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7.4: Physical Properties of Alcohols

  • Page ID
    60609
    • Anonymous
    • LibreTexts

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     Learning Objectives
    • Explain why the boiling points of alcohols are higher than those of ethers and alkanes of similar molar masses.
    • Explain why alcohols and ethers of four or fewer carbon atoms are soluble in water while comparable alkanes are not soluble.

    Alcohols can be considered derivatives of water (H2O; also written as HOH).

    Like the H–O–H bond in water, the R–O–H bond is bent, and alcohol molecules are polar. This relationship is particularly apparent in small molecules and reflected in the physical and chemical properties of alcohols with low molar mass. Replacing a hydrogen atom from an alkane with an OH group allows the molecules to associate through hydrogen bonding (Figure \(\PageIndex{1}\)).

     Figure \(\PageIndex{1}\): Intermolecular Hydrogen Bonding in Methanol. The OH groups of alcohol molecules make hydrogen bonding possible.

    Recall that physical properties are determined to a large extent by the type of intermolecular forces. Table \(\PageIndex{1}\) lists the molar masses and the boiling points of some common compounds. The table shows that substances with similar molar masses can have quite different boiling points.

    Table \(\PageIndex{1}\): Comparison of Boiling Points and Molar Masses
    Formula Name Molar Mass Boiling Point (°C)
    CH4 methane 16 –164
    HOH water 18 100
    C2H6 ethane 30 –89
    CH3OH methanol 32 65
    C3H8 propane 44 –42
    CH3CH2OH ethanol 46 78
    C4H10 butane 58 –1
    CH3CH2CH2OH 1-propanol 60 97

    Alkanes are nonpolar and are thus associated only through relatively weak dispersion forces. Alkanes with one to four carbon atoms are gases at room temperature. In contrast, even methanol (with one carbon atom) is a liquid at room temperature. Hydrogen bonding greatly increases the boiling points of alcohols compared to hydrocarbons of comparable molar mass. The boiling point is a rough measure of the amount of energy necessary to separate a liquid molecule from its nearest neighbors. If the molecules interact through hydrogen bonding, a relatively large quantity of energy must be supplied to break those intermolecular attractions. Only then can the molecule escape from the liquid into the gaseous state.

    Alcohols can also engage in hydrogen bonding with water molecules (Figure \(\PageIndex{2}\)). Thus, whereas the hydrocarbons are insoluble in water, alcohols with one to three carbon atoms are completely soluble. As the length of the chain increases, however, the solubility of alcohols in water decreases; the molecules become more like hydrocarbons and less like water. The alcohol 1-decanol (CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2OH) is essentially insoluble in water. We frequently find that the borderline of solubility in a family of organic compounds occurs at four or five carbon atoms.

     Figure \(\PageIndex{2}\): Hydrogen Bonding between Methanol Molecules and Water Molecules. Hydrogen bonding between the OH of methanol and water molecules accounts for the solubility of methanol in water.

    Summary

    Alcohols have higher boiling points than do ethers and alkanes of similar molar masses because the OH group allows alcohol molecules to engage in hydrogen bonding. Alcohols of four or fewer carbon atoms are soluble in water because the alcohol molecules engage in hydrogen bonding with water molecules; comparable alkane molecules cannot engage in hydrogen bonding.


    This page titled 7.4: Physical Properties of Alcohols is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by Anonymous.