Chapter 14, Problem 14.29SP

Write structural formulas for the following compounds.

1. a. ethyl isopropyl ether
2. b. di-n-butyl ether
3. c. 2-ethoxyoctane
4. d. divinyl ether
5. e. allyl methyl ether
6. f. cyclohexene oxide
7. g. cis-2,3-epoxyhexane
8. h. (2R, 3S)-2-methoxypentan-3-ol
9. i. trans-2,3-dimethyloxirane

Interpretation Introduction

Interpretation:

The structure formula for the given compound is to be drawn.

Concept introduction:

An organic compound where an oxygen atom is attached to two alkyl or aryl groups is known as ether. The general formula of ethers is $\text{R}-\text{O}-{\text{R}}^{\text{'}}$. Ethers are classified in two categories: simple or symmetrical ethers and mixed or unsymmetrical ethers.

Answer to Problem 14.29SP

The structure of ethyl isopropyl ether is shown in Figure 1.

Explanation of Solution

The given compound is ethyl isopropyl ether. The root name isopropyl signifies three carbon atoms in a chain. Ethyl and isopropyl are the groups attached to an oxygen atom. The structure of ethyl isopropyl ether is shown below.

Figure 1

Interpretation Introduction

Interpretation:

The structure formula for the given compound is to be drawn.

Concept introduction:

An organic compound where an oxygen atom is attached to two alkyl or aryl groups is known as ether. The general formula of ethers is $\text{R}-\text{O}-{\text{R}}^{\text{'}}$. Ethers are classified in two categories: simple or symmetrical ethers and mixed or unsymmetrical ethers.

Answer to Problem 14.29SP

The structure of di-n-butyl ether is shown in Figure 2.

Explanation of Solution

The given compound is di-n-butyl ether. The root name butyl signifies four carbon atoms in a chain and di-n-butyl indicates that two butyl groups are attached to an oxygen atom. The structure of di-n-butyl ether is shown below.

Figure 2

Interpretation Introduction

Interpretation:

The structure formula for the given compound is to be drawn.

Concept introduction:

An organic compound where an oxygen atom is attached to two alkyl or aryl groups is known as ether. The general formula of ethers is $\text{R}-\text{O}-{\text{R}}^{\text{'}}$. Ethers are classified in two categories: simple or symmetrical ethers and mixed or unsymmetrical ethers.

Answer to Problem 14.29SP

The structure of 2-ethoxyoctane is shown in Figure 3.

Explanation of Solution

The given compound is 2-ethoxyoctane. The root octane signifies eight carbon atoms in a chain and 2-ethoxy shows that ethoxy group is present at second carbon atom of a chain. The structure of 2-ethoxyoctane is shown below.

Figure 3

Interpretation Introduction

Interpretation:

The structure formula for the given compound is to be drawn.

Concept introduction:

An organic compound where an oxygen atom is attached to two alkyl or aryl groups is known as ether. The general formula of ethers is $\text{R}-\text{O}-{\text{R}}^{\text{'}}$. Ethers are classified in two categories: simple or symmetrical ethers and mixed or unsymmetrical ethers.

Answer to Problem 14.29SP

The structure of divinyl ether is shown in Figure 4.

Explanation of Solution

The given compound is divinyl ether. The Vinyl group is the functional group having a formula $-\text{CH}={\text{CH}}_{\text{2}}$. In divinyl ether, two vinyl groups are attached to an oxygen atom. The structure of divinyl ether is shown below.

Figure 4

Interpretation Introduction

Interpretation:

The structure formula for the given compound is to be drawn.

Concept introduction:

An organic compound where an oxygen atom is attached to two alkyl or aryl groups is known as ether. The general formula of ethers is $\text{R}-\text{O}-{\text{R}}^{\text{'}}$. Ethers are classified in two categories: simple or symmetrical ethers and mixed or unsymmetrical ethers.

Answer to Problem 14.29SP

The structure of allyl methyl ether is shown in Figure 5.

Explanation of Solution

The given compound is allyl methyl ether. An allyl group is used as a substituent and has a formula of ${}_{\text{2}}\text{HC}=\text{CH}-{\text{CH}}_{\text{2}}\text{R}$. In allyl methyl ether, allyl and methyl groups are attached to an oxygen atom. The structure of allyl methyl ether is shown below.

