Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 10: Problem 107

Consider two different organic compounds, each with the formula \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O} .\) One of these compounds is a liquid at room conditions and the other is a gas. Write Lewis structures consistent with this observation, and explain your answer. (Hint: The oxygen atom in both structures satisfies the octet rule with two bonds and two lone pairs.)

Short Answer

Expert verified
The two possible structures for the given formula C2H6O are ether (\( \mathrm{CH_3 - O - CH_3} \)) and alcohol (\( \mathrm{CH_3 - CH_2 - OH} \)). The ether compound is a gas at room conditions because it has only weak to moderately strong intermolecular forces (London dispersion forces and dipole-dipole attractions). The alcohol compound is a liquid at room conditions due to the stronger hydrogen bonding in addition to London dispersion forces and dipole-dipole attractions. These differences in intermolecular forces dictate their physical states at room temperature.

Step by step solution

01

Draw possible structures considering the octet rule.

There can be two possible structures for the given formula: 1. An ether (a central oxygen atom connecting two methyl groups): Structure: \( \mathrm{CH_3 - O - CH_3} \) 2. An alcohol (a hydroxyl group connected to an ethyl group): Structure: \( \mathrm{CH_3 - CH_2 - OH} \) Both of these structures follow the octet rule as mentioned in the hint, with oxygen having two bonds and two lone pairs.
02

Identify intermolecular forces in each compound.

Next, we need to look at the types of intermolecular forces present in each of these compounds: 1. Ether: This compound only contains London dispersion forces (LDF) and dipole-dipole attractions due to the slightly polar C-O bond. LDF are weak, and dipole-dipole attractions are moderately strong. 2. Alcohol: This compound contains London dispersion forces, dipole-dipole attractions, as well as hydrogen bonding between the oxygen atom's lone pair and a hydrogen atom from the hydroxyl group in a neighboring molecule. Hydrogen bonding is a relatively strong intermolecular force.
03

Determine the state of the compound at room conditions based on intermolecular forces.

Now, we can reason: 1. Ether: The intermolecular forces in the ether compound are relatively weak compared to the alcohol compound. As a result, the boiling point of the ether will be lower and it will be a gas at room temperature. 2. Alcohol: The presence of hydrogen bonding, which is a strong intermolecular force, leads to a higher boiling point and consequently, the alcohol compound will be a liquid at room conditions.
04

Write the final answer.

The ether compound, \( \mathrm{CH_3 - O - CH_3} \), is a gas at room conditions because it has only weak to moderately strong intermolecular forces (LDF and dipole-dipole attractions). The alcohol compound, \( \mathrm{CH_3 - CH_2 - OH} \), is a liquid at room conditions due to the stronger hydrogen bonding in addition to LDF and dipole-dipole attractions. These differences in intermolecular forces dictate their physical states at room temperature.

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.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

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 an alloy? Explain the differences in structure between substitutional and interstitial alloys. Give an example of each type.

Dry nitrogen gas is bubbled through liquid benzene \(\left(\mathrm{C}_{6} \mathrm{H}_{6}\right)\) at \(20.0^{\circ} \mathrm{C}\). From \(100.0 \mathrm{~L}\) of the gaseous mixture of nitrogen and benzene, \(24.7 \mathrm{~g}\) benzene is condensed by passing the mixture through a trap at a temperature where nitrogen is gaseous and the vapor pressure of benzene is negligible. What is the vapor pressure of benzene at \(20.0{ }^{\circ} \mathrm{C}\) ?

Iridium (Ir) has a face-centered cubic unit cell with an edge length of \(383.3 \mathrm{pm}\). Calculate the density of solid iridium.

A 0.132-mol sample of an unknown semiconducting material with the formula XY has a mass of \(19.0 \mathrm{~g} .\) The element \(\mathrm{X}\) has an electron configuration of \([\mathrm{Kr}] 5 s^{2} 4 d^{10} .\) What is this semiconducting material? A small amount of the \(Y\) atoms in the semiconductor is replaced with an equivalent amount of atoms with an electron configuration of \([\mathrm{Ar}] 4 s^{2} 3 d^{10} 4 p^{5} .\) Does this correspond to n-type or p-type doping?

A common prank on college campuses is to switch the salt and sugar on dining hall tables, which is usually easy because the substances look so much alike. Yet, despite the similarity in their appearance, these two substances differ greatly in their properties, since one is a molecular solid and the other is an ionic solid. How do the properties differ and why?
See all solutions

Recommended explanations on Chemistry Textbooks

Making Measurements

Read Explanation

Physical Chemistry

Read Explanation

Chemistry Branches

Read Explanation

Nuclear Chemistry

Read Explanation

Organic Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation
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.

Sign-up for free