3. Properties of Isomers (6 pts total) (a) (2 pts) Consider the following illustration of a protein binding pocket and two enantiomers. Assuming the most stabilizing interaction is an ionic bond between the ammonium (NH3*) and the carboxylate (CO2), circle the enantiomer that has higher affinity for (i.e., binds more strongly to) the protein? OH +H3N. hypothetical protein binding pocket = generic bulky group HO.. um HO enantiomer A enantiomer B (b) (4 pts) Compounds A and B undergo a reaction with an acid chloride to give compounds C and D as shown below. Complete the table, indicating by writing “yes” or “no” whether SiO2 chromatography and chiral chromatography can be used to separate compounds A and B, and compounds B and D. H3CO CF3 .CI OH OH CH3 CH3 base, solvent A B L CH3 C H3CO CF3 H3CO CF3 Molecules H3CO CF3 °. OH OH CH3 CH3 B H3CO CF3 ""CH3 CH3 Separable by SiO2 chromatography (yes or no) """CH3 Separable by chiral chromatography (yes or no) 2. Chirality (7.5 pts total) For each of the following molecules, assign the molecule as chiral or achiral. (a) (b) (c) (d) (e) H H3C CH3 HO H H CH3 H CI X CI CH3 H, H3C OH CH3 H3C H H H₂N CH3

5:51 Draw examples of the following: (a) A meso compound with the formula C8H18 (b) A meso compound with the formula C9H20 (c) A compound with two chirality centers, one R and the other S

5. Assign R or S configuration to each chirality center in the following molecules: CH3 CH3 Br (a) Br (b) (c) HaCH3 HaBr H OH CH3 H3C H OH H CH3 OH Which of these compounds are enantiomers, and which are diastereomers?

Identify the relationship between the following pair of structures by describing them as represting enantiomers, diastereomers, constitutional isomers or two molecules of the same compounds (a) (c) H CH3 Br. CH3 Br f-f and Filmas H H CH3 H F Oll H CHO Br X-X ²=-= -OH HO and and H Br H- F C(O)CH, H (b) CH3 (d) H- and HO CHO -H -OH C(O)CH3

Identify the relationship between the following pair of structures by describing them as represting enantiomers, diastereomers, constitutional isomers or two molecules of the same compounds (a) (c) H H₂C H F Br Oll F CH3 Br H and Br. CH3 H and Fumus (d) H H X-X=-= CH3 H CH3 (b) Br HO CHO and -OH H C(O)CH3 and HO H- CHO -H -OH C(O)CH3

(c) (i) (ii) Assign each of the following molecules as chiral or achiral. CH3 S HO OH H3C H Br H" Br CH3

5-51 Draw examples of the following: (a) A meso compound with the formula C8H18 (b) A meso compound with the formula C9H20 (c) A compound with two chirality centers, one Rand the other S

4. Answer the following question for the molecule shown: (a)How many chirality centers does it have? Identify them. (b)How many stereoisomers of are there? (c)Draw the structure of the enantiomers. (d)Draw the structure of a diastereomers. сно но

4. Assign R,S configurations to the following molecules: (a) Br (b) H (c) NH2 H3C-CO2H HOC-CO2H CH3 NCC-CH3 H. H 5. Assign R or S configuration to each chirality center in the following molecules: (a) CH3 Br H Br (b) CH3 Br (c) H CH3 Ha H3C H OH OH H OH H "CH3 CH3 Which of these compounds are enantiomers, and which are diastereomers?

2.) For the following 12 compounds, please write the number of chiral centers (0 if there are none) and label each molecule as either chiral or achiral. H3C H3C, но, H3C H3C H3C H3C H3C" H3C CH3 CHs OH он он H3C он он H3C., он H3C, H3C H3C H3C он но H3C ÓH H3C H3C H3C" но OH он CH3