215-216 HH W10-Quiz 6-key

215-216 HH W10-Quiz 6-key - O H O Mn O NaOH/H 2 O O H 1 2 O...

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Chem 215-216 HH W10 February 19, 2010 Quiz 6 (this quiz has two pages) Name:_______________________ Lab Section: Mon; Tue AM; Tue PM; Wed (circle one that applies); GSI _____________________ I. (6 points) Treatment of allyl alcohol ( 1 ) with MnO 2 in basic water results in the formation of acrolein ( 2 ). Provide in the box below a step-by-step mechanism for the formation of the aldehyde, 2 , using the curved-arrow convention. You may start from alkoxide 3 . II . (6 points) Intramolecular substitution reactions depend strongly on the stereochemical relationship between the reacting functional groups. Which one(s) of the following reactions can undergo intramolecular substitution to produce its (their) ether product(s)? Provide in each of the boxes below a drawing of 3D bridge structure of the product. If no intramolecular substitution is expected, write NR in the box and draw the 3D structure of the starting alcohol.
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Unformatted text preview: O H O Mn O NaOH/H 2 O O H 1 2 O 3 6 O Mn O O Mn O O H H HO OH H 2 + H 2 O + Mn O O O Mn O O H H O H 2 + Mn OH O or +4 +4 +2 need not to show mech. arrows: 1 pt mech. arrows: 2 pt interm. str.: 2 pt Mn (+2): 1 pt Br OH OH Br OH Br H H H Note: 3D bridge structure NaH NaH NaH (1) (2) (3) 2 2 2 Br OH OH Br H H O H NR NR Chem 215-216 HH W10 Quiz 6 page 2 III . (8 points) Complete each of the following reactions by drawing the structure of the expected major product in the box. Make sure to clearly indicate the stereochemistry whenever applicable. 2 O H 3 C D D 3 C H O H 3 C D D 3 C H 2 tetrahrdrofuran (solvent) 0 C, 1 h HClO 4-H 2 O CH 3 ONa-CH 3 OH reflux, 2 h 2 2 tetrahrdrofuran (solvent) 0 C, 1 h HClO 4-H 2 O H O tetrahrdrofuran (solvent) 0 C, 1 h HClO 4-H 2 O H O OH H 3 C D D 3 C H OH OH H 3 C D D 3 C H OCH 3 H HO HO H HO HO diaxial opening of the epoxide ring...
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This note was uploaded on 02/24/2010 for the course CHEM 215 taught by Professor Koreeda during the Spring '07 term at University of Michigan.

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215-216 HH W10-Quiz 6-key - O H O Mn O NaOH/H 2 O O H 1 2 O...

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