Arrange in order of increasing boiling points....butane,butanoic acid, and methyl propane

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Organic Chemistry trend question: branching of hydrocarbons increase boiling point. Hydrogen bonding also increases boiling point, more so than branching.

Butanoic acid is able to form H-bonds with itself. Methyl propane is branched.

Butanoic acid > Methyl propane >Butane

To determine the order of increasing boiling points for the given compounds (butane, butanoic acid, and methyl propane), we need to consider their molecular structures and intermolecular forces.

1. Butane (C4H10): Butane is an alkane with a straight carbon chain consisting of four carbon atoms. It exhibits London dispersion forces as the only intermolecular force due to its nonpolar nature. The boiling point depends on the strength of these intermolecular forces.

2. Methyl propane (C4H10): Methyl propane, also known as 2-methylpropane or isobutane, has a branched structure. It also exhibits London dispersion forces, similar to butane, but the branching of the molecule affects the arrangement of molecules, resulting in weaker intermolecular forces.

3. Butanoic Acid (C4H8O2): Butanoic acid consists of a straight carbon chain (butyl) with a carboxylic acid group (-COOH) attached at the end. The presence of the carboxylic acid group introduces additional intermolecular forces, such as hydrogen bonding. Hydrogen bonding is stronger than London dispersion forces, leading to higher boiling points compared to the other two compounds.

Considering the information above, we can arrange the compounds in order of increasing boiling points as follows:

Methyl propane < Butane < Butanoic acid