Arrange the following compounds in order of decreasing solubility in water

1. Arrange the following compounds in order of decreasing solubility in water. Explain the basis for your decisions.
   CH₂CH₂CH₂-OH CH CH CH.CH, CH,CH-O-CH,
2. Arrange the compounds in Exercise 13.48 in order of decreasing boiling point. Explain your answer.

The Correct Answer and Explanation is :

Let’s break this down into two parts, starting with the solubility of the compounds in water:

Part 1: Order of Decreasing Solubility in Water

The compounds listed are:

1. CH₂CH₂CH₂-OH (1-propanol)
2. CH CH CH.CH (butene)
3. CH,CH-O-CH₂ (ethoxyethane)

Factors Affecting Solubility in Water:

• Hydrogen Bonding: Compounds capable of hydrogen bonding with water molecules tend to have higher solubility.
• Polarity: Polar compounds are generally more soluble in water.
• Size of the molecule: Smaller molecules are generally more soluble due to better interaction with water molecules.

Let’s evaluate the solubility for each:

1. CH₂CH₂CH₂-OH (1-propanol): This is an alcohol with an –OH group. The hydroxyl group can form hydrogen bonds with water, making it highly soluble.
2. CH,CH-O-CH₂ (ethoxyethane): This is an ether with an oxygen atom, but the oxygen is less likely to form hydrogen bonds as strongly as the –OH group in alcohols. Therefore, this compound has moderate solubility in water.
3. CH CH CH.CH (butene): This is an alkene, which is non-polar and cannot form hydrogen bonds with water. Therefore, its solubility is very low.

Order of Decreasing Solubility:
1-propanol > ethoxyethane > butene

Part 2: Order of Decreasing Boiling Point

The boiling point is influenced by factors such as molecular weight, intermolecular forces (hydrogen bonding, van der Waals forces), and molecular polarity.

• 1-propanol: Has hydrogen bonding due to the –OH group, resulting in a relatively high boiling point.
• Ethoxyethane: An ether, which has weaker intermolecular forces (mainly van der Waals), leading to a lower boiling point than alcohols.
• Butene: An alkene, with only van der Waals forces present. This results in a relatively low boiling point compared to alcohols and ethers.

Order of Decreasing Boiling Point:
1-propanol > ethoxyethane > butene

Let me create a visual representation of this.

Here is the diagram illustrating the order of solubility and boiling points for the compounds:

• The first section shows the solubility of each compound in water, with 1-propanol being the most soluble, followed by ethoxyethane, and butene the least soluble.
• The second section illustrates the boiling points, with 1-propanol having the highest boiling point, followed by ethoxyethane, and butene with the lowest boiling point.

Let me know if you need further clarification!