Answer the following questions by referring to the...

Answer the following questions by referring to the ball-and-stick model of fentanyl, a potent narcotic analgesic used in surgical procedures. a. Identify the functional groups. b. Label the most acidic proton. c. Label the most basic atom. d. What types of intermolecular forces are present between two molecules of fentanyl? e. Draw an isomer predicted to have a higher boiling point. f. Which sites in the molecule can hydrogen bond to water? g. Label all electrophilic carbons.

Answer the following questions by referring to the ball-and-stick model of fentanyl, a potent narcotic analgesic used in surgical procedures.
a. Identify the functional groups.
b. Label the most acidic proton.
c. Label the most basic atom.
d. What types of intermolecular forces are present between two molecules of fentanyl?
e. Draw an isomer predicted to have a higher boiling point.
f. Which sites in the molecule can hydrogen bond to water?
g. Label all electrophilic carbons.

Key Concepts

Functional Groups

Functional groups are specific clusters of atoms within molecules that have characteristic chemical behaviors and reactivities. They serve as the reactive centers responsible for the bulk of a molecule's chemical properties, influencing polarity, acidity, basicity, and the types of reactions the molecule can partake in.

Acidic and Basic Sites

Acidic protons and basic atoms within a molecule represent the sites that can donate or accept protons, respectively. The acidity is often determined by the support of the resulting anion through resonance or inductive effects, while basicity is influenced by the availability of a lone pair of electrons to accept a proton.

Intermolecular Forces

Intermolecular forces are the non-covalent interactions that occur between molecules, including hydrogen bonding, dipole-dipole interactions, and van der Waals forces. These forces determine many physical properties of compounds, such as boiling and melting points, solubility, and viscosity.

Structural Isomerism

Structural isomerism involves molecules that have the same molecular formula but different arrangements of atoms. These differences can significantly affect physical properties like boiling points, as varying placements of functional groups and overall molecular geometry alter the strength and type of intermolecular interactions.

Hydrogen Bonding

Hydrogen bonding is a specific type of dipole-dipole interaction that occurs when a hydrogen atom bonded to a highly electronegative atom such as oxygen or nitrogen interacts with a lone pair of electrons on another electronegative atom. This type of interaction contributes to enhanced solubility in polar solvents and affects the physical properties like boiling and melting points.

Electrophilic Sites

Electrophilic sites in a molecule are regions that are electron-deficient and can accept electrons from nucleophiles during chemical reactions. These sites are crucial in many organic reactions, guiding how and where a reaction will take place based on the distribution of electron density in the molecule.

Transcript

00:02 The following are functional groups within this compound.

00:05 Here we have an amid.

00:07 A carbonyl attached to a nitrogen is an amid.

00:10 This is a phenyl group.

00:13 This is also a phenyl group.

00:15 If you add in the benzylic carbon right next to it, so a ch2 next to it, this whole group is called a benzil group, phenyl, benzo.

00:26 This is an amine, and the rest is just an aliphatic hydrocarbon chain.

00:31 The most acidic hydrogen is going to be the one of the two directly attached to the alpha carbonial.

00:42 So alpha, meaning just one away from functional group.

00:45 The reason that hydrogen is so acidic is because if we draw the conjugate base, we will see that there is a resonance structure that stabilizes the anion.

00:57 So that hydrogen has a p .k of pretty close to 25, 28.

01:02 It depends you ask, but probably close.

01:03 To 28.

01:06 Label the most basic atom? well, that is going to be this nitrogen because it has a lone pair of electrons it can use to attack.

01:16 This nitrogen does as well.

01:18 However, the lone pair is caught up in resonance of the amid, so it is not as basic.

01:25 What type of intermolecular forces are present between two molecules of fentanyl, so not intra, but intermolecular forces? so we don't have any hydrogen bonding because we don't have any hydrogens attached to nitrogen or oxygen.

01:40 So the strongest forces we're going to have are dipole forces because there are definitely bonds that have dipole moments.

01:47 So dipole, dipole, and then as every compound has, london dispersion forces.

01:53 Draw an isomer predicted to have a higher boiling point...

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