Chapter 8: Problem 26
The following groups are found in some organic molecules. Which are hydrophilic and which are hydrophobic: (a) \(-\mathrm{OH}_{;}\)(b) \(-\mathrm{CH}_{2} \mathrm{CH}_{3}\); (c) \(-\mathrm{CONH}_{2}\); (d) \(-\mathrm{Cl}\) ?
Short Answer
Expert verified
Hydrophilic groups: \(a) -\mathrm{OH}\, \(c) -\mathrm{CONH}_{2}\, \(d) -\mathrm{Cl}\. Hydrophobic group: \(b) -\mathrm{CH}_{2} \mathrm{CH}_{3}\.
Step by step solution
01
Understand the Terms
Hydrophilic groups have an affinity for water and typically contain polar or charged atoms that can form hydrogen bonds with water. Hydrophobic groups repel water and are typically nonpolar, lacking any charge that would attract water molecules.
02
Evaluate Group (a) \( -\mathrm{OH} \)
The hydroxyl (\(-\mathrm{OH}\)) group contains a polar O-H bond, making it capable of forming hydrogen bonds with water. Therefore, the hydroxyl group is hydrophilic.
03
Evaluate Group (b) \( -\mathrm{CH}_{2} \mathrm{CH}_{3} \)
The ethyl (\(-\mathrm{CH}_{2} \mathrm{CH}_{3}\)) group is made of carbons and hydrogens, which are nonpolar. This group cannot interact significantly with water, making it hydrophobic.
04
Evaluate Group (c) \( -\mathrm{CONH}_{2} \)
The amide (\(-\mathrm{CONH}_{2}\)) group has a polar C=O bond and an N-H bond. It can form hydrogen bonds due to the presence of these polar bonds and therefore, is hydrophilic.
05
Evaluate Group (d) \( -\mathrm{Cl} \)
The chloride (\(-\mathrm{Cl}\)) group has a polarized bond given the significant difference in electronegativity between chlorine and carbon. Thus, it can interact with water, making it hydrophilic.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Polar and Nonpolar Molecules
When it comes to molecules, understanding the difference between polar and nonpolar ones is crucial. Polar molecules, like water, have an unequal distribution of electrical charges, meaning one end of the molecule is partially negative, while the other is partially positive. Why does this happen? It all boils down to electronegativity, which is how strongly an atom attracts electrons in a bond. Polar molecules arise when atoms with different electronegativities come together and electrons aren't shared equally.
Nonpolar molecules, on the other hand, have a pretty even distribution of electrical charges due to the atoms sharing their electrons equally or due to symmetrical molecular structures. This occurs when the atoms have similar electronegativities or are identical. Common nonpolar molecules are often hydrocarbons—molecules composed solely of hydrogen and carbon, like ethane and methane. So, when students ask why oil and water don't mix, it's because oil is nonpolar and water is polar; they're incompatible.
Nonpolar molecules, on the other hand, have a pretty even distribution of electrical charges due to the atoms sharing their electrons equally or due to symmetrical molecular structures. This occurs when the atoms have similar electronegativities or are identical. Common nonpolar molecules are often hydrocarbons—molecules composed solely of hydrogen and carbon, like ethane and methane. So, when students ask why oil and water don't mix, it's because oil is nonpolar and water is polar; they're incompatible.
Hydrogen Bonding
Now, let's dive into hydrogen bonding, which is like the friendly handshake of the molecular world. It's a type of attraction that's weaker than ionic or covalent bonds but stronger than most other types of intermolecular forces. This bond happens when a hydrogen atom from one molecule, already covalently bonded to a highly electronegative atom (like oxygen or nitrogen), gets attracted to another electronegative atom from a different molecule.
Hydrogen bonds are the secret behind water's high boiling point and its ability to dissolve so many substances. They're also key players in the structure of DNA and proteins. Whenever students see groups like -OH or -NH in a molecule, those are flag bearers for potential hydrogen bonding, bringing hydrophilicity into the mix because they can cozy up to water molecules quite nicely.
Hydrogen bonds are the secret behind water's high boiling point and its ability to dissolve so many substances. They're also key players in the structure of DNA and proteins. Whenever students see groups like -OH or -NH in a molecule, those are flag bearers for potential hydrogen bonding, bringing hydrophilicity into the mix because they can cozy up to water molecules quite nicely.
Organic Chemistry Functional Groups
In the world of organic chemistry, functional groups are the highlight that dictates a molecule's properties and reactions. Think of them as specific groups of atoms within molecules that have their unique characteristic behavior, no matter the size of the molecule they're a part of. There's quite the lineup: from hydroxyl groups (-OH), which bring a touch of polarity, to carbonyl groups (C=O) in ketones and aldehydes that are like reactive hot spots in a molecule.
Each functional group has its own set of properties: alcohols are usually hydrophilic due to the -OH group, ethers are more on the neutral side, and amines (-NH2) can toggle between being hydrophilic or hydrophobic depending on the environment. Understanding these functional groups is like having a cheat sheet for predicting how a molecule will behave, especially in various solvents or during chemical reactions.
Each functional group has its own set of properties: alcohols are usually hydrophilic due to the -OH group, ethers are more on the neutral side, and amines (-NH2) can toggle between being hydrophilic or hydrophobic depending on the environment. Understanding these functional groups is like having a cheat sheet for predicting how a molecule will behave, especially in various solvents or during chemical reactions.
Chemical Polarity
Chemical polarity is the final piece of our molecular puzzle. It's the feature that decides if a molecule will be social (mixing with water) or a loner (repelling water). A polar molecule like ammonia (NH3) loves to hobnob with water molecules because it has a lopsided distribution of charge that makes it easy to form hydrogen bonds. On the flip side, nonpolar molecules like oil keep to themselves because their evenly shared electrons don't offer the water anything to hold onto.
Polarity affects everything from melting and boiling points to solubility and reactivity. A chemist's tip: polar molecules usually have polar bonds (differences in electronegativity), and might have asymmetrical shapes that prevent charge cancellation. Think of polarity as a molecular personality trait—it can make a molecule the life of the party (soluble in water) or a wallflower (insoluble in water).
Polarity affects everything from melting and boiling points to solubility and reactivity. A chemist's tip: polar molecules usually have polar bonds (differences in electronegativity), and might have asymmetrical shapes that prevent charge cancellation. Think of polarity as a molecular personality trait—it can make a molecule the life of the party (soluble in water) or a wallflower (insoluble in water).