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Chemistry 11 Fall 2013 Examination #3 PRACTICE TEST1 ANSWER KEY 1. Consider the structure of a derivative of N-demethylglycopyrrolate shown below, a drug that reduces the production of saliva in patients that suffer from excessive drooling: N-demethylglycopyrrolate derivative H OH N O O O O N A. Identify the SIX functional groups present (exclude the benzene ring). 1) 2) 3) alcohol ester amine 4) amide 5) alkene 6) ether B. Determine the molecular formula of N-demethylglycopyrrolate. C22H30N2O5 C. Circle one answer in each row that so that your response best describes the OC=O bond angle in N-demethylglycopyrrolate. Trigonal planar 45 60 tetrahedral 90 trigonal pyramidal 109.5 linear 120 Now circle the phrase(s) below that correctly describe(s) Ndemethylglycopyrrolate. optically active optically inactive 1 chiral achiral aromatic bent 180 D. H OH N O O O O N Add, subtract, or otherwise change NO MORE THAN 3 ATOMS (in the above structure) to create a new molecule that contains a ketone as a functional group. Answer: Lots of possibilities here. Can change amide group to a ketone. Can change tertiary amine to a ketone. 2. A. Clearly label all the stereocenters in the structure shown below, labeling each one as either R or S. O N O R B. R How many diastereomers are possible for N-demethylglycopyrrolate? 2 How many enantiomers are possible for N-demethylglycopyrrolate? 1 Draw one enantiomer and one diastereomer of N-demethylglycopyrrolate in the box below (if they exist; otherwise, write NOT POSSIBLE and briefly explain): 2 H H O O N N O O ENANTIOMER 3. DIASTEREOMER In pharmaceutical chemistry, molecules with similar structures will often be synthesized in attempt to find more effective drugs or to eliminate unwanted side effects. Drawn below is a structural analog of N-demethylglycopyrrolate, called Molecule A. Molecule A OH O CH3 RO CH3 = O NH2 NH2 CH3 CH3 Draw the most stable and least stable chair conformations of Molecule A. (Hint: you may wish to abbreviate a portion of Molecule A as an "R" group for simplicity, but you must clearly identify your abbreviation.) CH3 CH3 RO CH3 CH3 OR NH2 NH2 MOST STABLE LEAST STABLE 3 4. consider Molecule B below, another derivative of Ndemethylglycopyrrolate. Draw the expected Fischer Projection for this derivative molecule in the box. (You may abbreviate the benzene ring as "phenyl".) N OH H3C Br OH = CH3 OH CH2 Cl H Br N Molecule B OH Cl H CH 5. CH2 NOMENCLATURE! Use the appropriate IUPAC notation to name or draw each of the organic structures below: A. trans-1,4-dibutylcyclohexane CH2CH2CH2CH3 H3CH2CH2CH2C B. 6-ethyl-2-methyl-4,4-dipropyloctane C. cis-1,2-diethylcyclopropene 4 I HO D. 1 E. 8 F m-fluoroiodobenzene trans-3-methyl-6-propyl-6-octen-2-ol 5-methyl-2-heptyne F. 6. REACTIONS! Draw the expected reactant or product for each reaction below, and write the accompanying mechanism where requested. If no reaction is expected to occur, write "NR". 5 Cl A. HCl Show mechanism: H Cl Cl OH B. H2O H2SO4 Show mechanism: H HO H OH2 excess H2 Pt C. D. Br2 CHBr3 NR; aromatic E. Br2 CHBr3 H2 Pd OH F + O2 6 OH2 7. Fill-in the following chart below with respect to the three listed drugs: Medicinal/Pharmaceutical Use? Drug Effective for the treatment of high blood pressure and congestive heart failure Active as a pain and fever reliever Used to treat morning sickness and found to be useful in the treatment of leprosy and may also be useful in the treatment of AIDS Captopril Ibuprofen Thalidomide 8. S-enantiomer Racemic Mixture R-enantiomer (as S is found to be teratogenic) Arrange the following compounds in order of expected increasing boiling point, and briefly explain your ordering: < < 9. Manufactured? (i.e., Renantiomer/Senantiomer/Racemic Mixture) < < A. List all the intermolecular forces that need to be overcome for the compound A given below to boil? H OH N O O O O N 7 . B. LDF, dipole-dipole, hydrogen bonding For each of the molecules below , circle whether you would expect it to have a higher or lower boiling point than compound A above. Briefly explain your answer. OH HO O N H NH2 HIGHER LOWER This molecule has an aromatic ring in place of cyclohexane in compound A. Aromatic ring is more stable and hence boiling point is higher. OH HO O HIGHER LOWER Two amine groups are replaced by methyl. So lower hydrogen bonding in this molecule. Hence lower boiling point. 8