Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Which salts are formed in this acid base reaction(select all that apply
Transcribed Image Text:The image shows a chemical reaction involving stereoisomers and a nucleophilic substitution. On the left, there are two stereoisomers of 2-hydroxybutanoic acid (lactic acid) depicted. The upper molecule has an (R) configuration, and the lower one has an (S) configuration.
The reaction involves these stereoisomers with an amine, specifically isopropylamine. The arrow indicates the chemical reaction proceeds from left to right.
On the right, there are four boxed scenarios labeled A, B, C, and D, showing potential products:
- **A**: The lactic acid with (R) configuration reacts to form an amide where the hydroxyl group is replaced by a deprotonated amide group, maintaining the original stereochemistry. The isopropylamine part is shown below, indicating a separate ionic interaction with the carboxylate.
- **B**: Similar to A but with an inversion of configuration at the hydroxyl carbon, leading to the (S) configuration amide. The carboxylate ion is coordinated with the isopropylammonium ion.
- **C**: The lactic acid with (S) configuration reacts to form an amide with retention of configuration at the chiral center, with the isopropylamine forming an ionic pair shown adjacent to the amide.
- **D**: Shows an inversion to the (R) configuration at the center where substitution occurs, with a similar ionic interaction as in the above cases.
These scenarios illustrate how stereochemical configurations can influence the outcome of nucleophilic substitution reactions, particularly regarding retention or inversion of configuration at the stereocenter.
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