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040128-key - NAME Kgy(please PRINT Chemistry 1 093 Exam I Q...

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Unformatted text preview: NAME: Kgy (please PRINT) Chemistry 1 093 Exam I January 28, 2004 Q Value Total Score 1x10 1x10 3+6+8+9+4 1. Provide the major organic product(s) from the following transformations. Be sure to include stereochemical information where appropriate. (6) 1. Lindlar reduction ——-———-—-——> 2. dichloroCarbene 1. K+ 'O-t-Bu -——————————-———-> 2. MCPBA NaNH2 THF, A 1. Na / liquid NH3 —-——————-——> 2. BIZ 1.HBr ——-—-——_—> 2. Mg 3. D20 Cl "I“ (,1 + .m‘ ? tn“ 9" ‘ s v 3 0 II. When alkyne 1 is treated under the following reaction conditions, essentially no reaction occurs (i.e., starting material is recovered). Why? Provide a brief explanation, and a solution (without changing the starting material) such that the reaction will take place and go to completion. Et W 1. n-BuLi, EtOH, 0° x , W 2. Et-I ’lhc 1 ba« n’BwLi, wauld immdmi‘ Moor win. 01!: salt/Mr. WH W m Lioévr whim is nof 5W emu h '17 u” 07! all M Mm. fimakflvm dram ’ lmW/TMJA’WFN mm 4pm salt/m). 3. Draw a 3-D picture for the most stable vinyl anion intermediate in the reduction of 2-butyne with sodium in liquid ammonia. 4. Hydroboration of the alkene 2 below can be effected to give an intermediate X Which reacts further to give isomerically pure product Y, an alcohol. hydroboration V reagents —————> 1,, H 3B '0, 0” (21) Provide the name for the starting olefin 2. |—~ cyctohcxyl oyoto hex an e (b) Give the reagent(s) to be used for effecting these transformations (2 to X, and X to Y). [2 to X] Bits (or 6W) [X to Y] #07 HM? (c) Provide structures for X and Y (in the boxes). (d) Suggest a mechanism for converting 2 to product Y via X. “"3 600” [l ' '9 $1 ’ ”I, I ' "‘7 9/ 0 0“ ‘L ‘ / [’1’ B\ l' B K RH" K H L H20 Ht?9 . h— ”/OH Quay Hvo '_ ””038: 6" Y (e) If Y is exposed to PCC, suggest the structure for product Z (in the box). ...
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