Chemistry 3A - Spring 2002 - Frechet - Midterm 2

Chemistry 3A - Spring 2002 - Frechet - Midterm 2 -...

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Unformatted text preview: Chemistry SA— mwigTRfi} $131... “I'm” MthEiZ-M r2. __ seems “1,001... FEEClTE'T a Professor Jean Fréchet tour full si April 11}, mm Print your Middle) ‘four B|D_ Please check the section number and name of y. __ 151 Margot Pauiiclt __ 1?1 Danielle [lube _ 181 Matt Pratt __151 Laurie Sohenkel _ 4?1 Alex Koilias __ 111 Cathleen Yung ___ 411 Andrew Chi __ 121 Priya Sonik _ 421 Bhahed thghawala _131 Paul Furuta _ £131 Mike Slater _ 141 Zach Fresco _ 551 Jean Han _ 2s1 Aaron stutz art Dgnjen Miljanio _ 2?1 Vanessa Sun __ 511 Joe Kwon _ 211 Jamey Kain __ 521 Catherine Chan _ 221 Laura Anderson # 531 |Olga Fedin __ 351 Fteema Thalji _ 541 Jason Serin 3?1 Warren Wood It you are making up an l—grade, indicate the semester you took 3A D“ “m writ-5 in mi“ hm"- and the Professor This exam has 1E1 pages; matte sure that you have them all. We will only grade answers that are in the designated spaces. Plea do your scratch work on the backs of the exam pages. Write only g answer to each problem: multiple answers will receiye m credit. ey one of them is correct. Note: This examination runs for a total of Ed minutes. No questions be answered by proctors after the exam begins. Please write legibl] ambiguous or messy answers will receiye no credit. (£31 20132 J.M.J. Freshet, Berkeley. CA zoom. Freohet. Berkeley lt'jhem. 3A EUDZ Midterm Exam #2 Page 2 of ii] ‘it} points} Name {using [UPAC nomenclature} or draw, as appropriate. the following moleouies. Do not forget stereooherhistrg.»r tag; cis, trans, Rt 5, mesoi where appropriate. I".E:F.:lj'r-FL1TT'-U - 31...'F.'r‘ilurr-"'i--Ir| Warm-:- aunt“. to] {SR 34Ri-E-oromo—4-methyihexahe {Show as a Fischer Projection) (Shown here as a sawhorse projection} {a} {Rt-E-fiuoro—E—hexaool . L'- {Bi one J. Freohet, Berkeley Chem. 3A 2002 Midterm Exam #2 Page 3 of it] Add the missing reagents {and solvents. if relevant]. or products (snow stereoohemtstry where appropriate} {11 Points}. CH3 Hl—Br {:12 he ___—_—'h- Br H M hl ' E' Eli—ICC orina 10H CH3 at oaroonz Hint: are there one or two products? dzppzd. Freehei. Berkeley Chem. 3A 2%.? Midterm Exam #2 Page 4 of 1G {tdeints}. Add tits missing starting material. rsagsnts, pr products [shpw sterenphemistry ' where appropriate. note that several rsadtipn stsps may.r be required!) H «D 1] Listin HEC HI. 2} sq uspus work-up Jeane J. Freenet, Berkeley Chem. 3A RUDE Midterm Exam #2 Page 5 of it] eiBPomei weimmwmgmemmneenmemwdsymgheth1endeameamnmme [ Neoca3 CEH5CH2—(ll—Cl —"‘ CEHECH=C{CH3}2 + CEHECHg—LI.“=CH3 CH CH CH3 1 3 CH3 “In-r ' I Data: the concentration of the haloatkane is 0.03M; the E1 rate constant is in = 1.5 X 1|Il'4 s"; the E2 rate constant is it; = 1.3 X 10'4 L n‘tel'1 5'1. {i} Calculate the rate of each reaction and state which elimination mechanism is predominant with 1.5M NaDGH3. Show detaiieoi work and do not forget the units! Fiate of E1 reaction Rate of E2 reaction Predominant mechanism is: - ,i ll” {ii} At what concentration of base does exactly 50% of the starting material react by an E1 route and sons by an E2 pathway? Show detailed wort: and do not forget units! r.) Answer: J: 2002 .J. Frechet. Berkeley Chem. 3155 EDGE Midterm Exam #2 Page 6 Of 113' 5. {11 Points}. to} Propose a synthesis of thegfli} isomer of CHBCHNchECHa starting from {Rt-E-chloropatane. iii-3;} t.