Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Nomenclature

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Nomenclature

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6:05 minutes

Problem 7d

Textbook Question

Predict which member of each pair will be more acidic. Explain your answers.
d. 2,2-dichloropropan-1-ol or 2,2-difluoropropan-1-ol

Verified step by step guidance

Step 1: Recall the concept of acidity in organic compounds. Acidity is influenced by the stability of the conjugate base formed after the compound donates a proton (H⁺). The more stable the conjugate base, the more acidic the compound.

Step 2: Analyze the structures of the two compounds. Both compounds are alcohols (propan-1-ol derivatives) with halogen substituents at the 2,2-position. The halogens (chlorine and fluorine) are electronegative and can stabilize the conjugate base through inductive effects.

Step 3: Compare the electronegativity of chlorine and fluorine. Fluorine is more electronegative than chlorine, meaning it exerts a stronger inductive effect. This stronger inductive effect stabilizes the conjugate base of 2,2-difluoropropan-1-ol more effectively than the conjugate base of 2,2-dichloropropan-1-ol.

Step 4: Consider the impact of the inductive effect on acidity. The stronger inductive effect of fluorine in 2,2-difluoropropan-1-ol increases the acidity of the compound compared to 2,2-dichloropropan-1-ol.

Step 5: Conclude that 2,2-difluoropropan-1-ol is more acidic than 2,2-dichloropropan-1-ol due to the greater electronegativity of fluorine, which stabilizes the conjugate base more effectively through a stronger inductive effect.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acidity and pKa

Acidity in organic chemistry refers to the tendency of a compound to donate a proton (H+). The strength of an acid is often measured by its pKa value; lower pKa values indicate stronger acids. Understanding the relationship between molecular structure and acidity is crucial for predicting which compound will be more acidic in a given comparison.

Inductive Effect

The inductive effect describes how the presence of electronegative atoms or groups in a molecule can influence the acidity of a nearby acidic proton. Electronegative atoms, such as chlorine and fluorine, can stabilize the negative charge on the conjugate base formed after deprotonation, thereby increasing acidity. The strength of this effect varies with the electronegativity and distance of the substituents from the acidic site.

Comparative Analysis of Substituents

When comparing the acidity of two compounds, it is essential to analyze the substituents attached to the carbon bearing the hydroxyl group. In this case, 2,2-dichloropropan-1-ol and 2,2-difluoropropan-1-ol have different halogen substituents, which will affect their acidity. The more electronegative fluorine is expected to exert a stronger inductive effect than chlorine, leading to a greater stabilization of the conjugate base and thus a higher acidity for the difluorinated compound.