3_17_97 - NAME: (please PRINT) Chemistry 1303 Final Exam...

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Unformatted text preview: NAME: (please PRINT) Chemistry 1303 Final Exam March 17, 1997 0 Value Total Score 10@6each 60 20 25 55 40 200 1 . From each of the following, predict the major organic product(s). Be sure to indicate stereochemistry where appropriate. (a) cat (’60; H - m Br‘z , A H H a (b) *KO/0\ H ‘\H ‘aH ° Cfizaz MB (9) 1. M30, 5110 ——> 2 002 €S/\ Br 3 H319“ M0 an L H30? 2. HS/VSH, mteFa (e) I. 500% lazuli 2 CH1N2, E+zo _.'——-——* on 3. LOP! , m, "an" +_ (imam w New /\“/\/\ 0,0 M, Hw, A (g) H KDH, 02.0 \‘0 -—-—-——> H mm Twp. ('1) I. Na, I4. NH? OA‘\\\/k 2' 03 3. WPS i. was n-Buiis “OH —-——> W m, a 2. WM workup i. Milo; m 2. Hum, m. w (i) (i) ON 2.- Starting with acid 1 and using any reagents of your choosing, suggest a short synthesis of product 2 below. steps BLVCOOH -————> O 1 2 3 . When racemic acid 3 is treated with a catalytic amount of acid ‘TsOH’, a new product 4 is formed which shows an IR band in the 1735 cm‘1 range. 0 W cat TsOH —_> HO OH CH2C12 3 (a) Give the structure of product 4 (in the box provided). (b) Assign the IR band observed for this product. (c) Provide the IUPAC name for 3. (d) Give the structure for ‘TsOH’. (e) Provide a mechanism for the conversion of 3 to 4. (b) IR band at ca. 1735 cm‘1 is due to: (c) The IUPAC name for 3 is: (d) The structure for ‘TsOH': (e) Mechanism: 4. Ketone 5 undergoes a series of reactions, shown below, leading to products 6-14. Zn r—OH HCI 1. kinetic base cat H+ OH A 2 CH CH0 0 ' 3 1 eq Bra O/\)’\ 1. aBrz, x's aq KOH ‘—-— —————————> cat H2304 2. H30+ 5 2. NaH, Et-l MCPBA' CH20'2 2. AgNo3 , Br2 ‘—-— (a) Give the structure of a ‘kinetic’ base likely to be used to convert 5 to 8. (b) In the boxes provided, indicate the structures for compounds 6-14. (0) Provide a mechanism for the conversion of 5 to 8. (d) What is the pKa for the most acidic proton in 5? (indicate the proton, too); pKa = (e) The conversions of 5 to 8, 5 to 11, and 5 to 13 involve ‘name’ reactions. What are these? 1. NaBH4 l 1. NaOH 5 to 8: 5 to 1 1: 5 to 13: (f) Compound 14 is readily (i.e., in one step) converted to 13. Give the reagent for this trans- formation (under the arrow). (9) Suppose the base used for converting 5 to 8 was changed from a ‘kinetic base’ to aqueous KOH. Briefly explain what impact, if any, there would be on this reaction. 5. Compound 'X' gives the following IR, NMR, and MS data: MS: m/e (relative intensity) 118 (M+, 15), 103 (45), 101(18). 73(54), 59(100). m 625 we ran ' =gé " '° _~ _ ggg§=5=§§s§§§e§ '° .0 EEEE§EE§E§E§§§§32§§€§§E§E . .0 agg‘assszfi-agggggeggssssggs :V Eégagggg’éfiazsg _ J: 2%! ’° ,0 migasawsggg— é§gg==§ a a, ,0 gfifigmsfigafié . ,0 swaggsagas‘égagsgsg ea: :0! .0 salazfiigsgggsgzégggg $§§=él “ wages-$2352 as: s Eigggg — 3° A . , E igagagai 30 553215 ’° Egg; ’° E52?! 0 O l l ..........., l l r . ‘ . .s. I . ....f..-.. . s v ' ..-. n»... ........ ....._t...t .p- . . i l ‘ l. « 1' u l TWMINII ll 4 3 r l (3) Label at least 3 characteristic peaks in the IR spectrum. (b) From ALL of the data given, suggest a structure for 'X'. (c) Give the structures and charges for the five peaks observed in the MS of 'X'. ((1) Name compound 'X' using both IUPAC and common nomenclature. ...
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This note was uploaded on 02/01/2011 for the course CHEM 109B taught by Professor Aue during the Winter '08 term at UCSB.

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3_17_97 - NAME: (please PRINT) Chemistry 1303 Final Exam...

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