Chemistry M11 Spring 2010 Examination #3 ANSWER KEY pp. 1

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1 Chemistry M11 Spring 2010 Examination #3 ASWER KEY pp. 1 or Questions 1 2, consider the hydrogenation of trans-3-methyl-2-pentene in the presence of a transition metal catalyst. 1. C Determine the major product for this reaction. A. B. C. D. E. 2. D Which of the statements below correctly describes this reaction? A. The major product involves formation of a primary alcohol. B. The major product involves formation of a secondary alcohol. C. The major product involves formation of a tertiary alcohol. D. The major product involves formation of an alkane. E. The major product involves formation of an alkyne. 3. D ow many structural isomers exist for C 6 14? A. 2 B. 3 C. 4 D. 5 E A Select the most reactive cyclic compound below: A. cyclopropane B. cyclobutane C. cyclopentane D. cyclohexane E. cyclooctane

2 Chemistry M11 Spring 2010 Examination #3 ASWER KEY pp A The structure of m-dibromobenzene is shown by which of the structures below? A. B. C. D. E. or Questions 6 10, select the properly described drug(s) from the choices below: A. Captopril B. Ibuprofen C. Thalidomide D. All of the above E. one of the above 6. B This drug is sold as a racemic mixture. 7. C While both enantiomers of this drug are active sedatives, its S-enantiomer is teratogenic. 8. A This drug is manufactured and sold as the S, S-stereoisomer. 9. B The S-enantiomer of this drug is active as a pain and fever reliever. 10. A This drug is effective in the treatment of high blood pressure and congestive heart failure.

3 Chemistry M11 Spring 2010 Examination #3 ASWER KEY pp D Which ischer projection below correctly represents the molecule shown? C 2 A. C C 2 D. C C 2 B. C E. C C 2 C 2 C C. C A Determine the compound below with the greatest expected boiling point: A. B. C. D. E.

4 Chemistry M11 Spring 2010 Examination #3 ASWER KEY pp D Select the pair of functional groups below with the most similar chemical properties: A. alkanes and carboxylic acidcs B. alkenes and aromatics C. amines and esters D. ketones and aldehydes E. alkynes and amides or Questions 14 16, select the correct IUPAC name for each of the provided organic compounds: 14. A. 6-hydroxy-6-methyl-2-heptyne B. 6-methyl-2-heptyn-6-ol C. 2-methyl-5-heptyn-2-ol D. 2-hydroxy-2-methyl-5-heptyne E. 1, 1-dimethyl-4-hexynol 15. A. cis-4-methyl-5-propyl-2-hexene B. trans-4-methyl-5-propyl-2-hexene C. 1, 3, 4-trimethylheptene D. cis-4, 5-dimethyl-2-octene E. trans-4, 5-dimethyl-2-octene 16. A. 2-bromo-3-ethylbutane B. 3-ethyl-2-bromobutane C. 3-methyl-4-bromopentane D. 4-bromo-3-methylpentane E. 2-bromo-3-methylpentane

5 Chemistry M11 Spring 2010 Examination #3 ASWER KEY pp Indicate the organic starting material (marked with a?) required for the following reaction to occur:? Cl 2 CCl 3 Cl Cl A. butane B. 1-butene C. 2-butene D. propene E. 2-methylpropene or Questions 18 19, consider the molecule shown below: C 3 Cl 3 C 2 C R S S R C 3 C Which of the following statements CRRECTLY describes the molecule? A. It possesses 1 enantiomer and 14 diastereomers. B. It possesses 1 enantiomer and 15 diastereomers. C. It possesses 2 enantiomers and 13 diastereomers. D. It possesses 2 enantiomers and 14 diastereomers. E. It possesses 1 enantiomer and 30 diastereomers. 19. ow many R-stereocenters (if any) are present in the molecule? A. 0 B. 1 C. 2 D. 3 E. 4

