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Chapter 21: Problem 115

The two isomers having the formula \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}\) boil at \(-23^{\circ} \mathrm{C}\) and \(78.5^{\circ} \mathrm{C} .\) Draw the structure of the isomer that boils at \(-23^{\circ} \mathrm{C}\) and of the isomer that boils at \(78.5^{\circ} \mathrm{C}.\)

Short Answer

Expert verified
The isomer with the boiling point of -23°C is dimethyl ether, having the structure: O || CH3 - - CH3 The isomer with the boiling point of 78.5°C is ethanol, having the structure: CH3 - CH2 - OH

Step by step solution

01

Identify possible isomers with the given formula

With the formula \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}\), we can identify the two possible isomers: ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3). The next step is to determine which isomer corresponds to each boiling point.
02

Analyze the boiling points

Generally, the greater the intermolecular forces, the higher the boiling point of the compound. Ethanol has a hydroxyl group (-OH), which can form hydrogen bonds, a stronger intermolecular force than the dipole-dipole interactions in dimethyl ether. Therefore, we can conclude that the isomer with the higher boiling point (78.5°C) should be ethanol, while the one with the lower boiling point (-23°C) should be dimethyl ether.
03

Draw the structures

We now know which isomer corresponds to each boiling point, so we can draw their structures: 1. For the isomer that boils at -23°C (dimethyl ether): O || CH3 - - CH3 2. For the isomer that boils at 78.5°C (ethanol): CH3 - CH2 - OH

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