chem312 s03 exam2

chem312 s03 exam2 - ./ EXAM2 Chem BIZ—Simek May 9, 2003 W...

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Unformatted text preview: ./ EXAM2 Chem BIZ—Simek May 9, 2003 W 1. Be sure your exam has 5 pages of questions, none blank. Wiite your answers directly on this exam. 2. A periodic table is at the end. 3. You may use a writing implement. No calculator should be used. 4. Please, scrupulously avoid glances at other exams! 5. If you have a question during the exam, raise your hand and the instructor will come by. 6. If you finish early, please leave as quietly as possible. ortho,para-directors: R, OH, 0R, NHz, NR2, halogen meta-directors: N02, C=0, SO3H, CF3, CN M m l [10 2 [25 3 I35 4 [25 5 ‘ [30 TOTAL [125 10 points) Shown here are segments of two polymers. Circle the structure of the monomer t would form each polymer. Note that NONE OF THESE is a possible answer. a. H3C0 H300 cho l H3C0 H3C O . k circle the correct monomer H3 k w NONE OF THESE IS THE CORRECT MONOMER \i wavy lines mean a \ continuation of the polymer chain Cl \ b. Cl (:1 Cl polymer Cl Cl ' MC] ) Cl ., circle the correct monomer Cl Cl C] NONE OF THESE IS THE CORRECT MONOLJER points on this page __ 110 cm 312, Exam 2, p. 2 Initials 10 points) These are natural products. Circle YES if the structure is a terpene. If it is not a e, circle NO. OH H y. °“ @ me ‘ é YES NO TIL YES NO COOH YES NO . YES NO , YES NO A % 3. (10 points) If the compound is likely to be colored, circ ES. If it is not likely to be ’ colored, circle NQDCH3 W _,. 0 CH _ NHZ * 4. (5 points) Circle the structure indicated by the name. ONLY if the 1 structure is not show, draw the contact structure in the box. /wmx ' 3 t-BUTY -S-ISOPROPYLTOLUENE ‘ lFANYST CTURE APPEARS IN THE CH BOX WH N THE CORRECT STRUCTURE 3 APPEARS ON THE RIGHT, NO CREDIT , WILL BE GIVEN points , this page W 125 Chem 312, Exam 2, p. 3 Initials 5. (5 points) Circle the correct name of the structure. If the correct name is not listed, write the correct name in the blank. galore alphabetization of substituents.) tam—01¢" CW g-efliexyadr-isobutylbenzaldchyde COOH- , ' _ l‘ 5-sec-butyl—3-ethoxybenzotc acid 4-sec~butyl-2-ethoxybenzoic acid IF ANAME IS WRITTEN EN WHEN THE CORRECT 5 NAME IS SHOWN. NO CREDIT WILL BE GIVEN v 20 points) Circle the answer. \g incle the One structure containing the most stable carbocation. ® CH CH CH CH 6) I 3 G) / 3 l 3 x 2 CH2CH2 -- CH CH3CH — CH CH3CH2 — CS) CH3CH2 - CH \ \ \ CH3 CH3 CH3 CH3 Circle the one structure that wi 1 an rgo Electrop ilic Aromatic Substitution most rapidly. gh——7 '0 0 O 141/ o * @ Circle the one structure fllat will undergo Electrophilic Aromatic Substitution most slowly. coma n00 QM» H % Circle the one arrow indicating the site where an electmphile will attack fastest. 'OH OH [j/ Dams ” Hid“ . . cw ’CH3 *7@(10 points) This is the structure of quinic acid. founé-irrtlie leaves and bark of many plants. or each of the five carbons indicated by A-E, determine whether each is a chiral center or not. E carbonA 22> chiral < not chiral D ‘ carbon B 22> (chiral } not chiral H0 COOH \m +— D carbon c r-_-.:> chiral carbon 1) i:_.-_::> chiral (5%} H0 H OH carbon E ¢=:> chiral not chiral 3 CH C points on this page 135 Chem 312, Exam p. 4 Initials (ff—J , ,,_.._.r.r,, .<_. .. _.. a" VW___ —-———-—-—"'—“‘-"—-——' 8. (25 points) Complete the reactions by filling in the missing reactants mm are requested, show only organic products. Show only the major products unless otherwise indicated. \ “gr/111042 a. H20 com major organic product A)? ©+ I .__.. O FCBI'3 % Q + Brz -—~+ major organic product 0? AICI3 Ho OH + CH3CH2B1- —-— major organic product Ci *9 + _._.. starting aromatic compound, benzene with one substituent NO2 reactant and catalyst points on this page [25 Chem 312. Exam 2, p. 5 Initials (10 points) Answer these questions about the stereochemistry of this structure N. 2v 1). Does N have a plane of symmetry? YES NO a. How many chiral centers does N contain? c. Is N optically active? YES NO _.._.—- d. Does N have one or more diastereomers? YES NO .__-v {1 If N has one or more diasteneomers, does any diastereomer have a plane of symmetry? YES NO ’ (If you answered NO to part d.. then leave this question blank.) A? (10 points) For each pair of structures, circle whether they are enantiomers, diastereomers, or ' ‘1 e same. Br 1 Br enantiomers \f .nCH31 H39» ' H CNN a. CH3CH2-E{ ' 5-: yoga-1 mate?