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Q1.25(vi):
Amongst the following compounds, identify which are insoluble, partially soluble and highly soluble in water? (vi) pentanol.

Solution :

Step 1: Chemical Structure and Composition

Pentanol ($C_5H_{11}OH$) is a straight-chain primary alcohol consisting of a hydrophobic alkyl chain (pentyl group, $C_5H_{11}-$) and a hydrophilic hydroxyl group ($-OH$). [Per the concept of molecular polarity and the principle of 'like dissolves like'].

Step 2: Thermodynamic Analysis of Solubility

The solubility of alcohols in water is governed by two competing factors:

  • Hydrophilic interaction: The $-OH$ group can form hydrogen bonds with water molecules, promoting solubility.
  • Hydrophobic effect: The $C_5$ alkyl chain is non-polar and disrupts the hydrogen-bonded network of water without offering favorable dispersion forces strong enough to compensate for the entropy loss.

Step 3: Evaluating the Hydrophobic-Hydrophilic Ratio

As the carbon chain length increases in a homologous series of alcohols, the hydrophobic character dominates. Methanol ($C_1$), ethanol ($C_2$), and propanol ($C_3$) are completely miscible. However, as we progress to butanol ($C_4$) and pentanol ($C_5$), the increasing non-polar nature significantly restricts solubility.

Alcohol Solubility Trend
Methanol to Propanol Highly Soluble (Miscible)
Butanol Partially Soluble
Pentanol Partially Soluble (Low Solubility)

Step 4: Molecular Visualization of Interaction

Hydrophobic Chain (C5H11) OH (Polar) H2O Molecules

Step 5: Conclusion on Solubility Classification

Pentanol possesses a sufficient alkyl chain length to render the hydrocarbon part significantly hydrophobic. While the hydroxyl group allows for some hydrogen bonding, it is insufficient to pull the five-carbon chain into the aqueous phase entirely. Therefore, pentanol exhibits limited solubility in water.

Final Solution: Pentanol is partially soluble in water.


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