Exam3Test4 - Chemistry 322aL/325aL 3 M*2— Name Exam No...

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Unformatted text preview: Chemistry 322aL/325aL 3 M *2— Name Exam No. 3 (1) (15) Complete the chemical reactions below by providing the missing major organic product within each box. You do not need to show byproducts of the reactions or any mechanisms. Provide stereochemical details in the products wherever they are important. “' + (A) CH3CH2CH2$CINEX + CH3} mama; aloe. (LC-H5 (£143 + .. (8) 'v‘ + Na CN 1!? \CHZCI CHZCH3 singie enantiomer CH2CH26H3 (C) CH3 I‘h. K20 CH3CH2 Br Acetone single enantiomer H g 3 moor-23 (‘13) C Br, 3 \H (Si-1301:“! CHQCH3 single enantiomer (358120 singie enamiomer 3’ _ H20 (E) H + H0 Acetone (Cfiah H Mia/gal?“ Cm ”141”“: “mama ”twee! w+ Le Chemistry 322aL/325aL ~3~ Name Exam No. 3 (2) (15? ”2‘ 446A— wfmflvfif Cc‘Wfq/. N:y+Z/€ (A) (10) Circle the structures beiow that are chiral. W CH3CH2CHCICH2CH3 2 CH3 5? (PH. W3 enscmzccea CH3CH2CHCZCOOH (CH3)2CHgHC}—{3 CHfigizoz-i e . a o CH3CH2CH(NH2_)COOH .\ . CflaéCHZCMZCOOH (B) (5) The compound ibuprofen is a wideiy prescribed anti-Mammatory drug. It is chirai but only the S enantiomer is physiologicaliy active. Place an asterick (*) immediately above the carbon that is the stereocenter in the structure below. In the box below, Show the arrangement of the groups around the stereocenter in the S enantiomer. Follow the directions in piecing your groups around the stereocenter. H3 ' @550 m9 Leo-5m CH3 HCHfQ‘E-IKHflCOOI—I gfl— - Ibuprofen CH2:CH§H-B¥CI~13 Chemistry 322aL/325aL - — Name ExamNo.3 ()— ”SIMC'Z/ (3) (20) Circie the answer that correctiy completes each question or statement below. (A) Among the foliowing dimethyicyciobutanes, H3 H3 (283 CH3 CH3 CH3 CH3 I 1:: 111 IV -I and II are chirai while II and IV are echirai. E -onl I is chiral. ._ m all are ac zral. The next two questions refer to the three structflres beiow. OOH 00H 00” 1-1 OH H OH HO H e H H 01-1 H OH I II III (B) (Circle the correct 5£atement.) ~A1E three structures are chirai because they ali contain stereocenters. « ulna-D -AZ1 three are ac ira. ~I and 111 are achiral while II is chiral. - I «.. II are related as (ii __- .. - .__._ ere whiie I and III are related as enantiomers. ~I axzd III are related as diastereomers whiie I and II as we as are re a ed as enantiomers. -All three structures are related to each other as diastereorners. «A11 three structures are related to each other as constgmtionai isomers. (D) Opticafly pure (R) glyceraldehyde has a specific rotation of [aha = +8.7”. A sampie of giyceraidehyde that shows a specific rotation of [0:15 :2 «0.87” is a mixture of the enantiomers of glyceraldehyde that is 19% 8 anti 90% R 60% S and 40% R 55% S and 45% R 90% S and 10% R (E) The stability order of the carbocations below is + + + emcezcmcuzcas enscnzcnzcezcez CH3CH2$CI~13 1 ' . 12 1x1 CH3 I>II>III 11mm biibfl '@ Wan—MWMMMMMMMWWMW..WW.M_W.................... . Chemistry 322aL/ 325211; -5- Name Exam No. 3 {3) Contd. _ch:f RT (F) For a bimoiecular reaction, the factor 9 gives "the rate of'coliision or encounter between reactants. _ v e fraction 3 - 1510115 w ere reactants are sufficiently energized to reach the transition _ State. ~the difference in free energy between the reactant and product states. "the height of the energy barrier between the reactant and product states. (G) Among the soivents below, 3? CH3CHZOI~I CHsC-MCHsh H20 CHs-S-Cl‘is I H [:1 IV ~« 0131' {1 Bi are oiar rotic and II and W are olar a rotic. ~E anti IV are polar aprotic and {I amt III are poiar profic. ~a11‘are polar protiC. (ii) The reactivity order of the (2ng compounds below in an 5N2 reaction with CH30' is CH3-Br CHg-F CH3~I I H :11 b31>III room now: (I) The relative reactivity order of the following oxygen nucleophiles Cch-d (3‘13 “0 CH3O I {I 13 room I>III>II {Eb-[bl (I) In the reaction below where Nor is a nucleophile, in an 8N2 reaction is R-X + No? R-Nu + X The initial rate of the reaction quadruples (increases by a factor of 4) when both [RX] and [Nuz'] are doubled. The rate expression. for this reaction is rate «“— kiRX]2{Nu:“]2 k2[RX] 2[Nu:‘] kIRx14 Chemistry 322aL/325aL ~6- szam No. 3 3 (0 fi 616 A/ Name (4) (15} Define or explain with an example the following terms. (A) Achiral _ A S-kucfiLA'r-um Ohm \fg Mkr-r-wr- kmfixfifx Us. upom Wk. (DPTSi‘Ma-L.