Chapter 9, Problem 9.1P

Label each ether and alcohol in brevenal, a marine natural product. Classify each alcohol as $1^{\text{ο}},2^{\text{ο}},\text{or}{3}^{\text{ο}}$.

Interpretation Introduction

Interpretation: Each ether and alcohol in brevenal is to be labeled and each alcohol is to be classified as $1^{\text{°}},2^{\text{°}},\text{or}3\text{°}$.

Concept introduction: Alcohols and ethers are the functional groups that involve $\text{C}-\text{O}$, $\text{σ}$ bonds. Alcohols involve a hydroxyl group $\left(-\text{OH}\right)$ bonded to an $s{p}^3$ hybridized $\text{C}$ atom. They are classified as $1\text{°},2\text{°},\text{or}3\text{°}$ on the basis of number of $\text{C}$ atoms bonded to the carbon with the hydroxyl group. Ethers have two aryl or alkyl groups bonded to an $\text{O}$ atom.

Answer to Problem 9.1P

Each ether and alcohol in brevenal is labeled as shown below.

Explanation of Solution

The structure of brevenal (given compound) is,

Figure 1

Alcohols and ethers are the functional groups that involve $\text{C}-\text{O}$ $\text{σ}$ bonds. Alcohols involve a hydroxyl group $\left(-\text{OH}\right)$ bonded to an $s{p}^3$ hybridized $\text{C}$ atom. Ethers have two aryl or alkyl groups bonded to an $\text{O}$ atom. Thus, each ether and alcohol in brevenal is labeled as,

Figure 2

Alcohols are classified as $1\text{°},2\text{°},\text{or}3\text{°}$ on the basis of number of $\text{C}$ atoms bonded to the carbon atom with the hydroxyl group. In Figure 2, there are two alcohols. These alcohols are labeled with A and B in Figure 3.

Figure 3

In Figure 3, the carbon atom of alcohol (A) is bonded to two $\text{C}$ atoms and the carbon atom of alcohol (B) is bonded to three $\text{C}$ atoms.

If the number of carbon atom bonded to the carbon atom with the hydroxyl group is one, then it is classified as $1\text{°}$ alcohol. If the number of carbon atom bonded to the carbon atom with the hydroxyl group is two, then it is classified as $2\text{°}$ alcohol. If the number of carbon atom bonded to the carbon atom with the hydroxyl group is three, then it is classified as $3\text{°}$ alcohol.

Thus, each alcohol in brevenal is classified as,

Figure 4

Conclusion

Each ether and alcohol in brevenal is labeled in Figure 2.