Which of the preceding compounds forms hydrogen bonds with a solvent such as ethanol?1. CH3CH2OCH2CH2OH2. CH3CH2N(CH3)23. CH3CH2CH2CH2Br

Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

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Bruice 8th Edition

Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

Problem 33b(1,2,3)

Chapter 4, Problem 33b(1,2,3)

Which of the preceding compounds forms hydrogen bonds with a solvent such as ethanol?
1. CH₃CH₂OCH₂CH₂OH
2. CH₃CH₂N(CH₃)₂
3. CH₃CH₂CH₂CH₂Br

Verified step by step guidance

Step 1: Understand the concept of hydrogen bonding. Hydrogen bonds occur when a hydrogen atom is covalently bonded to a highly electronegative atom (such as oxygen, nitrogen, or fluorine) and interacts with another electronegative atom in a nearby molecule.

Step 2: Analyze the structure of compound 1 (CH₃CH₂OCH₂CH₂OH). This molecule contains an -OH group, which has a hydrogen atom directly bonded to an electronegative oxygen atom. This makes it capable of forming hydrogen bonds with ethanol.

Step 3: Analyze the structure of compound 2 (CH₃CH₂N(CH₃)₂). The nitrogen atom is electronegative, but there are no hydrogen atoms directly bonded to it. Therefore, this compound cannot form hydrogen bonds with ethanol.

Step 4: Analyze the structure of compound 3 (CH₃CH₂CH₂CH₂Br). Bromine is electronegative, but similar to compound 2, there are no hydrogen atoms directly bonded to it. Thus, this compound cannot form hydrogen bonds with ethanol.

Step 5: Conclude that compound 1 (CH₃CH₂OCH₂CH₂OH) is the only compound among the three that can form hydrogen bonds with ethanol due to the presence of the -OH group.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Hydrogen Bonding

Hydrogen bonding is a type of intermolecular force that occurs when a hydrogen atom covalently bonded to a highly electronegative atom, such as oxygen or nitrogen, interacts with another electronegative atom. This interaction is crucial for the solubility of compounds in polar solvents like ethanol, as it enhances the attraction between the solute and solvent molecules.

Polarity of Molecules

Polarity refers to the distribution of electrical charge over the atoms in a molecule. Polar molecules, which have a significant difference in electronegativity between their atoms, can interact favorably with polar solvents like ethanol. Understanding the polarity of the given compounds helps predict their ability to form hydrogen bonds with ethanol.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of the question, identifying functional groups such as hydroxyl (-OH) in CH3CH2OCH2CH2OH or amine (-NH) in CH3CH2N(CH3)2 is essential, as these groups can participate in hydrogen bonding with ethanol.

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