A provide a brief explanation as to how the

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reaction. (a) Provide a brief explanation as to how the hydrophobic effect could influence the reaction rate between these molecules. (b) Provide a drawing of the two molecules plus some water molecules that illustrate your explanation. NH 2 B r O O N O O H H explanation drawing B . When treated with mild acid, Compound A is isomerized to Compound B . Provide a complete, step-wise mechanism for this isomerization. Y ou may use H-B for your acid and B for its conjugate base. O H OH H 3 C H 3 C OH O H 3 C H 3 C H HB Compound A Compound B Compound B is the more stable isomer. Why? O H OH H 3 C H 3 C OH O H 3 C H 3 C H 14 4 4 4
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Name _______________________ Page 4 F.08.215e3p4 I V . ( 19 points) Complete the following reaction schemes. (a) JOC 2007 72 9541 O O O O O O OCH 3 O O O O O O O O Br O OCH 3 O O O O O O excess N O O L i (b) D -Glu excess CH 3 CH 2 OH cat H 2 SO 4 Show the Fischer projection of the product at low pH (c) 4 3 4 4 4 O N(CH 2 CH 3 ) 2 N OH HO H O H Draw the open chain Fischer projection for this carbohydrate derivative, which is in its cyclic hemi- acetal form. Note: open chain form... not the modifed Fischer projection for the hemi-acetal.
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Name _______________________ Page 5 F.08.215e3p5 V . (20 points) At what pH value are 100% of the molecules of this amino acid in this specific structure? (a) H H 2 N N NH 2 NH 2 H O O (b) Draw the amide resulting from the reaction between propanoyl chloride and L -valine (use a Fischer projection and assume a low pH condition). (c) Draw the Fischer projection for a D -aldopentose that would give an optically active product after reduction with NaB H 4 . (d) NH N N O NH 2 N O OH OH H H H H HO H 2 O mild acid catalyst (e) 8.0 7.0 9.0 This is a portion of the titration curve for which amino acid? Give the three-letter abbreviation. 4 4 4 4 4 pH
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