Solutions_Manual_for_Organic_Chemistry_6th_Ed 251

Solutions_Manual_for_Organic_Chemistry_6th_Ed 251 - 11-36 1...

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Unformatted text preview: 11-36 1 1-37 ( a) ( d) OH o-� + CH/�"'0-S03CH3 ---o-� OCH3 :0-S03CH3 SOCI2• CH3CH2-C-CI HC30H3+ CH2MgBr CH3CH2-CCH2CH3CH3 -CH2 CH3CH2-C-OH OHS04 2 BHH30•2, HO- � HCH2CH3 CH2CH3 2 CH3CH C-CH2CH3 CH3CHCHCH2CH3 OH OH cr0304• � b) CH3CH2CH20H PCC CH3CH2-C-H CHH30C+ H2MgBr.. � H2S ( 3 (alo- 0H H+ HC03H OH o H30+ U 'OH H30+ Q--\ OH HCI CI (blo- 0H cr03 O Q--\ HBr23SO: MCg,H3CH2MgBr'" CH3CH20H P CH3CH2Br OH �� Mg � U O Ho+ � H+ � Br MgBr 3 HT � r03 H2S OR: c0H �04o- Br Mg -- .. H,o+ Q-f; 0H��! ���A ) orn 0 ) - �gBr O-(;;C o- 0H � O- Br ��. 0 CH3Br HJ Q-f; CH30H �r3 o-� � 0: N a + .. � " o II + ° II 1) 2 2) • I I I I 1) TIIP 2) ..I---..... - = I ---- ° II 1) ° 2) a cetone 11-38 --f!. • " an pero acid canb e usedt o f Olm t he y xy epo ide wh ch is c l eaved to the trans­ x i di l in aqueous acid a _ --- � U ___ � /' e ther (c) --- � ether from Dart (b ) ----'� - .. --- --­ � ether � _ from (c) see the ne t pa efo an al te at ve end n xgr rn i ig 244 e ther ...
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