/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Problem 27 Which molecule would you expect ... [FREE SOLUTION] | 91Ó°ÊÓ

91Ó°ÊÓ

Which molecule would you expect to be more soluble in water, CH3CH2CH2CH2OH or HOCH2CH2CH2OH?

Short Answer

Expert verified
HOCH2CH2CH2OH is expected to be more soluble in water because it has two hydroxyl groups, allowing for more hydrogen bonding with water.

Step by step solution

01

- Identify Functional Groups

Start by examining the functional groups present in the two molecules given. The first molecule, CH3CH2CH2CH2OH, contains an alcohol group at the end of a 4-carbon chain. The second molecule, HOCH2CH2CH2OH, also contains an alcohol group, but it is at the end of a 3-carbon chain and has an additional alcohol group at the beginning.
02

- Assess Hydrophilicity of Functional Groups

The alcohol groups (-OH) present in both molecules can form hydrogen bonds with water, which makes molecules containing these groups more soluble in water. More hydroxyl groups generally means higher solubility in water.
03

- Compare the Solubility

Since HOCH2CH2CH2OH has two hydroxyl groups whereas CH3CH2CH2CH2OH has only one, the former is expected to form more hydrogen bonds with water, enhancing its solubility.
04

- Determine the More Soluble Molecule

Because HOCH2CH2CH2OH can potentially form more hydrogen bonds with water due to having more hydroxyl groups, it is expected to be more water-soluble than CH3CH2CH2CH2OH.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91Ó°ÊÓ!

Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Functional Groups in Chemistry
Functional groups are specific groups of atoms within molecules that determine the characteristics and chemical reactivity of those molecules. Understanding these groups is crucial for predicting how a molecule will interact with other substances, such as water.

Alcohols, for example, contain one or more hydroxyl (-OH) groups, which are known for their ability to engage in hydrogen bonding. Other common functional groups include carboxylic acids, aldehydes, ketones, and amines, each imparting different properties to the molecules they inhabit. The presence and number of functional groups, particularly those that can hydrogen bond, play a significant role in a molecule's solubility in water.
Hydrophilicity and Solubility
Hydrophilicity refers to the affinity of a molecule to interact with water. Molecules that are hydrophilic are typically polar, containing regions of positive and negative charge, allowing them to dissolve in water, which is a polar solvent. This polarity means that hydrophilic molecules can form electrostatic interactions with water molecules.

Solubility, in this context, is the ability of a substance to dissolve in water. The more hydrophilic a substance, the higher its solubility in water tends to be. Functional groups that contribute to hydrophilicity and, consequently, to solubility include hydroxyl groups, amino groups, and carboxyl groups, among others.
Hydrogen Bonding
Hydrogen bonding is one of the strongest types of noncovalent interactions and significantly affects the solubility of molecules in water. These bonds occur when a hydrogen atom, covalently bonded to a highly electronegative atom like oxygen or nitrogen, is attracted to a lone pair of electrons on another electronegative atom.

In the case of water solubility, molecules with functional groups capable of hydrogen bonding can form these interactions with water molecules, facilitating their dissolution. The extent of hydrogen bonding correlates with the number of opportunities a molecule has to engage with water, which is a determinant of its solubility.
Alcohol Solubility in Water
Alcohols are organic compounds characterized by the presence of one or more hydroxyl (-OH) groups. The solubility of alcohols in water is directly related to the presence and quantity of these hydroxyl groups. Since these groups can form hydrogen bonds with water molecules, an alcohol's solubility increases with the number of hydroxyl groups present.

However, the solubility also depends on the hydrocarbon chain length attached to the hydroxyl group. Shorter chains are more soluble because they are less hydrophobic, or water-fearing, than longer chains, which tend to resist dissolution in water. Therefore, an alcohol with more hydroxyl groups and a shorter hydrocarbon chain is generally more soluble than one with fewer hydroxyl groups or a longer hydrocarbon chain.

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

What is the effect of a nonvolatile solute on the vapor pressure of a liquid? Why is the vapor pressure of a solution different from the vapor pressure of the pure liquid solvent?

A solution of methanol and water has a mole fraction of water of 0.312 and a total vapor pressure of 211 torr at 39.9 C. The vapor pressures of pure methanol and pure water at this temperature are 256 torr and 55.3 torr, respectively. Is the solution ideal? If not, what can you say about the relative strengths of the solute-solvent interactions compared to the solute-solute and solvent-solvent interactions?

Water softeners often replace calcium ions in hard water with sodium ions. Because sodium compounds are soluble, the presence of sodium ions in water does not cause the white, scaly residues caused by calcium ions. However, calcium is more beneficial to human health than sodium because calcium is a necessary part of the human diet, while high levels of sodium intake are linked to increases in blood pressure. The U.S. Food and Drug Administration (FDA) recommends that adults ingest less than 2.4 g of sodium per day. How many liters of softened water, containing a sodium concentration of 0.050% sodium by mass, does a person have to consume to exceed the FDA recommendation? (Assume a water density of 1.0 g >mL.)

Scuba divers breathing air at increased pressure can suffer from oxygen toxicity-too much oxygen in their bloodstream-when the partial pressure of oxygen exceeds about 1.4 atm. What happens to the amount of oxygen in a diver"s bloodstream when he or she breathes oxygen at elevated pressures? How can this be reversed?

Silver nitrate solutions are used to plate silver onto other metals. What is the maximum amount of silver (in grams) that can be plated out of 4.8 L of an AgNO3 solution containing 3.4% Ag by mass? Assume that the density of the solution is 1.01 g >mL.

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.