Final answer:
The compounds are ranked in decreasing order of acidity as: sulfuric acid, acetic acid, 2-chloroethanol, hex-1-yne, water, tert-butyl alcohol, ethanol, ammonia, and hexane, based on factors like electronegativity, inductive effects, and molecular structure.
Step-by-step explanation:
To rank the listed compounds in decreasing order of acidity, one must consider several factors influencing their acid strength. These factors include the electronegativity of atoms involved, inductive effects, bonding, and molecular stability after deprotonation.
- Sulfuric acid - A strong acid with high electronegativity and resonance stabilization.
- Acetic acid - A carboxylic acid whose acidity is increased by the electron-withdrawing effect of the carbonyl group.
- 2-chloroethanol - The chlorine atom has a significant inductive effect, increasing acidity relative to alcohols without halogens.
- Hex-1-yne - Acidity is increased due to the s-character of the sp-hybridized carbon atom bonding to the acidic hydrogen.
- Water - Less acidic than the above compounds but more acidic than alcohols due to higher electronegativity of oxygen.
- Tert-butyl alcohol - The steric hindrance of the bulky tert-butyl group decreases acidity compared to other alcohols.
- Ethanol - A typical primary alcohol with lower acidity than water.
- Ammonia - A weak base and a very weak acid because it tends to accept protons rather than donate.
- Hexane - Almost non-acidic, being a hydrocarbon with no significant acidity.
Therefore, the decreasing order of acidity is sulfuric acid > acetic acid > 2-chloroethanol > hex-1-yne > water > tert-butyl alcohol > ethanol > ammonia > hexane.