“ P .- i .. *0 1i:- ,, I 15-11 -. -_.' 'r . I ,_-. EV x" * fl 11th:" 1"'- 'r" 71-:1 —AI‘" to} Show clear structures for sit the products obtained in the following reaction and circle lie major elimination product. (Note that there is no need to consider anyr "rearranged" product} 'IIJ-t. H E) {5.} Ella N3 #5. . .L ' CH3CHE Bf —_———" _-- a I ' _ II I _ _ l'. ..1_ I CH3 In EtDH . I l. __.I all r _. J“ F-t'. I” re x F I El] 3 l H ‘nl' I- . 1.: II :I' . I ' f “5‘ Ill —5:’ I"\QFE': _ J | L ' ,e .s. ' ' _ -' . —J '13]? 'I-i'r E141" -' . II." ._ ."r 'r 'l— 'r‘. H H |.a_ F_—— ___E_ e zccz J. Freche'l. Berkeley Chem. 3A 2Dfl2 Midterm Exam #2 Page T cf 1D 5- {11 F‘OifiTS}. {3} Give the expected mejcr product cf each cf the following reecticne. 1|_.-.,‘. ‘5‘ | e . 'IEID 1.1'..'. . ' E- w CchHQCHED '5‘ CH3CH2C_HCHECH3 I.'_. G! EDHEJ. Frechet. Berkeley Chem. 3A EDGE Midterm Exam #2 Page 3 of it} it. {14 points]. Proyide a viable synthetic route for the product oeiow. You must start from the starting materiat indicated but you may use any other organic or inorganic compound in your synthetic scheme. (fHa CH3 0 Starting x" - —- -— ——I- — o'u rneterrair H33 T CH3 H30 CH; C\ Pro of CH CH3 CH3 3 “"4 'r I r. -.-'| u" -'=r U er; J i w I 'I: | «1 ‘L tJ-glfiflf". Jr -3- r I. IJ —l: fl'_:dr|1—3Y 1 - (.11: a . [in l'gc—c—r {Hemiifi " \.. E? in“, I i“ e 31 Vim d ' (we. I see i ' ...i iii _ I l - -.1 I.""'|l “5L ' E ‘ ‘ “gt-"ire? .L'J-Jr .. t'J-q . II I. ' I:- “I 3 'I-"' - II I 'r a wet-r” Ky;- E-yy ' ._ _z“" ' I ""-' 'I' 'l -- —- (H :I [I .- r J.“ 'I. \ rr-._. .I._ n " s- } I I I ,, iti—iZ—[letj—L‘I’d A. (it; {-43 "" EH; a [bi Propose a high yield synthesis o_f__3=octanet—stertiog.trom an aldehyde and an alkane ..---""'__ F . Hat-e. .e--' u'r'l “a Ir I In!“ r' — ‘V —:a git-Vii. farmer \ is {Lot Motor” [70 ' at I: e 'u- 29:».- 0 oil ll - H _ h iW‘H fir. {myrtlidr't-fih F EDGE .J. Frechet. Berkeley 8. {1flpoints}. Chem. SA 20132 Midterm Exam #2 ll.Nrite a step-by step mechanism {include arrows} for the reaction oetow. Show all intermediates. and explain {in the box} Wm,l the product is racernic. W i“ —-I- Explanation: the product is racemic because... -.':- ."'-U-’IrL- ’-'i i {It a." -'i " '-"'- Irllrif- J‘IHL’I r-rLI‘ . .__ {lg-II :' L1 .1".pr .- .-: I'. __';-u {racemic} 'tLrJ“ II.I t'J J'L-L'J _'_x Page 9 of “ID 2on2 J. Frechet,Earkeley Chem. 313. 21302 Midterm Exam #2 Page 1D cf 10 9- {12 Paint-3} (a) Show a detailed step by step mechanism [with curved arrows} exotaining the the outcome of the following reaction: CH CH DH “Ha 3‘2 " mm , Ft? a. ‘__..a"“‘~.\‘___.- Hckgjl ‘I l. i: - i' “hf "J I i 5» rat'- _ 1 .-.__ "I _*-~-.. " ' E I F“. |'.... I. -_ “hik- /,r EL. " .-|.=- ._/J'l. [TI/‘1. to) Show clear structures for products A arid B in the reaction sequence below: rs nor-i s} ace in CHECIE 3} QM in ether CchHgCHgCHECE ‘3 H20 -- - 1] CrDE H 2) LiAID4 in ether 31mg Hgo ...
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Chemistry 3A - Spring 2002 - Frechet - Midterm 2 -...

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