6 Chemistry M11 Spring 2010 Examination #3 ASWER KEY pp Select the ICRRECT statement below: A. Constitutional isomers possess the same molecular formula but different connectivity of atoms, resulting in their varied physical and chemical properties. B. Enantiomers possess the same molecular formula, same connectivity, but different spatial arrangements of atoms with a nonsuperimposable mirror image. C. Diastereomers possess the same molecular formula, same connectivity, different spatial arrangements of atoms, and are not mirror images. D. A pair of enantiomers rotates plane polarized light by equal amounts in opposite directions. E. A racemic mixture is an equimolar mixture of two enantiomers that rotates plane polarized light in both directions. ED MULTIPLE CICE 21. (49 pts. total) Consider Ciprofloxacin ydrochloride, a synthetic, sterile, multiple dose antibacterial antimicrobial for topical ophthalmic use with in vitro activity against a wide range of gram-negative and gram-positive organisms. The bactericidal action of Ciprofloxacin results from interference with the enzyme DA gyrase, which is needed for the synthesis of bacterial DA. alkyl halide ketone carboxylic acid C 2 alkene Cl 2 amine A. (4 pts.) Complete the molecular formula of this compound by filling-in the blanks below each listed atom: C Cl 2 B. (5 pts.) Identify and label IVE DIERET functional groups present in the structure above. See above; could also identify the aromatic ring as a functional group.

7 Chemistry M11 Spring 2010 Examination #3 ASWER KEY pp. 7 C 2 Cl 2 most unstable C. (2 pts.) Are there any aromatic components present in Ciprofloxacin ydrochloride? If so, circle them in the structure on the top of the page. If not, write E. See above D. (4 pts.) Is Ciprofloxacin ydrochloride expected to exhibit optical isomerism? iefly explain why or why not. This molecule does T exhibit optical isomerism as it does not possess any chiral centers. E. (4 pts.) Which component in Ciprofloxacin ydrochloride is considered the most unstable? iefly explain your choice. The cyclopropane component (labeled above) is predicted to be the most unstable due to inherent ring strain (i.e., tetrahedral carbons desire bond angles but instead exhibit 60 0 bond angles).. (8 pts. total; 4 pts. each) or each of the following molecules below, circle whether you would expect it to have a IGER or LWER boiling point than Ciprofloxacin ydrochloride (shown above). iefly explain your answer. C 2 Cl 2 would have a (CIRCLE E) higher lower boiling point than Ciprofloxacin ydrochloride. EXPLAATI: Lack of aromaticity due to the disappearance of the benzene ring will serve to decrease the overall number of dispersion forces present. C 2 Cl 2 would have a (CIRCLE E) higher lower boiling point than Ciprofloxacin ydrochloride. EXPLAATI: Increase in surface area by six-membered cyclohexane ring (contrasted with three-membered cyclopropane ring) serves to increase the overall number of dispersion forces present.

8 Chemistry M11 Spring 2010 Examination #3 ASWER KEY pp. 8 In pharmaceutical research, structural analogs of drugs are often made in order to determine if they possess similar biological properties. Below is a structural analog (or derivative) of Ciprofloxacin ydrochloride which will be used to answer the remaining parts G I: C 2 R R 2 RR' (for simplicity) G. (8 pts.) In the boxes below, draw the most stable and less stable chair conformations of the derivative molecule: RR' R 2 R R'R R R 2 Less Stable Most Stable. (6 pts.) Label AY and ALL primary, secondary, and/or tertiary amines present in the derivative molecule shown below: C 2 secondary tertiary tertiary

9 Chemistry M11 Spring 2010 Examination #3 ASWER KEY pp. 9 C 2 I. (8 pts.) inally, compare each molecule below with the derivative molecule (shown above). In the box below each structure, write identical, enantiomer, diastereomer, or none of these. note: T a carboxylic acid! C 2 2 C Enantiomer one of these C 2 2 C Diastereomer Enantiomer

10 Chemistry M11 Spring 2010 Examination #3 ASWER KEY pp (11 pts. total) REACTIS AD MECAISMS! A. (6 pts.) In the box below, write an example of a YDRATI reaction covered during this unit. Make sure to completely label your reactant(s) and product(s) along with the reagent(s) necessary to perform the conversion. Underneath the box, give the appropriate mechanism or curved arrow formalism (i.e., arrow notation) which demonstrates product(s) formation. Many possible answers here! S 4 mechanism: product B. (5 pts.) In the box below, write an example of a YDRALGEATI reaction covered during this unit. Make sure to completely label your reactant(s) and product(s) along with the reagent(s) necessary to perform the conversion. Underneath the box, give the appropriate mechanism or curved arrow formalism (i.e., arrow notation) which demonstrates product(s) formation. Many possible answers here! + I I mechanism: I - I I