Figure 5

Interpretation Introduction

Interpretation:

The structure formula for the given compound is to be drawn.

Concept introduction:

An organic compound where an oxygen atom is attached to two alkyl or aryl groups is known as ether. The general formula of ethers is $\text{R}-\text{O}-{\text{R}}^{\text{'}}$. Ethers are classified in two categories: simple or symmetrical ethers and mixed or unsymmetrical ethers.

Answer to Problem 14.29SP

The structure of cyclohexene oxide is shown in Figure 6.

Explanation of Solution

The given compound is cyclohexene oxide. The root name cyclohexene signifies six carbon atoms in a ring and oxide indicated the presence of epoxide ring. The structure of cyclohexene oxide is shown below.

Figure 6

Interpretation Introduction

Interpretation:

The structure formula for the given compound is to be drawn.

Concept introduction:

An organic compound where an oxygen atom is attached to two alkyl or aryl groups is known as ether. The general formula of ethers is $\text{R}-\text{O}-{\text{R}}^{\text{'}}$. Ethers are classified in two categories: simple or symmetrical ethers and mixed or unsymmetrical ethers.

Answer to Problem 14.29SP

The structure of $\text{cis-2,3-epoxyhexane}$ is shown in Figure 7.

Explanation of Solution

The given compound is $\text{cis-2,3-epoxyhexane}$. The root name epoxyhexane signifies six carbon atoms in a chain and an epoxide ring to which hydrogen atoms are in cis configuration. The structure of $\text{cis-2,3-epoxyhexane}$ is shown below.

Figure 7

Interpretation Introduction

Interpretation:

The structure formula for the given compound is to be drawn.

Concept introduction:

An organic compound where an oxygen atom is attached to two alkyl or aryl groups is known as ether. The general formula of ethers is $\text{R}-\text{O}-{\text{R}}^{\text{'}}$. Ethers are classified in two categories: simple or symmetrical ethers and mixed or unsymmetrical ethers.

Answer to Problem 14.29SP

The structure of $\left(2R,3S\right)\text{-2-methoxypentan-3-ol}$ is shown in Figure 8.

Explanation of Solution

The given compound is $\left(2R,3S\right)\text{-2-methoxypentan-3-ol}$. The root name $\text{pentan}$ signifies five carbon atoms in a chain. Two methoxy and $\text{3-ol}$ indicates the presence of methoxy group at second carbon atom and hydroxyl group at third carbon atom respectively.

According to Fisher projection, $\left(2R,3S\right)$ shows that the configuration of second carbon is $R$ and of third carbon is $S$. An asymmetric carbon atom is represented as a cross in Fisher projection. The carbon chain is kept along the vertical line. The groups attached asymmetric carbon atoms are arranged according to their configuration in Fisher projection.

For $R$ configuration, first priority is given to methoxy group, then $\text{C3}$, then $-{\text{CH}}_3$ group followed by hydrogen atom. The direction is anticlockwise but hydrogen is present in horizontal line. Therefore, the configuration is $R$. Similarly, for $S$ configuration first priority is given to hydroxyl group, then, then $\text{C2}$ $-{\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}$ group followed by hydrogen atom. The direction is anticlockwise but hydrogen is present in horizontal line. Therefore, the configuration is $S$.

The structure of $\left(2R,3S\right)\text{-2-methoxypentan-3-ol}$ is shown below.

Figure 8

Interpretation Introduction

Interpretation:

The structure formula for the given compound is to be drawn.

Concept introduction:

An organic compound where an oxygen atom is attached to two alkyl or aryl groups is known as ether. The general formula of ethers is $\text{R}-\text{O}-{\text{R}}^{\text{'}}$. Ethers are classified in two categories: simple or symmetrical ethers and mixed or unsymmetrical ethers.

Answer to Problem 14.29SP

The structure of $\text{trans-2,3-dimethyloxirane}$ is shown in Figure 9.

Explanation of Solution

The given compound is $\text{trans-2,3-dimethyloxirane}$. The root name oxirane signifies the presence of epoxide ring. The number $\text{2,3-dimethyl}$ indicates the presence of two methyl groups at second and third carbon atoms respectively in trans configuration. The structure of $\text{trans-2,3-dimethyloxirane}$ is shown below.

Figure 9