points). DCHa 0H s - I (some I @0H 30H 2_ Hac—(f—UH i HEB—(Il—OGHQ A A A B C D E ' Total points this page (max 4] = PRiNT NAME SECTION (H1 or H2} 18. ‘Mtich chemical argumenfis} BEST explain the greater reactivityr towards nocleophiles of simple aldehydes compared to simple ketones. Circle your answer [2 points]. A inductive and resonance effects B hypercoojugation onlf,»r C inductive effects only ’2_ D resonance effects only (E hyperconjugafion and steric effec 19. What is the major organic product expected from the Mannich reaction shown below?I fimlg your answer (2 points}. ' O D l. HC],CH3CH20H,heat + A + H2NCH3 —1I" ? H H 2. KDH, H20 to neotrahze 0 “xx / G \JKA “ L “l / N/ “a. I W a _ 13- RN V'H/ 21]. Which pair of compounds selecfid from those below is expected to react together when heated in base to give the best yield of the croSsed aldol condensation product? fine]: your answer (2 points). 0 o 42,; jv \i/ OAH YIKO - 1 II III IV AI+II BIII+I Cl+I"rr EIIl+I"Irr Total points this page (max 5} =¥L ...
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Exam_II_Key_Summer_2008 - Chemistry 308 _ Exam 2 August 4,...

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