W09_215_E2_key-1 - Name:_KEY_ _ W09_215_E2_p1 I. (20...

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I. (20 points) Name:_________KEY_________________ ____ W09_215_E2_p1 A) Provide the products or reagents necessary to complete the following reactions. -For products: draw the stereostructure of the major isomer as appropriate. -For reagents: number steps if more than one reaction step is required; if more than one equivalent of a reagent is necessary, indicate this using the word "excess". i) O + O H (excess) NaOH H 2 O C 17 H 14 O ii) CH 3 O OH CH 3 O N iii) O O H 1) excess CH 3 MgBr 2) NH 4 + Cl - iv) O O + v) O D 2 O N(CH 2 CH 3 ) 3 Molecular weight = 102 Molecular weight = 98 O E isomer major product 1) SOCl 2 or PCl 3 2) excess N H In step 1, could also make anhydride (heat) or ester (TsOH, HOCH 3 ) In step 2, could use 1 eq of amine and an equivalent of pyridine or TEA (N(CH 2 CH 3 ) 3 ); in step 2 with ester, only need 1 eq amine OH HO H H 3 C CH 3 1) could use excess CH 3 Li 2) could use H 3 O + O OH O H 3 C O D D D D 3 4 4 6 3 1) NaOH 2) NH 4 Cl could have carboxlate
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II. (21 points) Name:___________KEY___________________ W09_215_E2_p2 A) Cyanidin is a glucose-bound anthrocyanin responsible for the color of purple potato, red cabbage, and dark berries. Its color varies with pH. Cyanidin has four phenolic O-H bonds. Three of the four could be deprotonated to yield a conjugate base of cyanidin with a closed-shell resonance structure with no formal charge on any atoms. One cannot. O HO OH O Sugar OH OH O HO OH O Sugar OH O B) JOC , 2009 , 74 , 810. Below is a pair of molecules with their pK a s in DMSO. Explain the differences in pK a for each pair. Use words and structures as necessary. C) For each of the following molecules, circle the proton that will be removed when the molecule is treated with one
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W09_215_E2_key-1 - Name:_KEY_ _ W09_215_E2_p1 I. (20...

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