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midterm2answer - lE'Jhemistry1-flllllr1ll NAME: {please...

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Unformatted text preview: lE'Jhemistry1-flllllr1ll NAME: {please print} AHSW Professor Jerry Yang First Last sous, Examination #2 May 15, 20:15 Signature: PID #: WRITE YOUR NAME AT THE TOP OF EVERY PAGE! Write the name of the person sitting: To your right To your left Please check your section number: A1 M BFB:5DAM AB F 1242:5DPM A2 F B-B:5DAM A? F 1-1:5DPM A3 M tfl-‘tDfiflAM A3 F 2-2:5DPM A4 M 11-11:5EIAM A9 F 3-3:5flPM A5 M 12-12:5E|FM A1fl M 2-2:5flP|'H'| Other {please explain}: DO NOT OPEN YOUR EXAM UNTIL YOU ARE TOLD. Please write the answers you want graded in the space provided. Do scratch work on the backs of the pages. The test should have ? numbered pages. Check to make sure you hays received a complete exam. A good piece of advice: Flead carefully over the questions at least twice; Make sure that you understand exactly what is being asked; aycid sloppy structures or writing. Geog Luck! DO NOT WFiiTE BELOW THIS LINE 1. {12} ll. {24) III. {e} w. {20} y. (as) VI. to} VII. {s} Total [1 DU} i. [12 points] NAM E: [please print} First Last Home or draw, as appropriate, the following moleoules. Please write your answers in the space provided. Indioete stereoohemistry where necessary {l.e., ois, trans, Ft, 5}. You may use condensed notation, or line diagrams tor your drawings. NO FISCHER PROJECTIONS! Provide Home of structure: CH3 it}: s jfi'cflimoflmfi [38]-1,1,3-trimethy1 oyolope ntane Two chiral isomers of diohlorooy clobutaoo ||. [24 points] NAME: {please print] First Last Hydrogen peroxide converts alkanes to alcohols under tree radical conditions with HD- as a chain carrier. For example: hv CH4 ‘i' —'*" '1' H20 a. 2-methylhutane reacts with HDDH under free radical conditions to give ONLY SIX alcohol products: 2 achiral isomers, and 2 pairs of enantiomers. Draw ALL six possible alcohol products tor the reaction in the spaces provided. Make sure 1grou specify the stereochemistry. ND FISCHER PROJECTIONS! 2 achfial pmduds 1 pa1r of cnantiomsrlc Omar pair of products enantiomcric products ,oH _ A/xw L/ /L{H Q n h. The selectivity of HD- in attacking C-H bonds ls 1°:2°:3° = 1:55:35flfl. For the reaction: h .l (CH3)3CH + HUGH —‘—-— {engscoa + (GHQQCHCHEUH + H20 What is the expected ratio of the observed alcohol products? {Show your work} .- tetra of Ir” 11W 5": (15‘3" HflGeiedi‘wtg ci 5’} = (1163de 5mg (CHSECDH I (CH3}2CHCH:DH = 00 3 ct Ill. [El points] NAME: {please print] First Last Using the following table: Difference in energy between axial and equatorlal substltuted cyclonexanes {kcal mol“) Substituth oH m a; Substituent ail-i mm H o F 0.25 CH3 1.? CI {3.52 CH3CH2 BIT [GH3}2CH 2.2 I 43.46 [CHEJHC s OH {1.94 CH3'D 0.?5 CDDH 1.41 HEN 1.4 CDDMe 1.29 3. Draw the most stable chair conformation for the following molecule {use the templates provided]: ' (You may omit the H's on Us 3 through 5) b. How many stereocenters are there in molecule X? # storcooenters 01 in X c. is X an achiral, chiral. or meso compound? chum sx 4 IV. [20 points] NAIL-1E: {please print} First Last For each ot the totiowing pairs of structures, first give the relationship between the two {i.e., are they the same compounds, enantr‘omers, drsstereomers, conformers, or constitutional isomers). Then answer the second question. Please put your answer in the space provided. a. ' ' . . HO h ReEattonship of structures: 5cm mmpmwefl s“ _ ~‘ R Is the structure on the right H COEH o ticallv acti‘t-‘efJ h. Relationship of structures: F CI 15 the structure on the right cl F chiral cr achiraI'? [ Relationship of structu res: I" J" I . giigi'drecm What is the stereocherrtistrjr (R or S) at carbon: 1 2 3 R V. [20 points] NAME: {please print} First Last Write the major product ct each of the following reactions (“no reaction” is a possible answer} NO FISCHER PROJECTIONS. You should ignore In your answer any.»r salt products formed in the reactions: M/ Br c: + HOW SH + T Ho cc?r N? 1 mole equivalent of 9 EB CH O N arse/VOW} 3 a —...._ 1 mole equivalent of CH3—l 1 mole equivalent of NaCN —'-i_ Nb 1 mole equivalent of 6% HDK 1 mole equivalan of S 6 HO Na a sulfide VI. [9 points] NAME: {please print} FifST. LBST. For the following pairs of reactions, mark an “X” in the box on the right indicating which will go faster. The compound on top of the arrow is the solvent. o El. NO” + Lic1 we N?" + LiClTs ‘ CH3DH NOTE + LiCi —~—:-— N“ + LiOTs h. &\ cnqon &\ ' E + MESH __y..* SH + NaI + 5351.1 —p-.-“ SH + NaI “x CI- II ’5‘“ E a cmso ocH .\/ r+ sacrum3 ( } V 3 + “1313‘ VII. [5 points] Clearly: list ALL of the stereccentera in the following structure of daunomycin, a potent anticancer agent: 0 cm 0 List of all stereo-centers (Lg, a,h,etc.}: ...
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midterm2answer - lE'Jhemistry1-flllllr1ll NAME: {please...

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