Solutions_Manual_for_Organic_Chemistry_6th_Ed 207

Solutions_Manual_for_Organic_Chemistry_6th_Ed 207 - 9-22(a...

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Unformatted text preview: 9 -22 (a) CH3 H I I ----1.. 1 H -C-C-BH) I I CH3 CH3 H + \ H3C / C==C \ / CH3 CH3 CH3 H H H CH3 I I I I I H-C-C-B-C-C- H I I I I CH3 CH3 CH3 CH3 disiamylborane, Sia2BH (b) There is too much steric hindrance in Sia2BH for the third B-H to add across another alkene. The reagent can add to alkynes because alkynes are linear and attack is not hindered by bulky substituents. 9-23 (a) (1) HO-C-C-(CH2hCH3 oxidation of a tenninal alkyne with neutral KMn04 produces the ketone and carboxylic acid without cleaving the carbon-carbon bond o0 II II - C-C - CH2CH2CH3 ( b) (1) CH3 (c) (1) CH3CH2-C-C-CH2CH3 (d) (1) CH3CH-C-C-CH2CH3 1 CH3 (e) ( 1) o 11 o II 0 II ( 2) CO 2 + HO-C -(CH2hCH3 oxidation of a tenninal alkyne with wann, basic KMn04 cleaves the carbon-carbon bond, producing the carboxylic acid and carbon dioxide CH3 - C-O H + HO -C-CH2CH2CH3 o II o II ( 2) o II 0 II o II 0 II ( 2) CH3CH2-C-O H CH3CH-C-O H + H O -C -CH2CH3 1 CH3 o o II 0 II 0 II (2 ) (2) HO o OH 9-24 (a) CH3 -C:::C- (CH2)4 -C:::C-CH3 200 ...
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