Fall 2009 Test #3 key

Fall 2009 Test #3 key - Chemistry 322a,1“ 325a-2— Name...

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Unformatted text preview: Chemistry 322a ,1“ 325a -2— Name: Third Midterm Exam 1. (6 pt) In each pair of compounds, circle the stronger acid (2 pt each). 2 Pan #5 2. (6 pt) )For the indicated hydrogen atom estimate the water-referenced pKa (2 pt each. (cred-f OP(O)( O)(H) L) (“Gila-13x, in) I ® I five) I '5) Mg: gags- l-‘93 3‘) “73—0 fl)“: 5W (av?!— 3 (6 pt) In each pair of isomeric structures circle the one that 15 more stable, that IS, the one with the most negative heat of formation. In the event of a tie, circle both (2 pt each). .-f {7% apams atria—L5, 4.(6 pt) Estimate the TMS— referenced chemical shift (ppm in CDC13) for the indicated oton (TMS= SiMeq, 2 pt each). 61089- heck. .969- 05 -?7_ 26] 94,1 [it "3‘32, Chemistry 322a / 325a Third Midterm Exam -3— Name: 5. (14 pt) What integration and coupling pattern do you expect for the indicated proton(s)? Do not forget to count any equivalent protons that appear in the same signal. Answer DH, (s)inglet, (d)oub1et, (t)riplet, (q)uartet, (quin)tet, (dd)ouble doublet, or (m)ultiplet. Assume that the integrations are normalized accurately to count all of the hydrogens in the molecule (2 pt per box). Also, how many 13C signals (types of carbons) do you expect in the 13C NMR Spectra of these molecules (1 pt per box)? 6. (40 pt) Fill in the missing starting material, product, or reagent from the synthetic schemes below. Be sure to include any stereochemical details that you are able to describe. Although it is not important to indicate the inorganic side products, indicate all of the organic products. Where applicable, indicate whether there is a major product or if materials are formed in a 1:1 ratio (5 pt per box). O” % (at) (oumwm' CH2'2 MB ( i) A/O anCu 1 (3t £410 chew; (g) Cat/1146,57 ism—7 H2 (2.?) enema-mirth PdfC —" Chemistry 3223 i’ 3253 -4— Name: Third Midterm Exam 6. (40 pt, continued) H / mCPBA —_.. (excess) \Jv i. Hg(OAc)2, H20 / ii. NaBH4, NaOH —" (3) {pa-2902’s (2/) Swindle“ {2) 62,0624? H50 “5-: arm 6 l-vf : m (3) Comma-hurt? flH/i 1. mCPBA (+f-) Reju‘ml (2,) %}t€.-rcodCM-V\ ( [/ 2. H2304 (cat) (L) ’btuéée..13[ CWJFCC 1- Edi/LE. G_. (2.) 411 8/0 (L) 11/! L3 (21,.» C !‘--"6( A . AL. .\ - [ii (figzZGi [Zr-{SUCQLL If) wfi ( “(5(61' 43.! C ( Chemistry 322a I 325a -5— Name: Third Midterm Exam 7. (15 pt) A compound of formula CQHS has the 1H NMR and IR spectra below. Propose its structure. Partial credit will be given for partial structures, A/pt per correct spin system. g 3b Loco”g 3’ Degree of , L unsaturation 2H 2H ““7 1H m m I‘Cgl‘otl‘imfir' 100 El] 2U 3003 3000 2000 lSEIEI lflflfl 500 £100 Wavenumberlcrn- 1] Chemistry 3223 I 325a 6— Name: Third Midterm Exam NMR spectra below. Propose its 3 per correct Spin system. m 7* (o ”“9 (w m We ”(CW—5 Degree of unsaturation / H - m ppm 10 9 8 ? 6 5 4 3 2 1 0 ppm 180 160 140 120 100 80 60 4O 20 0 Chemistry 3223 I 325a -7- Name: Third Midterm Exam 9. (3 pt) Spirocyclic ketone C can be prepared in 2 easy steps from bicyclopentylidine (A). Predict the structure of synthetic intermediate B and propose a mechanism for the conversion of B to C. Be sure to show all bond forming and bond breaking steps separately. 020 i. 080. I ii. Naisos A T5 9/?! C47) ‘9 H 10 6 h \ V / 10. (9 pt) Propose a stereospecific synthesis of racernic diketones E from norbornene D. You can use any reagent you like, but Mel should be your only other carbon source. It is unnecessary to _ show mechanistic details. (J Paw-3'7 HF Br MeO m7_,/\, it H2937 @ D E (i) I .‘—-‘ \{H h x - “5:14.- 63 [:1 Ass (f) 3&3 7L (QM LA“; i"%% “OLA? you; M 11 T t h (,9 a V O L? —H fen P0 1% . _ 5‘ MK” ' /m “H 3 r’BLva OWL??? E0040 (“fit/9:31.11 mun] _ ("i-HA Mmrtcs (CO Facet/MEL ...
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