Learning Objectives

explain why the boiling clues of alcohols are higher than those that ethers and also alkanes of similar molar masses. Define why alcohols and ethers of four or fewer carbon atoms are soluble in water while comparable alkanes are not soluble.

Like the H–O–H shortcut in water, the R–O–H shortcut is bent, and alcohol molecules are polar. This partnership is an especially apparent in little molecules and reflected in the physical and also chemical properties of alcohols through low molar mass.

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Replacing a hydrogen atom indigenous an alkane through an five group permits the molecule to associate v hydrogen bonding (Figure 14.2 "Intermolecular Hydrogen Bonding in Methanol"). Recall from chapter 8 "Solids, Liquids, and Gases" the physical properties are figured out to a large extent by the type of intermolecular forces. Table 14.3 "Comparison of cook Points and also Molar Masses" perform the molar masses and the boiling points of some common compounds. The table mirrors that building materials with comparable molar masses have the right to have quite various boiling points. Alkanes space nonpolar and also are thus linked only through reasonably weak dispersion forces. Alkanes v one to four carbon atoms space 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 contrasted to hydrocarbons of comparable molar mass. The boiling allude is a turbulent measure that the quantity of energy necessary to different a fluid molecule from its nearest neighbors. If the molecules communicate through hydrogen bonding, a relatively big quantity of energy must be gave to break those intermolecular attractions. Only then can the molecule escape native the liquid right into the gas state.

Figure 14.2 Intermolecular Hydrogen Bonding in Methanol


The OH groups of alcohol molecules do hydrogen bonding possible.

Table 14.3 compare of cook Points and Molar Masses

Formula name Molar massive Boiling suggest (°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

Alcohols can additionally engage in hydrogen bonding through water molecule (Figure 14.3 "Hydrogen Bonding in between Methanol Molecules and also Water Molecules"). Thus, vice versa, the hydrocarbons room insoluble in water, alcohols v one to three carbon atoms are totally 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 basically insoluble in water. We generally find that the borderline that solubility in a family members of organic compounds occurs at 4 or 5 carbon atoms.

Figure 14.3 Hydrogen Bonding between Methanol Molecules and Water Molecules


Hydrogen bonding between the oh of methanol and water molecule accounts for the solubility that methanol in water.

Ethanol has actually an five group and only 2 carbon atoms; 1-hexanol has actually one OH group for 6 carbon atoms and also is thus much more like a (nonpolar) hydrocarbon 보다 ethanol is.

Key Takeaways

Alcohols have higher boiling point out than perform ethers and also alkanes of comparable molar masses due to the fact that the five group allows alcohol molecule to interact in hydrogen bonding. Alcohols of four or under carbon atoms room soluble in water since the alcohol molecules communicate in hydrogen bonding with water molecules; equivalent alkane molecules cannot interact in hydrogen bonding.


Answer the following exercises without consulting tables in the text.

Arrange these alcohols in bespeak of raising boiling point: ethanol, methanol, and 1-propanol.

Which has the greater boiling point—butane or 1-propanol?

Arrange these alcohols in order of raising solubility in water: 1-butanol, methanol, and also 1-octanol.

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Arrange this compounds in stimulate of raising solubility in water: 1-butanol, ethanol, and pentane.