Solutions_Manual_for_Organic_Chemistry_6th_Ed 261

Solutions_Manual_for_Organic_Chemistry_6th_Ed 261 - 1 1-56...

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Unformatted text preview: 1 1 -56 cont nued i (f) HO � P B r3 .. Mg e the r (g) V � HO " H OH P CC.. T sC I .. S" p yr d ne T O ii H �o H .. Br g M� � K CN .. ' H NC o .. O0 S4 - Br 2 h v 6 Br � - Mg ether PCC C 3CH r H 2B P B r3 C H 3CH 20H t I I -57 F or a compl cated synthes s i ke this, beg n by wor in backwa ds. T y to fi gu e out where the i il i kg r r r ; i r carbon framework came from in th s problem we are restricted to alcohols containing five o fewer carbons. The dashed boxes show the fragments that must be assembled. The most practical way of form ng ca bon- carbon bondsi s by G r gnard react ons. The epoxide must be f ormed from an alkene, an i r i i d the alkene must have come fromd ehydration of an alcohol produced in a Gri gnard reaction. �o�<> ,,l, ,H ma or j i somer 1. 2. ° BfM g �. y ) Mg e the r t H 30: T sCl, p KO H ,1\ � 254 a void c arbocation conditions to prevent rearrangement !W 0: Mg r B \ cr 03 , H 0 acet ne 2S 4, o 2. Mg L� o- 0H ...
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