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Quiz2Fall2007

Course: MEDC 501, Fall 2008
School: VCU
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OF DEPARTMENT MEDICINAL CHEMISTRY SCHOOL OF PHARMACY Medicinal Chemistry I Dr. Umesh R. Desai MEDC 501 October 11, 2007 STUDENT NAME Ring Size Saturated Partly Saturated HONOR PLEDGE Unsaturated 3 4 5 6 7 8 -irane -etane -olane -inane -epane -ocane (dihydro) (dihydro) (di or tetrahydro) (di, tetra, or hexahydro) (di, tetra, or hexahydro) -irene -ete -ole -ine -epine -ocine 1. Write the systematic name for...

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OF DEPARTMENT MEDICINAL CHEMISTRY SCHOOL OF PHARMACY Medicinal Chemistry I Dr. Umesh R. Desai MEDC 501 October 11, 2007 STUDENT NAME Ring Size Saturated Partly Saturated HONOR PLEDGE Unsaturated 3 4 5 6 7 8 -irane -etane -olane -inane -epane -ocane (dihydro) (dihydro) (di or tetrahydro) (di, tetra, or hexahydro) (di, tetra, or hexahydro) -irene -ete -ole -ine -epine -ocine 1. Write the systematic name for the following heterocycles. O N CH3 ___________________________________________________________________________ H N _______________________________________________________________________________ Me O N 2. S Me ______________________________________________________________________________ Rank the following according to their stability to ring opening conditions, e.g., high temperature, strong acids, etc. Use 1 for least stable and 3 for most stable. NOTE: The entire sequence has to be correct, otherwise zero points. H N H H N N 3. Rank the following according to their stability to acidic conditions, e.g., H2O/H+. Use 1 for least stable and 3 for most stable. NOTE: The entire sequence has to be correct, otherwise zero points. O O OMe O OH 5. Whereas ________________________ isomers can be obtained by mere rotation around single bonds, to interconvert ________________________ isomers one has break bonds. 4. DEPARTMENT OF MEDICINAL CHEMISTRY SCHOOL OF PHARMACY Draw the structure of products formed in the following reactions. If no product is formed, write none. O HN MeS Hydrolytic Enzyme pH 7.2 - 7.4 _____________________________________________________________ O H3C Et pH 7.2 - 7.4 Epoxide Hydrolase ______________________________________________________________ 6. Following is a chair form of a monosaccharide. Draw its conformational that isomer might exist in equilibrium. Circle the conformation that is expected to be more stable. Justify your choice in not more than 2 or 3 sentences. HOCH2 HO OH O OH OH ___________________________________________________________________________________ ___________________________________________________________________________________ ___________________________________________________________________________________ ___________________________________________________________________________________ ___________________________________________________________________________________ ___________________________________________________________________________________ ___________________________________________________________________________________ 7. For the structure below, draw the appropriate tautomer that may exist in equilibrium. What is this tautomerism called? OH N N OH 8. Circle each chiral center in the following molecule. Please mark each center clearly and distinctly. H3C CH3 H3C CH3 H3C HO N H N DEPARTMENT OF MEDICINAL CHEMISTRY SCHOOL OF PHARMACY 9. What is the Cahn-Ingold-Prelog identification (the R or S form) of the following stereoisomer? NH2 H3C Ph H 10. Clearly define the following terms in not more than 2 to 3 sentences. Enantiomers : _____________________________________________________________________ _________________________________________________________________________________ _________________________________________________________________________________ Diastereomers: ____________________________________________________________________ _________________________________________________________________________________ _________________________________________________________________________________
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