Solutions_Manual_for_Organic_Chemistry_6th_Ed 308

Solutions_Manual_for_Organic_Chemistry_6th_Ed 308 - 1 4-8...

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Unformatted text preview: 1 4-8 SN2 reactions, including the Williamson ether synthesis , work best when the nucleophile attacks a 1 ° or methyl c arbon . I nstead of attempting to form the bond from oxygen to the 2° c arbon on the ring, form the bond from oxygen to the 1 ° carbon of the butyl group. The O H m ust first be transformed into a good leaving group: either a tosyl ate, or one of the hal ides (not fluoride). T sCI � OH p yridine .. � OTs 1 4-9 (a) Q �Q (f A OH 0H Na ... OH 0- Na+ � OTs .. CH3CH2CH2Br .. ( b) Na ... CH3I .. ( c) (d) CH3CH2CH20H CH3CH20H CH3 I CH 3-C- OH I CH3 (1) � or ¢ OH A Na OH ... CH3I .. N0 2 Na Na ... ¢Hl OCH3 N0 2 ... (f 0� Q O� 3-butoxy-l,ldi methy Icyclohex:me CH3CH2Br � CH3CH2CH2Br PhCH2Br --_.. CH3CH2CH20CH2CH3 ... CH3CH 2CH20CH2CH3 ( e) Na • CH3 C - OCH2Ph CH 3 I CH3 OCH3 1 4- 1 0 ( a) H g(OAc)2 � ( 2) C H30H • NaBH � � OH � Na ... CH31 ... � 30 1 OCH3 ...
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