Without looking them up, rank the following compounds in decreasing order of acidity. These examples represent large classes of compounds that differ widely in acidity. water, ethanol, 2-chloroethanol, tert-butyl alcohol, ammonia, sulfuric acid, hexane, hex-1-yne, acetic acid
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Identify the functional groups present in each compound: water (H₂O), ethanol (CH₃CH₂OH), 2-chloroethanol (ClCH₂CH₂OH), tert-butyl alcohol ((CH₃)₃COH), ammonia (NH₃), sulfuric acid (H₂SO₄), hexane (C₆H₁₄), hex-1-yne (CH≡CCH₂CH₂CH₂CH₃), and acetic acid (CH₃COOH). Functional groups play a key role in determining acidity.
Recall the general trend of acidity: Strong acids (e.g., sulfuric acid) > carboxylic acids (e.g., acetic acid) > alcohols (e.g., ethanol, 2-chloroethanol, tert-butyl alcohol) > water > alkynes (e.g., hex-1-yne) > amines (e.g., ammonia) > alkanes (e.g., hexane). This trend is based on the stability of the conjugate base formed after deprotonation.
Consider the effect of electronegativity and resonance stabilization on acidity: Electronegative atoms (e.g., chlorine in 2-chloroethanol) and resonance stabilization (e.g., in acetic acid) increase acidity. For example, the chlorine atom in 2-chloroethanol withdraws electron density, stabilizing the conjugate base and increasing acidity compared to ethanol.
Analyze steric effects: Bulky groups, such as the tert-butyl group in tert-butyl alcohol, hinder solvation of the conjugate base, making the compound less acidic compared to smaller alcohols like ethanol.
Rank the compounds in decreasing order of acidity based on the above considerations: sulfuric acid > acetic acid > 2-chloroethanol > ethanol > water > tert-butyl alcohol > hex-1-yne > ammonia > hexane. This ranking reflects the increasing stability of the conjugate base and the factors influencing acidity.
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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 refers to the ability of a compound to donate a proton (H+) in a chemical reaction. The strength of an acid is often measured by its pKa value, where lower pKa values indicate stronger acids. Understanding the pKa helps in ranking compounds based on their acidity, as it provides a quantitative measure of how readily a compound can release a proton.
Different functional groups in organic compounds significantly affect their acidity. For instance, carboxylic acids (like acetic acid) are generally more acidic than alcohols due to the resonance stabilization of their conjugate bases. Halogen substituents, such as in 2-chloroethanol, can also enhance acidity through inductive effects, making the compound more likely to donate a proton.
Certain common compounds have well-established acidity rankings. For example, strong acids like sulfuric acid are much more acidic than alcohols or amines. Water is more acidic than alcohols, while hydrocarbons like hexane are considered neutral. Familiarity with these comparative acidities is essential for accurately ranking the given compounds.