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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

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

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 55AP: Draw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?
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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)
Transcribed Image Text: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
Transcribed Image Text: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
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