/*! 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 15 Propanoic acid and methyl acetat... [FREE SOLUTION] | 91Ó°ÊÓ

91Ó°ÊÓ

Propanoic acid and methyl acetate are constitutional isomers, and both are liquids at room temperature. One of these compounds has a boiling point of \(141^{\circ} \mathrm{C}\) the other has a boiling point of \(57^{\circ} \mathrm{C}\). Which compound has which boiling point? Explain.

Short Answer

Expert verified
Propanoic acid boils at 141°C; methyl acetate boils at 57°C.

Step by step solution

01

Understand the Compounds

Propanoic acid ( CH_3CH_2COOH) is a carboxylic acid, whereas methyl acetate ( CH_3COOCH_3) is an ester. These compounds are constitutional isomers, meaning they share the same molecular formula but have different structures.
02

Identify Intermolecular Forces Involved

Carboxylic acids, like propanoic acid, can form hydrogen bonds due to the presence of hydroxyl (-OH) groups. In contrast, esters, like methyl acetate, have weaker dipole-dipole interactions since they lack the -OH group.
03

Relate Boiling Points to Intermolecular Forces

The boiling point of a substance is directly related to the strength of the intermolecular forces. Higher boiling points signify stronger intermolecular forces. Carboxylic acids typically have higher boiling points than esters because hydrogen bonding is stronger than the dipole-dipole interactions found in esters.
04

Assign Boiling Points

Given that propanoic acid can form hydrogen bonds, it will have the higher boiling point ( 141^{ ext{o}} ext{C}). Methyl acetate, with only dipole-dipole interaction, will have the lower boiling point ( 57^{ ext{o}} ext{C}).

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.

Intermolecular Forces
Intermolecular forces are the attractions between molecules that influence their physical properties, such as boiling and melting points. There are different types of intermolecular forces, including:
  • Van der Waals forces: The weakest type, including dipole-dipole interactions and London dispersion forces.
  • Dipole-dipole interactions: Occur between polar molecules where partial positive and negative charges attract each other.
  • Hydrogen bonding: A special type of dipole-dipole interaction that occurs when hydrogen is directly bonded to electronegative atoms like oxygen, nitrogen, or fluorine.
Intermolecular forces significantly impact boiling points since stronger forces require more energy to overcome. In our example, propanoic acid and methyl acetate experience different forces: hydrogen bonding in propanoic acid versus weaker dipole-dipole forces in methyl acetate.
Hydrogen Bonding
Hydrogen bonding is an essential intermolecular force that strongly influences the properties of molecules. This bond is a specific type of dipole-dipole interaction that occurs when hydrogen is attached to electronegative atoms such as oxygen, nitrogen, or fluorine.

In molecules like carboxylic acids, hydrogen bonding arises because the hydrogen atom is bonded to an oxygen atom, creating a significant difference in electronegativity. This difference causes the hydrogen to develop a positive charge while the oxygen becomes partially negative. The result is an attraction between the hydrogen of one molecule and the oxygen of a neighboring molecule.

Due to hydrogen bonding, substances like propanoic acid show elevated boiling points. This is because the hydrogen bonds need more energy to be broken than weaker dipole-dipole interactions would require. The strength and number of hydrogen bonds in a molecule determine its physical properties and behaviors in chemical reactions.
Carboxylic Acid vs Ester
Carboxylic acids and esters are functional groups within organic chemistry known for their distinct properties. Both groups can have significant effects on boiling points and other chemical behaviors.

Carboxylic acids: These contain a carboxyl ( COOH) group, responsible for their acidic nature. The ability to form hydrogen bonds makes them capable of existing as dimers in the liquid state, leading to high boiling points. For example, propanoic acid has a boiling point of 141^ {o} C due to these strong hydrogen bonds.

Esters: These contain a corboxylate ( COO) group with an adjacent alkyl chain. They lack the hydroxyl group necessary for hydrogen bonding, instead relying on weaker dipole-dipole attractions. As a result, esters like methyl acetate have relatively lower boiling points such as 57^ {o} C.

Both are constitutional isomers, meaning they share the same molecular formula but differ in atomic arrangement and intermolecular forces. This leads to different boiling points and physical properties.
Constitutional Isomers
Constitutional isomers, sometimes known as structural isomers, are compounds with the same molecular formula but different structural arrangements of atoms. This variation in structure leads to differences in physical and chemical properties such as boiling points, solubilities, and reactivities.

For instance, propanoic acid and methyl acetate both feature the formula C_3H_6O_2. However, due to different arrangements of atoms, their properties differ. Propanoic acid has a carboxyl group, enabling hydrogen bonding, while methyl acetate is an ester, which cannot hydrogen bond effectively.

Understanding constitutional isomers helps in predicting the properties and reactions of organic molecules. Knowing that these isomers differ in structure can explain why they behave differently in chemical reactions and why their physical characteristics, such as boiling points, do not align despite having the same chemical makeup.

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

Answer true or false. (a) Fatty acids are long-chain carboxylic acids, with most consisting of between 12 to 20 carbons in an unbranched chain. (b) An unsaturated fatty acid contains one or more carbon-carbon double bonds in its hydrocarbon chain. (c) In most unsaturated fatty acids found in animal fats, vegetable oils, and biological membranes, the cis isomer predominates. (d) In general, unsaturated fatty acids have lower melting points than saturated fatty acids with the same number of carbon atoms. (e) Natural soaps are sodium or potassium salts of fatty acids. (f) Soaps remove grease, oil, and fat stains by incorporating these substances into the nonpolar interior of soap micelles. (g) "Hard water," by definition, is water that contains \(\mathrm{Ca}^{2+}, \mathrm{Mg}^{2+},\) or \(\mathrm{Fe}^{3+}\) ions, all of which react with soap molecules to form water-insoluble salts. (h) The structure of synthetic detergents is patterned after that of natural soaps. (i) The most widely used synthetic detergents are the linear alkylbenzenesulfonates (LAS) (j) Present-day synthetic detergents do not form water-insoluble salts with hard water. (k) Most detergent preparations contain foam stabilizers, a bleach, and optical brighteners (optical bleaches).

Hexanoic (caproic) acid has a solubility in water of about \(1 \mathrm{g} / 100 \mathrm{mL}\) water. Which part of the molecule contributes to water solubility, and which part prevents solubility?

Alcohols, phenols, and carboxylic acids all contain an \(-\) OH group. Which are the strongest acids? Which are the weakest acids?

The following compounds have approximately the same molecular weight: propanoic acid, 1 -butanol, and diethyl ether. Arrange them in order of increasing boiling point.

Calcium oxalate is a major component of kidney stones. Draw a structural formula for this compound.

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.