F.08.215.FEK - Name _______________________ Page 1...

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Unformatted text preview: Name _______________________ Page 1 F.08.215FEP1 I. (42 points) A. Provide the step-wise, curved arrow mechanism for the following ( OL 2007 , 9 , 385). OCH 3 H 3 CO O Cl OCH 3 H 3 CO O O OCH 3 O OCH 3 O H 3 CO O OCH 3 Na B. Provide the step-wise, curved arrow mechanism for the following ( JACS 2002 , 124 , 11975). CH 3 (CH 2 ) 14 C O OH + CH 3 (CH 2 ) 14 OH CH 3 (CH 2 ) 14 C O O(CH 2 ) 14 CH 3 H-B acid catalyst 9 33 + H 2 O OCH 3 H 3 CO O Cl O H 3 CO O OCH 3 Na OCH 3 H 3 CO O Cl O H 3 CO O OCH 3 OCH 3 H 3 CO O O OCH 3 O OCH 3 ADDITION = 3 tetrahedral int = 3 ELIMINATION = 3 CH 3 (CH 2 ) 14 C O OH H B CH 3 (CH 2 ) 14 C O OH H CH 3 (CH 2 ) 14 C O OH H H O (CH 2 ) 14 CH 3 H O (CH 2 ) 14 CH 3 B: CH 3 (CH 2 ) 14 C O OH H O (CH 2 ) 14 CH 3 H B CH 3 (CH 2 ) 14 C O OH 2 H O (CH 2 ) 14 CH 3 CH 3 (CH 2 ) 14 C O O(CH 2 ) 14 CH 3 H CH 3 (CH 2 ) 14 C O O(CH 2 ) 14 CH 3 B: PROTONATION = 3 protonated C=O = 3 ADDITION = 3 oxonium on HOR = 3 DEPROTONATION = 3 tetrahedral intermediate = 3 PROTONATION = 3 oxonium of HOH = 3 ELIMINATION OF HOH = 3 protonated C=O = 3 DEPROTONATION = 3 NOTES: (1) this must be shown as a simple basic mechanism; there is no acid present, so showing the acid-catalyzed mechanism is incorrect (2) the resonance form for the enolate with C- is OK (3) if this is shown as an S N 2 reaction instead of an acylation, then 3/9; no credit for the S N 1 mechanism (ie, carbocation formation) NOTES: (1) this must be the acid-catalyzed acylation mechanism; protonation of the C=O must be first (2) protonation of the OH followed by a bunch of S N 2 reactions is incorrect Name _______________________ Page 2 F.08.215FEP2 II. (39 points) Isomaltose is a disaccharide found in beer, honey, and other natural products. The IUPAC name for isomaltose is -D-glucopyranosyl-(1->6)- -D-glucopyranose. A. Complete the following as required ( JOC 2007 , 72 , 4953). B. O H CH 3 O O C (H 3 C) 3 C C(CH 3 ) 3 1) CH 3 CH 2 MgBr 2) H 3 O + protonation draw one of the product stereoisomers provide oxidation reaction conditons that will not interfere with the ketal The following reaction is observed to give a mixture of aldol reaction stereoisomers. Draw one of them ( OL 2007 , 9 , 421). C. N O (H 3 C) 3 CO H O OCH 3 H O CH 3 + BCl 3 D. Name this: CH 3 (CH 2 ) 14 C O O(CH 2 ) 14 CH 3 6 6 6 6 8 7 (catalyst) O O O OH HO HO OH HO HO OH OH-2 per error in structure; eg, alpha/beta, stereo, connection OH CH 3 CH 2 CH 3 O O C (H 3 C) 3 C C(CH 3 ) 3 OH CH 3 CH 2 PDC CrO 3 py PCC Swern (just name not OK) 1) (ClCO) 2 /(CH 3 ) 2 S=O 2) (CH 3 CH 2 ) 3 N connectivity = 3 stereochem = 3 full credit writing "Swern" = 2 Cr VI in acid are not OK O CH 3 CH 2 CH 3 O O C (H 3 C) 3 C C(CH 3 ) 3 connectivity = 3...
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F.08.215.FEK - Name _______________________ Page 1...

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