\- A)?“ br‘ A- $+r~mcwr¥14xrg 1...: \~\-\,-\ <2.k pkg-“1‘ Q-G S‘uMM “q. (B) Racemic Form P? mwmw CL'V-xa M‘k—E'OWN" 7‘33 SRP" t“ E‘Mpoaa‘o!‘ . (C) Waiden Inversion gml MKLHDM. /. \ fl _....._——> ”Cu 1 £9 HiMX Nu \U (D) An Endergonic Reaction A Maw“ gum m sfiwkaha‘ Gm “W7 @on—mSK; AGO”, x": 1203;“qu ‘ ' EDP {3w PLch‘FrD’h (.3 kfiW/‘k Wk fi>POClULL+ €+u-$k SS fibewfi "HM!“ mmflfim'l“ S'RJKL \")'\ k 'ng anm-J dimgmwv (E) The Hammond-Lemar Posmlate as it applies to a highly endergonic reaction \% Ox ‘n'TSFMK/ fimdaréom‘ic raged-19ml, T‘L‘x‘ Mmsgfinm afid‘k S-khucw'k'ikr‘qx Mg: «Nb-k3 "\‘l’vm sA‘TUQMFL 0'6 W Pr‘OCJkA-hq'sr‘ (~3wa ”OWL— Q—«LGK947 “mm-K +~k§ mk.m.‘1¢&.-y\j——- 3% , cor ”Pkg“ framSH-W’K Shi‘k <10ng \cfi‘fl 5.30%} “HA vmacA—iom qaorcfiwflh (”ASL ‘13 Q\D~S9r\ 4—0k4r4/«Q. PT‘OCJU «1'1“ \$+-a:’t~¢.. Chemistry SZZaLXSZSaL ~7~ Name Exam No. 3 (5) (15) Answer the foilowing questions about nucieophilic substitution by way of the SN} mechanism: _ ' 5N1 R3C'X + Nu: R3C~Nu + X” (A) (2) Draw the structure of the transition state for the rate determing step of this reaction inside the square brackets below. # 5‘4— 5— R5C“"X (B) (10) Complete the table below by indicating the expected result on the reaction rate for - the indicated Chan e. ‘4 1‘ ”MW Effect on Reacnon Rate Tem era’mre is decreased :m cm Mes Soivent is changed from iess poiar to more ooiar Y‘cdvk \‘h‘l MCL$¢5 Leaving grou is changed from C1 to I we m m w s (C)( )(3) It IS weii documented that the stability of carbocations increases as methyl groups replace hydrogens around the central carbon Relative Stabiiity: (CH3)3C+ >> 33C+. Expiain with an appropriate drawing inside the box below how either the inductive effect or hyperconjugation accounts for this observation and indicate which effect you are describing on the tine below the box “W W. chm-howe- A 69/ GAS ewe“ Meme ‘ «to A (MAL ?0\£~r \‘ULS. ‘ §\§W\¢\ Q..\:LL \ Chemistry 322aL/325aL —8- Name Exam No. 3 (6) (15) Heating (3:). 1~bromo-1wphenylpropane in methanol produces (i), l-methoxy-l- phenyipropane accordiog to the balanced equation below. Br oCH3 : CefiSCHCHfiHa + ZCHBOH (34301.1 CaHsCHCH2CHa + CH3OH2‘” + Br’ The free energy diagram for this reaction is shown below. Q Q) C: m CU G.) M Lo ' {F'CHg C5H5CHBI‘CH2CK3 Cfii'IISCHCH'zG‘is + 2CH30H + (ii-130%“ + B!" Frogress of Reaction (A) (3) Define energy quantity A in like diagram. Tag-“L ”‘4‘"57 ° '9 “‘HVfiH m": b" Qfié‘c 4"ka V‘s—k Adm-Kflninj 911?} i (B) (3) Define energy quantity C in the diagram. 11M». (S‘M'vaar A) 4N4. Lew-4‘33 L‘Vmfimsx J (A 6(a).) (C) (3) Draw the key structure associated with the energy minimum B in the box in the diagram. (D) (3) Draw the key structure associated with enefgy minimum D in the box in the diagram. (E) (3) If (+)~1—bromo—1phenyipropane is reacted as above, what is the expected stereochemicai outcome in the product: retention, inversion, or racemization? Why? ranchizc‘cfiona 'biC-ngt "HM. rung-Hem. \mug\m$ cam-c reek”) Kim-UN hutJ-ieif‘k J Jr'kg Garbo cgj‘io'vv Chemistry 322aLx’325aL -9— Name Exam No. 3 (7) (5) (A) (3) Write a chemicai equation for the synthesis of ethyi neogentyl ether using oniy i reagents from the list of allowed materials below. Allowed Starting Materials 23% - . CH3SZCHZBr CHgCHgI . (EH3 CH3 —————————— . CHSCHzOCHZFCHg, - (gr-I3 CH3 CH3§CH2CY Na+ CH3CHZON¥ QA- Q‘JA‘ZS Q Q Q £ 3 CM “3% O Na. +— Ck—L 0+1”: ————--:-’ H3CH10Q423‘CH‘3 CH3“: 3 (B) (2) What is wrong with the other route? Thaw oflov mud-c... an“ M1— wop'c. Mg Hm~ $07— Maegsviom Vi. VLF-a fits“) WW ’hgcsgm—yq'nak SUSMS. m CH» @5169 (1 C5?) SLHLO a; 4r" Hr:3 (Gd-28¢ $9 (1145 JIM/0V" Wleé/I AmMfla Moo W ...
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