W09_215_E2_key-1 - Name_KEY W09_215_E2_p1 I(20 points A...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
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
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
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
Background image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 09/21/2011 for the course CHEM 215 taught by Professor Koreeda during the Winter '07 term at University of Michigan.

Page1 / 5

W09_215_E2_key-1 - Name_KEY W09_215_E2_p1 I(20 points A...

This preview shows document pages 1 - 3. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online