Unformatted text preview: 1 Spring 2006, CEM252 Exam 3 (100 Points) 1. (6 Points, 2 points each box) Give the correct structures for the following compounds.
a) L-Methionine b) Benzyl Phenyl ketone c) D-2-deoxyribose 2. (6 Points, 2 point each) Give the proper systematic or common name for each of the following compounds.
N CHO H HO OH H OH OH CH2OH b) H H H c) PhCH2NCH2Ph 2 3. (4 Points) Encircle the strongest base among the following amines.
N Cl H N N H N (CH3CH2)2NH F Cl A B C E 4. (5 Points) Draw the structure of the a-pyranose (Haworth formula) for the following sugar.
CHO H H H HO OH OH OH H CH2OH a-Pyranose Form 5. (5 Points) Encircle all reducing sugars among the following. Please note that any wrong answer will cancel one right one.
CH2OH OH OH O OH H H OH OH OH OH HO O CH2 O O OCH3 H A B OH CH2OH C HO OH HO CH2OH HO O CH2OH O OH CH3 HO OH C D 3 6. (6 Points, 2 points each box) Complete the following polymerization reactions. a) F2C CF2 ROOR Heat A short segment of the polymer O NH H3O , Heat b) Heat A short segment of the polymer 7. (8 Points, 2 points each box) Indicate whether each of the following reactions is an oxidation reaction, reduction reaction, or neither.
Lindlar's Catalyst A) H3CC
CCH3 B) CH3CH2CH2OH H2CrO4 CH3CH2CH2CO2H Swern Reagent C) CH3CH2CH2OH CH3CH2CH2CHO D) HI I 4 8. (4 Points) Draw the structure of L-valine in a 10 percent sodium hydroxide solution (PH = 13). 9. (4 points) Identify the alkene that would give the following products upon ozonolysis followed by treatment with zinc/water. O 1) O3 2) Zn, H2O O O O + 10. (6 point) Outline an efficient synthesis for the following dipeptide starting with amino acids and any other necessary reagents. CH3 O
H2N CH2Ph N H CO2H 5 11. (20 Points, 5 points each) provide an efficient synthesis for the following compounds starting with the given starting material and any necessary reagents.
H3CC CCH3 CH2NH2 B) Br ?
CO2H C) Br ? D) CO2H ? OH 7 8. (26 Points, 2 points each box) Complete the following reactions by filling the boxes with the appropriate reagents, reactant(s), or product(s). For the products, only include the major organic products. O 1) KOH a)
NH O 2) PhCH2CH2Br 3) H3O , Heat + Show both of the products
H2N b) 1) Excess CH3I 2) Ag2O, H2O, Heat c) PhCH2CHO 1) NH3, H 2) NaCN, HCl 3) H3O , Heat 8 O OH OH d) CHO H OH H OH OH CH2OH e) HO H H Ag2O, NH4OH (Tollens Reagent) f)
HO HO H OH H O CH3OH, H
H H H OH OH Draw b-glycoside CHO HO H OH OH CH2OH 1) NaCN, HCl 2) H2, Pd, BaSO4 3) H3O g)
H H 9 h) H N O 1) LiAlH4 2) H2O i) 1) OsO4 2) H2O2 CH2OH O j) HO HO OH H OH Ag2O NH4OH (Tollens) k)
N FeBr3, Br2 300 o C ...
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This note was uploaded on 07/25/2008 for the course CEM 252 taught by Professor Rathke during the Summer '08 term at Michigan State University.
- Summer '08