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Arrange the following gem-diols in the order of increasing stability in dilute aqueous acid: HO OH . CH3 НО ОН H3C лон "I CH3 НО ОН н Cl3C III HO OH Н IV

Arrange the following gem-diols in the order of increasing stability in dilute aqueous acid: HO OH . CH3 НО ОН H3C лон "I CH3 НО ОН н Cl3C III HO OH Н IV

Chemistry
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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**Arrangement of Gem-diols in Order of Increasing Stability** The task is to arrange the following gem-diols in the order of increasing stability when placed in dilute aqueous acid: 1. **Structure I:** - Configuration: A three-carbon chain with two hydroxyl (OH) groups attached to a central carbon that also bears two methyl groups (CH₃). 2. **Structure II:** - Configuration: A four-carbon chain with two hydroxyl (OH) groups attached to a central carbon that also bears two methyl (CH₃) groups, each on adjacent carbon atoms. 3. **Structure III:** - Configuration: A two-carbon chain with two hydroxyl (OH) groups and one chloroform group (Cl₃C) attached to the central carbon. 4. **Structure IV:** - Configuration: A two-carbon chain with two hydroxyl (OH) groups and one methyl group (CH₃) attached to the central carbon. **Explanation of Stability:** The stability of gem-diols in aqueous environments often depends on the electronic and steric effects of the substituents attached to the central carbon. Electron-withdrawing groups, such as the chloroform group in Structure III, tend to stabilize the gem-diol structure by making the central carbon less electron rich and thus more accommodating to the electron-donating hydroxyl groups. Comparatively, structures with more electron-donating groups (like methyl groups) may be less stable due to increased electron density at the central carbon. In summary, to determine the order of stability among these compounds, consider the nature of the substituents (electron-withdrawing vs. electron-donating) and the steric hindrance they cause.
Transcribed Image Text:**Arrangement of Gem-diols in Order of Increasing Stability** The task is to arrange the following gem-diols in the order of increasing stability when placed in dilute aqueous acid: 1. **Structure I:** - Configuration: A three-carbon chain with two hydroxyl (OH) groups attached to a central carbon that also bears two methyl groups (CH₃). 2. **Structure II:** - Configuration: A four-carbon chain with two hydroxyl (OH) groups attached to a central carbon that also bears two methyl (CH₃) groups, each on adjacent carbon atoms. 3. **Structure III:** - Configuration: A two-carbon chain with two hydroxyl (OH) groups and one chloroform group (Cl₃C) attached to the central carbon. 4. **Structure IV:** - Configuration: A two-carbon chain with two hydroxyl (OH) groups and one methyl group (CH₃) attached to the central carbon. **Explanation of Stability:** The stability of gem-diols in aqueous environments often depends on the electronic and steric effects of the substituents attached to the central carbon. Electron-withdrawing groups, such as the chloroform group in Structure III, tend to stabilize the gem-diol structure by making the central carbon less electron rich and thus more accommodating to the electron-donating hydroxyl groups. Comparatively, structures with more electron-donating groups (like methyl groups) may be less stable due to increased electron density at the central carbon. In summary, to determine the order of stability among these compounds, consider the nature of the substituents (electron-withdrawing vs. electron-donating) and the steric hindrance they cause.
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