Solutions_Manual_for_Organic_Chemistry_6th_Ed 169

Solutions_Manual_for_Organic_Chemistry_6th_Ed 169 - 8 -8 HO...

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Unformatted text preview: 8 -8 HO (a) (d) (f':: " CH 3 (OAC) (b) H X CI (a) 8 -9 (b) (c) &, � � Hg(OAc}z CH30H O.- U OCH J (c) CI O OCH3 I : l II Hg(OAc) o. Hg(OAC) " OCH3 NaBH4 .- KOH,� .- Hg(OAc}z 6 H .. � OCH 3 .. Hg(OAc}z H2O N aB H 4 .- 8 -10 (a) , (b) B H3 0THF .. � B H2 � H202 OH Using an acid-catalyzed hydration In part (c) would initially form a 2° carbocation that would quickly rearrange to 3" on carbon-3. The desired product would not be synthesized. .- H O HOH2 02 � OH (c), (d ) � B H3 0T HF (e) , (f) 8 -11 (a) � � 6 BH3 0TH F C .. HaB: B H2 .- � , HO- .- H20 2 .- � OH C HO- HaO: ~ OH -----;.-� B H3 ° THF H202 HOHg(OAc}z H2 O .. HO� (b) NaBH 4 .. (c) � Br KOH,� .. � � OH B H3 ° THF .- H2 0 2 H O- .- 162 ...
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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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