Solutions_Manual_for_Organic_Chemistry_6th_Ed 224

Solutions_Manual_for_Organic_Chemistry_6th_Ed 224 - 10- 19...

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Unformatted text preview: 10- 19 continued (b) � MgCl ( c) 10-20 (a) � HC gl + U U ?'"O 0 ---- H30+ + 0 ---- � OH H30+ � OH � � C: _ �D ( b) 10-2 1 There are more than one synthetic route to each structure; the ones shown here are representative. The new bonds formed are shown here in bold. Your answers may be different and still be correct. (a) � Br - ---- Li CuI (�C 2 � UL i � Br � (b) � Br ----- Li CuI ( �C 2 2 U Li (c) � Br ----- Li Cu A lternatively, coupli ng lithium dicyclohexy!cuprate with I-bromobutane would also work. As this mechanism i s not a typical S N 2, it i s not as susceptible to steric hindrance like acetylide ion substitution or a similar S N 2 reaction. (d) � Br ----- I (�C 2 ULi ( ()l U � ( � CJ" Li CuI 10-22 These reactions are acid-base reactions in which an acidic proton (or deuteron) is transferred to a b asic c arbon in either a Grignard reagent or an alkyllithium. ( a) (�C ( d) ULi CH3D Mg(OD)I + ( b) CH3CH2CH2CH3 LiOCH2CH3 0 CH3C-OLi + + o II 217 ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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