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Arrange the following compounds in order of increasing acidity (from least acidic to most acidic): OH IV

Arrange the following compounds in order of increasing acidity (from least acidic to most acidic): OH 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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### Arranging Organic Compounds by Acid Strength #### Objective: Arrange the following compounds in order of increasing acidity (from least acidic to most acidic). #### Compounds and Structures: 1. **Compound I**: - Structure: Acetone (a simple ketone with the structure CH3-CO-CH3) - Image representation: A carbonyl group (C=O) with two methyl groups attached. 2. **Compound II**: - Structure: Benzene (C6H6) - Image representation: A hexagonal ring with alternate double bonds (aromatic ring). 3. **Compound III**: - Structure: Diacetyl (a diketone with the structure CH3-CO-CO-CH3) - Image representation: Two carbonyl groups (C=O) bonded to the same carbon chain. 4. **Compound IV**: - Structure: Cyclohexanol (a cycloalcohol with the structure C6H11OH) - Image representation: A hexagonal ring with a hydroxyl group (-OH) attached. ### Explanation of Increasing Acidity: In organic chemistry, acidity depends on several factors, including the stability of the conjugate base, the inductive effect, and the resonance effect. 1. **Compound II - Benzene**: Benzene is neutral and does not have any acidic protons. 2. **Compound IV - Cyclohexanol**: The alcohol group can donate a proton, but due to the induction and lack of resonance stabilization, it's less acidic. 3. **Compound I - Acetone**: The alpha-hydrogen atoms (adjacent to the carbonyl group) are more acidic due to the electron-withdrawing effect of the carbonyl group. 4. **Compound III - Diacetyl**: Diacetyl has two carbonyl groups, which significantly enhance the acidity of the alpha-hydrogens compared to a single carbonyl group. ### Ordered List of Compounds by Increasing Acidity: 1. Compound II – Benzene 2. Compound IV – Cyclohexanol 3. Compound I – Acetone 4. Compound III – Diacetyl Understanding the acidity of different compounds is crucial for predicting their reactivity and behavior in various chemical reactions.
Transcribed Image Text:### Arranging Organic Compounds by Acid Strength #### Objective: Arrange the following compounds in order of increasing acidity (from least acidic to most acidic). #### Compounds and Structures: 1. **Compound I**: - Structure: Acetone (a simple ketone with the structure CH3-CO-CH3) - Image representation: A carbonyl group (C=O) with two methyl groups attached. 2. **Compound II**: - Structure: Benzene (C6H6) - Image representation: A hexagonal ring with alternate double bonds (aromatic ring). 3. **Compound III**: - Structure: Diacetyl (a diketone with the structure CH3-CO-CO-CH3) - Image representation: Two carbonyl groups (C=O) bonded to the same carbon chain. 4. **Compound IV**: - Structure: Cyclohexanol (a cycloalcohol with the structure C6H11OH) - Image representation: A hexagonal ring with a hydroxyl group (-OH) attached. ### Explanation of Increasing Acidity: In organic chemistry, acidity depends on several factors, including the stability of the conjugate base, the inductive effect, and the resonance effect. 1. **Compound II - Benzene**: Benzene is neutral and does not have any acidic protons. 2. **Compound IV - Cyclohexanol**: The alcohol group can donate a proton, but due to the induction and lack of resonance stabilization, it's less acidic. 3. **Compound I - Acetone**: The alpha-hydrogen atoms (adjacent to the carbonyl group) are more acidic due to the electron-withdrawing effect of the carbonyl group. 4. **Compound III - Diacetyl**: Diacetyl has two carbonyl groups, which significantly enhance the acidity of the alpha-hydrogens compared to a single carbonyl group. ### Ordered List of Compounds by Increasing Acidity: 1. Compound II – Benzene 2. Compound IV – Cyclohexanol 3. Compound I – Acetone 4. Compound III – Diacetyl Understanding the acidity of different compounds is crucial for predicting their reactivity and behavior in various chemical reactions.
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