Question

Section 2.9 introduced the idea of structural isomerism, with 1-propanol and 2 -propanol as examples. Determine which of these properties would distinguish these two substances: (a) boiling point; (b) combustion analysis results; (c) molecular weight; (d) density at a given temperature and pressure. You can check on the properties of these two compounds in Wolfram Alpha (http://www.wolframalpha.com/) or the CRC Handbook of Chemistry and Physics.

Short answer

The properties that can distinguish between 1-propanol and 2-propanol are boiling point and density at a given temperature and pressure. The boiling points of 1-propanol and 2-propanol are 370.8 K (97.2°C) and 355.4 K (82.4°C), respectively. The densities of 1-propanol and 2-propanol at 20°C are 0.803 g/mL and 0.785 g/mL, respectively. Combustion analysis results and molecular weight cannot be used to differentiate the two isomers as they have the same molecular formula (C3H8O) and molecular weight (60.1 g/mol).

Step-by-step solution

Structural Formulae of 1-Propanol and 2-Propanol

Firstly, we need to know the structural formulae of both isomers of propanol. The structural formula represents the arrangement of atoms in a molecule. 1-Propanol: CH3─CH2─CH2─OH 2-Propanol: CH3─CH(OH)─CH3 Now that we know the structure of both isomers, we can analyze each property to determine if it can distinguish between the two isomers.

Boiling Point

The boiling point of a substance depends on the intermolecular forces between its molecules. These forces include hydrogen bonding, dipole-dipole interactions, and van der Waals forces. For 1-propanol and 2-propanol, both exhibit hydrogen bonding due to the presence of the -OH group. However, their boiling points may differ due to the difference in molecular structure, and hence, the geometry of the hydrogen bonding. Using the given resources, we can find the boiling points: - 1-Propanol: 370.8 K (97.2°C) - 2-Propanol: 355.4 K (82.4°C) Since the boiling points are different, this property can be used to distinguish between 1-propanol and 2-propanol.

Combustion Analysis Results

Combustion analysis results give us information about the amount of carbon, hydrogen, and oxygen present in a molecule when it is combusted. Since 1-propanol and 2-propanol are structural isomers, they have the same molecular formula (C3H8O). Hence, when combusted, they would produce the same amounts of CO2 and H2O. Therefore, combustion analysis results will not distinguish between these two substances.

Molecular Weight

The molecular weight of a substance is the sum of the atomic weights of all atoms in its molecule. Since 1-propanol and 2-propanol are structural isomers, they both have the same molecular formula (C3H8O) and therefore, the same molecular weight (60.1 g/mol). Thus, molecular weight cannot be used to distinguish between the two isomers.

Density at a Given Temperature and Pressure

Density is the mass of a substance divided by its volume. Since 1-propanol and 2-propanol have different molecular structures and packing arrangements, their densities at the same temperature and pressure can be different. Using the resources provided, we can find the densities: - 1-Propanol: 0.803 g/mL at 20°C - 2-Propanol: 0.785 g/mL at 20°C Different densities can be used to distinguish between the two isomers at a given temperature and pressure. In summary, boiling point and density at a given temperature and pressure can distinguish between 1-propanol and 2-propanol, while combustion analysis results and molecular weight cannot.

Key concepts

Boiling Point

The boiling point of a compound is a key characteristic influenced by its intermolecular forces. These forces can include hydrogen bonding, dipole-dipole interactions, and van der Waals forces. Understanding these forces is crucial when comparing structural isomers like 1-propanol and 2-propanol.
Both 1-propanol and 2-propanol have the ability to form hydrogen bonds due to the presence of the hydroxyl (-OH) group. However, the difference in their molecular structures affects the strength and orientation of these hydrogen bonds, leading to a difference in their boiling points.
Here are the boiling points of these two isomers:

• 1-Propanol: 370.8 K (97.2°C)
• 2-Propanol: 355.4 K (82.4°C)

The higher boiling point of 1-propanol indicates stronger intermolecular forces compared to 2-propanol. This difference in boiling points is a useful property to distinguish between the two isomers. The arrangement of atoms and the resulting molecular geometry affect the efficiency of hydrogen bonding, making it a distinctive factor.

Density

Density is defined as the mass per unit volume and can provide insights into the molecular structure of substances. For structural isomers, like 1-propanol and 2-propanol, their packing efficiencies affect how densely the molecules can occupy a space.
When observing liquids like these isomers at the same temperature and pressure, differences in density can reveal how compactly the molecules are arranged.
The densities for these isomers at 20°C are:

• 1-Propanol: 0.803 g/mL
• 2-Propanol: 0.785 g/mL

1-propanol is slightly denser than 2-propanol. This suggests that the linear structure of 1-propanol allows for closer packing of molecules compared to the more branched structure of 2-propanol. Due to their different packing arrangements, analyzing density provides a valid method to distinguish between the two structural isomers.

Molecular Structure

Molecular structure refers to the three-dimensional arrangement of atoms within a molecule. This structure significantly impacts physical properties such as boiling points and densities, as demonstrated in structural isomers like 1-propanol and 2-propanol.
1-propanol (CH₃─CH₂─CH₂─OH) has a linear structure, while 2-propanol (CH₃─CH(OH)─CH₃) possesses a more branched configuration. This difference in connectivity affects how molecules interact with each other.

• Linear structures, like in 1-propanol, tend to have higher boiling points due to more extensive surface contact, which enhances van der Waals forces.
• Branched structures, like in 2-propanol, typically result in slightly lower boiling points due to lower surface contact.

Molecular structure helps in understanding how molecules behave both on their own and when exposed to external conditions. The specific arrangement within a molecule influences various aspects such as hydrogen bonding strength, how well molecules can fit together (density), and their overall interactions with surroundings.