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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: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter12: Chirality
Section: Chapter Questions
Problem 19E
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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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