“ NO -a(Q/V same 3 CH 1.3.; Q U)“ H H . H I CH3 H \ I CH3 enantiomers Br CH2CH3 CH3CH2 Br same structure F F i . .. t __ _ a 11. (10 points) Deduce the structures of the mystery compounds X and Y. (Inorganic products are not shown.) Draw their structures in the boxes:_§Work backwards to Y, then to X.) ‘ H2S04 0; o o X T Y W H (3611120 C Gal 0 workup ID x, CGHIZO Y. C6H10 points on this page I30 Chem312—Simek KEY TO EXAM 2 Ma 9, 2003 H CO Cl @womers a. 3 diene monomer, not shown, b. alkefle \ NONE OF THESE was correct Cl monomer Que first three were terpenes. * 0H * * * * Two were not terpenes. 0H * x * 2: COOH 10 carbons but not perfectly divisible we top two structures would be colored. The two that had s133 atoms in between the sp2 atoms not be colored. st-Bms-ISOPROPYLTOLUENE was the lower right structure @- —sec-butyl~2-ethoxybenzoic acid COOH l 2 OCH2CH3 4 3 a. the most stab fastest to do slowest to do ptically active carbocation is ost AS has the most AS has the most = the structure with highly substi ted activating groups deactivating groups a chiral center 0H CH3 . It 3° CH3 "CH3 n electrophile wil attack fastest on i e ring with an activating group H300 O O COOH (OCH3), and ortho to that group since it is an ortho,para—director *Qchiral centers E spz—not chiral 9. stereoisomers £ 1-10.” Br H0 Br CH2—not HO OOH A ——-—a- ‘\ CH3 as mom“ CH3 C and 9—H“ THREE chiral centers (*9 no . , plane of symmetry, H0 1 0H Ch" 31' as two optically active, diastereomer by inverting one CFC Paths around the chiral center; many diastereomers possible, none hi all; Ung “‘3 the same of which has a plane of symmetry c 1' Problems 8, 10, 11 on next page. Chem 312, Spring 2003. Key to Exam 2, p. 2 % Complete the reactions. OH 0H & \ KMnO4 V KMn04 makes glycols cold 0 0 AlCl3 + -—>~ F fiedel—Crafis acylation a C] beginning with an acid chloride 0 F3313 brominafian; C=0 is a meta-director ® + Brz HH—‘b- F riedel- Crafts CHZCH?’ alkylarion; it doesn't ' AlCl3 matter which portion @ HO OOH + CH3CH2Br —--- H0 ou the ethyl group goes on as all are equivalent here Cl o,p-director makes a dlflerence; ifyou , this was the example we did + C12 CL in lecture to Show how the Fee] *-—-I- sequence of reactions N02 3 N02 '—.—"——.—""-""— _ want meta, put the meta startm g aromatic compound, 1330mm m—director director onfirs, benzene with one substituent catalyst a. mirror images of each other, but no chiral center; they are the same structure w b. H (hidden) carbon are chiral centers. 0n the night Newman projection, the front carbou is the mirror image (inverted), but the back carbon has the H ! CH3 0n the left Newman projection, both the front carbon and the back CHZCHS same configuration, so these two structures must be diastereomers. Br . F fie 11. The ozonolysis of compound Y was given as a practice problem on the fill-in lecture notes. 0 all C of ozonolysis x Eégi Y t—h-E-l—i-s-ua-al m product in a chain, so 1" CGHnO A COHm workup H must have been a flag work backwards: remove oxygen X H OH 6 S 4 A 0R 4:22: I) 3 (:3 N CGHIZO I 5 4 3 1 H H OH H H H Y2 6 “12 C X has H—OH more than Y, so the X to Y reaction reconnect 6 .two must have been a dehydration with acid and heat; C611“) 333° Czo With a in X. the H and 0H have to be at the positions of two units of " the dauble bond in Y unsaturation, 1ring+1C=C Chem 312-01 students, A breathless world awaits .............. .. the outline of Exam 3, Tuesday night. MSW . €50 m 6 pts) colored 41. (8 pts) Match each of the four structures with its pesticide classification. com ounds (like old exam 2, problem 3) 7 id OW UL Q J@( vmnfl. "mtg _ " A. (4 pts) nomenclature; given a name, circle its structure (similar to old exam 2. problem 4) J1. (10 pts) indicate chiral centers (like old exam 2, problem 7) {1’ V‘- 1 2? -/- 5. (10 pts) questions about stereochemistry (like old exam 2. problem 9) 6. (8 pts) Substitution and elimination are competing reactions, especially when the leaving group like halide is on a secondary carbon. Show the products of substitution and elimination from this starting material plus NaOH. If more than one isomer can be produced, indicate major and minor. \f 7. (9 pts) Circle the correct answer. (miscellaneous like old exam 2, problem 6 or problem 10, or old exam 3, problem 3 or problem 4, or maybe like none of these) % 8. (20 pts) Complete the reactions. Several of these are taken directly from the text. That's all there is. No surprises. , egg w ...
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This homework help was uploaded on 02/07/2008 for the course CHEM 312 taught by Professor Bailey during the Spring '03 term at Cal Poly.

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chem312 s03 exam2 - ./ EXAM2 Chem BIZ—Simek May 9, 2003 W...

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