Rank the following compounds in order of their solubility in water. (most soluble = 1 -- least soluble = 4)--Note that for the same solubility rank the same (a tie).

(CH3)2CHOH
HOCH2CH(OH)CH2OH
CH3CH2OH
(CH3)3COH

I believe the answer(s) are as followed:

HOCH2CH(OH)CH2OH =>1
CH3CH2OH=>2
(CH3)2CHOH =>3
(CH3)3COH=>4

hmmm for some reason this did not work... How did you go about solving this problem? Could any of them be a tie?

Number 1 is the most polar, like dissolves like; the OH groups are very polar. Number 4 is the least polar. C-H bonds are nonpolar bonds and this compound has the most CH bonds. If the choices that I gave you didn't work, maybe 2 and 3 are the same.

You may want to check out 1 and 2. Both are miscible with H2O which means soluble in all proportions. I would call these a tie.

maybe my homework set online is messed up because it is not taking either of these answers :( sorry. But thank you both for your help!

To rank the compounds in order of their solubility in water, we need to consider the different factors that influence solubility. These factors include polarity, hydrogen bonding, and molecular weight.

Firstly, let's look at the molecular structures of the compounds:

(CH3)2CHOH - This is isopropyl alcohol, which has a molecular structure of CH3-CH(OH)-CH3.
HOCH2CH(OH)CH2OH - This is ethylene glycol or "glycol," which has a molecular structure of HO-CH2-CH(OH)-CH2-OH.
CH3CH2OH - This is ethanol or "ethyl alcohol," which has a molecular structure of CH3-CH2-OH.
(CH3)3COH - This is tert-butyl alcohol, which has a molecular structure of (CH3)3C-OH.

Now, let's examine the factors affecting solubility:

1. Polarity: Compounds with polar functional groups are generally more soluble in water. Polar groups in the compounds include the hydroxyl (-OH) group.

2. Hydrogen bonding: Compounds that can form hydrogen bonds with water molecules tend to be highly soluble. Hydrogen bonding occurs when a hydrogen atom is bonded to a highly electronegative atom (e.g., oxygen, nitrogen, or fluorine) and interacts with another electronegative atom.

3. Molecular weight: Smaller molecules typically have higher solubility compared to larger molecules.

Based on these factors, we can rank the compounds in order of their solubility in water:

1. HOCH2CH(OH)CH2OH (ethylene glycol) - This compound has two hydroxyl groups that can form hydrogen bonds with water molecules, making it highly soluble in water.

2. CH3CH2OH (ethanol) - Ethanol contains one hydroxyl group, making it polar and capable of hydrogen bonding with water. It has lower solubility compared to ethylene glycol due to the absence of an additional hydroxyl group.

3. (CH3)2CHOH (isopropyl alcohol) - Isopropyl alcohol has only one hydroxyl group but is still polar and can form some hydrogen bonds with water. It is less soluble than ethanol due to its larger molecular size.

4. (CH3)3COH (tert-butyl alcohol) - Tert-butyl alcohol has a nonpolar tert-butyl group and only one hydroxyl group. It is relatively nonpolar and does not form strong hydrogen bonds with water, resulting in lower solubility compared to the other compounds.

So, the ranking of the compounds in order of their solubility in water, from most soluble to least soluble, would be:

1. HOCH2CH(OH)CH2OH
2. CH3CH2OH
3. (CH3)2CHOH
4. (CH3)3COH