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

Previous problemNext problem

7:05 minutes

Problem 7c

Textbook Question

Predict which member of each pair will be more acidic. Explain your answers.
c. 2-chloroethanol or 2,2-dichloroethanol

Verified step by step guidance

Identify the functional group in both compounds. Both 2-chloroethanol and 2,2-dichloroethanol contain a hydroxyl (-OH) group, making them alcohols. The acidity of alcohols is influenced by the stability of the conjugate base formed after deprotonation.

Analyze the substituents attached to the carbon chain. In 2-chloroethanol, there is one chlorine atom attached to the carbon adjacent to the hydroxyl group. In 2,2-dichloroethanol, there are two chlorine atoms attached to the same carbon adjacent to the hydroxyl group.

Consider the inductive effect of chlorine atoms. Chlorine is an electronegative atom, and its presence withdraws electron density through the sigma bond (inductive effect). This stabilizes the conjugate base (alkoxide ion) by delocalizing the negative charge.

Compare the extent of the inductive effect in both compounds. In 2,2-dichloroethanol, the presence of two chlorine atoms exerts a stronger inductive effect compared to the single chlorine atom in 2-chloroethanol. This makes the conjugate base of 2,2-dichloroethanol more stable.

Conclude that 2,2-dichloroethanol is more acidic than 2-chloroethanol because the stronger inductive effect from the two chlorine atoms leads to greater stabilization of the conjugate base, making it easier for the hydroxyl group to lose a proton.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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 structure and acidity is crucial for predicting which compound in a pair will be more acidic.

Inductive Effect

The inductive effect describes how the presence of electronegative atoms or groups can stabilize or destabilize a negative charge in a molecule. In the context of acidity, electron-withdrawing groups, such as chlorine, can increase acidity by stabilizing the conjugate base formed after deprotonation. This effect is particularly relevant when comparing compounds with different substituents.

Comparative Analysis of Substituents

When comparing the acidity of two compounds, it is essential to analyze the nature and position of substituents. In this case, 2-chloroethanol has one chlorine atom, while 2,2-dichloroethanol has two. The additional chlorine in the latter compound enhances the inductive effect, leading to greater stabilization of the conjugate base and thus increased acidity.