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Solutions_Manual_for_Organic_Chemistry_6th_Ed 206

Solutions_Manual_for_Organic_Chemistry_6th_Ed 206 - 9-20(a...

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9-20 (a) But-2-yne is symmetric. Either orientation produces the same product. ° Sia2BH CH 3 CH3 \ / H202 CH3 CH3 \ / HO- II CH3-C C-CH3 .. C=C .. / \ HO- C=C / \ -- -I"� CH3CHz - C - CH3 H BSia2 H OH (b) Pent-2-yne is not symmetric. Different orientations of attack will lead to different products on any unsymmetrical internal alkyne. CH3 -C C -CH2CH3 �H S CH3 CH2CH3 \ / C=C / \ H BSiaz H202 , HO- CH3
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