Chapter 3, Problem 3.61P

Answer each question about oxycodone, a narcotic analgesic used for severe pain.

a. Identify the functional groups in oxycodone.

b. Classify any alcohol, amide or amine as $1°$, $2°$ or $3^{°}$.

c. Which proton is most acidic?

d. Which site is most basic?

e. What is the hybridization of the N atom?

f. How many $s{p}^2$ hybridized C atoms does oxycodone contain?

Interpretation Introduction

(a)

Interpretation: The functional groups present in the given compound, oxycodone are to be identified.

Concept introduction: An atom or a group of atoms that shows characteristic physical and chemical properties are collectively known as functional groups. The functional group is the most reactive part present in the molecule. The main functional groups are $\text{OH}$ (alcoholic group), $\text{COOH(carboxylic}\text{group)}$, $\text{CHO}\left(\text{aldehydic}\text{group}\right)$ and $\text{C=O}\left(\text{ketonic}\text{group}\right)$.

Answer to Problem 3.61P

The functional groups present in the given compound, oxycodone are shown below.

Explanation of Solution

The functional groups present in the given compound, oxycodone are shown as,

Figure 1

Thus, there are total five functional groups present in oxycodone which are ether group, amine group, alcoholic group, ketonic group and aromatic ring as highlighted above.

Conclusion

There are total five functional groups present in oxycodone which are ether group, amine group, alcoholic group, ketonic group and aromatic ring.

Interpretation Introduction

(b)

Interpretation: The alcohol, amine or amide groups present in the given compound, oxycodone are to be classified as $1^{°}$, $2^{°}$, or $3^{°}$.

Concept introduction: The amine, amide or alcoholic groups are identified as primary $\left(1^{°}\right)$, secondary $\left(2^{°}\right)$ and tertiary $\left(3^{°}\right)$. The primary amine, amide or alcoholic groups are the one in which amine, amide or $\text{OH}$ groups are attached to that carbon atom which is bonded with one carbon atom only. The secondary amine, amide or alcoholic groups are the one in which amine, amide or $\text{OH}$ groups are attached to that carbon atom which is bonded with two carbon atoms. The tertiary amine, amide or alcoholic groups are the one in which amine, amide or $\text{OH}$ group are attached to that carbon atom which is bonded with three carbon atoms.

Answer to Problem 3.61P

The classification of alcohol, amine or amide groups present in the given compound, oxycodone as $1^{°}$, $2^{°}$, or $3^{°}$ is shown below.

Explanation of Solution

The classification alcohol, amine or amide groups present in the given compound, oxycodone are shown as,

Figure 2

The given compound consists of one tertiary amine and one tertiary alcohol.

Conclusion

The given compound, oxycodone consists of one tertiary amine and one tertiary alcohol.

Interpretation Introduction

(c)

Interpretation: The most acidic proton present in the given compound, oxycodone is to be labeled.

Concept introduction: The most acidic hydrogen $\left(\text{H}\right)$ atom or proton is the one which can be easily eliminated from the molecule. This higher acidity of $\text{H-atom}$ is dependent upon the electronegativity of the functional groups that are bonded with carbon atom containing hydrogen. The elimination of a proton leads to the formation of a conjugate base. The higher stability of the conjugate base corresponds to the higher acidity of the proton.

Answer to Problem 3.61P

The labeling of the most acidic proton present in the given compound, oxycodone is shown below.

Explanation of Solution

The labeling of the most acidic proton present in the given compound, oxycodone is shown as,

Figure 3

The electronegativity increases while moving left to right in the period. Thus, oxygen is more electronegative than nitrogen atom as it is located at the extreme right position. According to the structure of oxycodone, hydrogen atom that is bonded with oxygen atom is the most acidic one because oxygen is more electronegative than nitrogen atom. The higher electronegativity corresponds to the greater acidic character of hydrogen atom attached to the electronegative atom.

Conclusion

The labeling of the most acidic proton present in the given compound, oxycodone is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The most basic site in the compound oxycodone is to be labeled.

Concept introduction: According to Bronsted-Lowry theory, the species that easily tends to accept the proton is known as base and the species that easily donate the proton is known as acid. The high delocalization of electron pair corresponds to the high basic character of the atom.

Answer to Problem 3.61P

The labeling of the most basic site in the compound oxycodone is shown below.

Explanation of Solution

The labeling of the most basic site in the compound oxycodone is shown as,

Figure 4

According to the structure of oxycodone, the site at which amine group is present is the most basic site because in amines, the pair of electrons over nitrogen atom gets highly delocalized. Hence, the most basic site is present at tertiary amine.

Conclusion

The labeling of the most basic site in the compound oxycodone is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The hybridization of $\text{N}$-atom in oxycodone is to be identified.

Concept introduction: The procedure of intermixing of the atomic orbitals in an atom is known hybridization. This intermixing of the atomic orbitals is used to form a set of new atomic orbital with different geometry.

Answer to Problem 3.61P

The hybridization of $\text{N}$-atom present in oxycodone is shown below.

Explanation of Solution

The hybridization of $\text{N}$-atom in oxycodone is shown as,

Figure 5

As it is clearly seen that nitrogen atom present in oxycodone possesses three bond pairs and one lone pair. This type of bonding indicates that N-atom in oxycodone is $s{p}^3$ hybridized.

Conclusion

The hybridization of $\text{N}$-atom present in oxycodone is $s{p}^3$.

Interpretation Introduction

(f)

Interpretation: The total number of $s{p}^2$ hybridized C atoms contained by oxycodone is to be identified.

Concept introduction: The procedure of intermixing of the atomic orbitals in an atom is known hybridization. This intermixing of the atomic orbitals is used to form a set of new atomic orbital with different geometry.

Answer to Problem 3.61P

There are total seven $s{p}^2$ hybridized C atoms contained by oxycodone as shown below.

Explanation of Solution

The total number of $s{p}^2$ hybridized C atoms contained by oxycodone is shown as,

Figure 6

There are total seven $s{p}^2$ hybridized C atoms possessed by oxycodone.

Conclusion

The total number of $s{p}^2$ hybridized C atoms contained by oxycodone is $7$.