2_24_1997 - NAME(please PRINT Chemistry 1308 Exam ll...

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Unformatted text preview: NAME: (please PRINT) Chemistry 1308 Exam ll February 24, 1 997 0 Value Total Score 6 @ 5 each [email protected] (a) 10 (b) 15 (a) 12 (b) 5 (c) 9 (d) 4 I. Predict the major product(s) from each of the following reactions. Be sure to indicate stereochemisu'y where appropriate. l. 0”th ohm»; _—_____, mil 2. HanH Ph, arr. H* (a) (b) 0H 1. Newman, ”30”, )=o _________., "”H 2. HSM SH, MT 8% 3. Remy Ni “H (C) a 1 u. wanna 42‘ _______, 2. t'BwCHO , -?8' 3. NAH, Mcf’ 5 ° { NaUH , 910 CHO (d) |.(H‘LN)2« , cat. H” ——_—_____—__., 2. mm, HUNOV\0R am A (f) "K ., at ”1150*, 92.0 —__—_—__’ 0 o W Z'cm:Pfl’5’M II. Starting with alcohol 1, devise a short synthesis of ester 2 using any reagents of your choosing. 0 steps Y O“ 0 HI. The insect pheromone frontalin (3) derives from the intramolecular ketalization of a keto diol. (a) Give the structure of this immediate precursor 4 to 3, and (b) using a catalyst of your choosing, show mechanistically (i.e., arrow pushing) how frontalin is formed from 4. 4:57 - 4 (keto diol) IV. Below are the NMR and IR spectra for compound X, the structure for which is shown. "gaaegeusaauausfi 29°? IIIII M ”m m ”I, m “a m Im.§é§§ §_ Isis was”. he IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII*2; gee-34.4%; fifiggEE§§mggmmngnEtx IEIIIEII :1, “33:53:33: mfims‘g‘é afi‘fifififigfii‘? EEE§fifiwm ”‘5'”"“3’3§§§§§§3§§i§§§%§E2: =EEPan‘III manganese ‘gggfig ammnmm lgfllfi 'IIIIIIIIIIIg” 7° IziéagggIg-mm 43m mm; IIWIIIIE'WIIIN “-55.45%. “I Baa-{11554: m: "Iiiziiiitgfiiafliil' IIIIIi'iig6° ”'egzag ‘ h ' Hlmmmlm ml nuiiiiig” ”.322? ‘ flmfifil‘lfimdfllg? gagsgsg; g a, __ IIIIIlIilimiiiIIiiiiiilII II II. 43%” .‘ "I g £31mllIIIlhllll'llbdllidllmmlfiIIII :;.:—- i ' ..' 'lEI: . fimmlfi‘lfil‘l'fll’l" "ll’l 'llmlIllmllIH'“ 353:“. I IIIIIIIIIIIJIIEEEI‘ITIsIIIHIIIII"Iii: (1) Assign the signals in the proton NMR spectrum for compound X. (2) Sketch the proton-decoupled 13C NMR spectrum for compound X, being sure to indicate the approximate chemical shifts. (3) Label 3 of the peaks in the IR spectrum for compound X. (4) Give the IUPAC name for compound X. ...
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