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- 8. Two structures of Lipitor (a drug used to lower cholesterol) are shown below. (a) Determine the absolute configuration of each indicated stereocenter. Fill in the correct circle. (b) Determine if the two structures are the same compound or stereoisomers. Fill in the correct circle. (a) НО. Carbon a HO O OH Carbon a: OR OS Carbon b H N Carbon b: R OS of H Carbon c: OR OS OH OH Carbon c F Carbon d: R OS OH Carbon d (b) The two structures are: O the same compound O stereoisomers(A)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group? (b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.For the following molecules, draw all possible stereoisomers using line-angle formulas with wedge/dash notation. Label the stereocenters as R or S. Indicate which ones are enantiomers and which ones are diastereomers. (Remember: there are 2 stereoisomers possible for a molecule with n chiral centers) (A) (B) (C) (1 chiral center) Br OH (2 chiral centers) CI OH CH3 (3 chiral centers)
- 13. Classify the pairs of molecules as not the same molecule, structural isomers, diastereomers. enantiomers or identical. Circle any molecules that are not achiral. (a) (b) (c) F X Br. H H HY CI "Br Br H H CI H3C Br H Br I I Br CI H Br CH H H CH3 BrOne of the isomers of 1,2,3,4,5,6-hexahydroxycyclohexane, called myo-Inositol, acts as a growth factor in both animals and microorganisms. Draw the most stable chair conformation of myo-Inositol (Note: account the wedge and dash projection). Draw the most stable cis-trans stereoisomer of myo-Inositol. OH HO ОН HO "OH ОНQ2 Give the stereochemical relationships between each pair of structures. Examples are same compound, structural isomers, enantiomers, diastereomers. CH,OH CH,OH (c) ÇH, ÇH, (a) CH, CH, (b) Но HO H H OH HO-H HO H H- ОН НО H OH H- H- HO- H OH HO H H OH CH, CH, CH, CH, CH, CH, onared
- 2. Identify the type of stereoisomerism in each of the following molecules and draw the stereoisomer pair. (a) CH;CH=CHCOH (b) CgH;CH2CH(NH2)CH32 Draw all stereoisomers for the following molecules; indicate the stereochemica interrelationships (enantiomer, diastereomer, or meso) for all its possible pairs. 4) H;C CH3 Но CH3 OH CI CI Но OHPGF 2a is a prostaglandin, a group of compounds that are responsible for inflammation (Section 19.6). (a) How many tetrahedral stereogenic centers does PGF 2a contain? (b) How many double bonds can exist as cis and trans isomers? (c) Considering both double bonds and tetrahedral stereogenic centers, what is the maximum number of stereoisomers that can exist for PGF20? OH HO -CH₂CH=CH(CH₂)3COOH CH=CHCH(OH)(CH₂)4CH3 PGF₂α
- Q2 Give the stereochemical relationships between each pair of structures. Examples are same compound, structural isomers, enantiomers, diastereomers. (a) CH, CH, CHOH CHOH CH, CH, H OH HO-H H OH HO H H--CH HO- HO H H- OH HO- OH HO H H-OH CH, CH, CH, CH, CH, CH,(b) For each of the following pairs of structural formulas, indicate whether the two represent identical molecular species, constitutional isomers, enantiomers, or diastereomers. HOW HO HOlim Br Br H Br CH3 H Cl- H Br H. Cl CH3 CI H Cl H, H Cl OH Br Br1) Mark the chiral centers in the following molecules, if any, with an asterisk (*). (b) (a) НО НО НО ОН 0 OH (c) (d) *H3N-H HOT -С-0 HC-CH3 CH3 ОН
