The following structures are constitutional isomers with the formula C4H100. Rank them in order of increasing boiling point, and provide an explanation. он HO. n-butanol HO sec-butanol diethyl ether tert-butanol
The following structures are constitutional isomers with the formula C4H100. Rank them in order of increasing boiling point, and provide an explanation. он HO. n-butanol HO sec-butanol diethyl ether tert-butanol
Chemistry: The Molecular Science
5th Edition
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:John W. Moore, Conrad L. Stanitski
Chapter2: Chemical Compounds
Section2.9: Organic Molecular Compounds
Problem 2.12E
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![### Order of Increasing Boiling Point for C₄H₁₀O Isomers
The following structures represent constitutional isomers with the chemical formula C₄H₁₀O. Each isomer has distinct properties which can influence their boiling points. Below we will rank them in order of increasing boiling point and provide an explanation for the ranking based on their molecular structure and intermolecular forces.
#### Isomers:
1. **n-butanol**
![n-butanol](https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/CID/263/PNG)
This structure consists of a straight-chain four-carbon alcohol.
2. **sec-butanol**
![sec-butanol](https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/CID/6562/PNG)
This isomer has a secondary alcohol, with the OH group attached to the second carbon in a straight chain.
3. **diethyl ether**
![diethyl ether](https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/CID/3283/PNG)
This is an ether with an oxygen atom connected to two ethyl groups.
4. **tert-butanol**
![tert-butanol](https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/CID/6386/PNG)
In this isomer, the OH group is attached to a tertiary carbon atom, where the carbon with the OH group is connected to three other carbon atoms.
### Ranking by Increasing Boiling Point:
1. **Diethyl ether**:
- Boiling Point: ~34.6°C
- Explanation: Ethers generally have lower boiling points compared to alcohols of similar molecular weight due to weaker intermolecular forces. Diethyl ether mainly experiences dipole-dipole interactions and van der Waals forces.
2. **tert-Butanol**:
- Boiling Point: ~82°C
- Explanation: As a tertiary alcohol, tert-butanol cannot form as many hydrogen bonds as primary and secondary alcohols, leading to a lower boiling point compared to n-butanol and sec-butanol.
3. **sec-Butanol**:
- Boiling Point: ~99.5°C
- Explanation: Secondary alcohols like sec-butanol have a higher](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F9c9849aa-211e-4bc0-b610-ffe665c6b4be%2F813e8c25-107b-47f0-9639-fe93f8e36212%2Fvdebaj5_processed.png&w=3840&q=75)
Transcribed Image Text:### Order of Increasing Boiling Point for C₄H₁₀O Isomers
The following structures represent constitutional isomers with the chemical formula C₄H₁₀O. Each isomer has distinct properties which can influence their boiling points. Below we will rank them in order of increasing boiling point and provide an explanation for the ranking based on their molecular structure and intermolecular forces.
#### Isomers:
1. **n-butanol**
![n-butanol](https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/CID/263/PNG)
This structure consists of a straight-chain four-carbon alcohol.
2. **sec-butanol**
![sec-butanol](https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/CID/6562/PNG)
This isomer has a secondary alcohol, with the OH group attached to the second carbon in a straight chain.
3. **diethyl ether**
![diethyl ether](https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/CID/3283/PNG)
This is an ether with an oxygen atom connected to two ethyl groups.
4. **tert-butanol**
![tert-butanol](https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/CID/6386/PNG)
In this isomer, the OH group is attached to a tertiary carbon atom, where the carbon with the OH group is connected to three other carbon atoms.
### Ranking by Increasing Boiling Point:
1. **Diethyl ether**:
- Boiling Point: ~34.6°C
- Explanation: Ethers generally have lower boiling points compared to alcohols of similar molecular weight due to weaker intermolecular forces. Diethyl ether mainly experiences dipole-dipole interactions and van der Waals forces.
2. **tert-Butanol**:
- Boiling Point: ~82°C
- Explanation: As a tertiary alcohol, tert-butanol cannot form as many hydrogen bonds as primary and secondary alcohols, leading to a lower boiling point compared to n-butanol and sec-butanol.
3. **sec-Butanol**:
- Boiling Point: ~99.5°C
- Explanation: Secondary alcohols like sec-butanol have a higher
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