Quiz_3_Key_Summer_2009

Quiz_3_Key_Summer_2009 - Kev ‘ Chem 308, Summer 2009 D...

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Unformatted text preview: Kev ‘ Chem 308, Summer 2009 D Quiz 3 Section H1 NAME . ‘ .‘ (3 pts.) Draw the structure of the major organic product of the reaction below. , l r \ CH3NH2. NaBHaCN, CH3OH‘ ‘ V ~ W ’P ‘ ‘ Qmmw'fi- ‘3 e reagents and reaction steps required for the synthesis shown below. ‘\L<,N ‘0? New —I. 2. (2 pts.) Give th O \ ~ QM’Q’SS HO‘ CN- )l\_ 2 . QM no MW: ‘ 3. (2 pts.) Draw a Fischer projection to represent the open-chain form 3‘. géf of the carbohydrate shown below. ' ’ ‘ Q i ‘ CHzOH “\é’b ' 0M3 M ‘ H 03A M i u 0 ll Ho ll H 0“ QHLOH a detailed mechanism for the conversion ShOWn below, showing all intermediate structures. Use 4. (3 pts.) Write ectron m0vement, and indicate all formal charges clearly. curved arrows to indiCate all el HO OCH3 . catalytic Her, CHSOH - H300 OCHs X M lug? 7L*¥\® V‘ r ‘ 4 ‘ El - 59‘ (0 09"; H36“ 0 H0 693 H§j<0fl4l3 ID Chem 308, Summer 2009 NAME ' ' Quiz 3 Section H2 2. (3 pts.) Give the reagents and reaction steps required for the synthesis shown below, which requires the use of a protecting group. 0% . Q ‘. GR C a 0 l.-H0/\/ )P‘ 1/5” “EL;- 3. (2 pts.) Draw the major organic productof the reaction shown below. - ‘ 9 ea. talc ' R O ' ‘ H2c:———-—PPh3 M/ /U\ . V ‘ i 7 .9 echanism for the conversion shown below, showing. all intermediate structures. Use ll electron movement, and indicate all formal charges clearly. HOH c - HOHZC 2 O OH 0 OCH3 I ' . catalytic HCl, H20 V a ' . HO 'OH HO OH 4. (3 pts.) Write a detailed m curved arrows to indicate a GA ...
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Quiz_3_Key_Summer_2009 - Kev ‘ Chem 308, Summer 2009 D...

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