An N-HNN hydrogen bond is weaker thiun an \(\mathrm{O}-\mathrm{H}-\mathrm{O}\) hydrogen bond because the difference in electronegativity hetween nitrogen and hydrogen \((3.0\) \(2.1=0.9)\) is less than that between oxygen and hydrogen \((3.5-2.1-1.4)\). The ef= fect of intermolecular hyvlrogen bonding can be illustrated by comparing the boiling points of methylamine and methamol. Both are polar molecules and interact in the pure liquid hy hydroggen bonding. Because hydrogen bonding is stronger in methanol than in methylamine, methanol has the: higher boiling point.

Short Answer

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Answer: An N-H hydrogen bond is weaker than an O-H hydrogen bond due to the lesser difference in electronegativity. The difference in electronegativity for N-H bond is 0.9 and for O-H bond is 1.4. This greater difference in O-H bond makes it stronger. Consequently, methanol, which contains stronger O-H hydrogen bonds, has a higher boiling point compared to methylamine, as more energy is required to overcome the stronger hydrogen bonds in methanol.

Step by step solution

01

Understand Hydrogen Bonding

Hydrogen bonding occurs when a hydrogen atom is bonded to a more electronegative atom like nitrogen, oxygen, or fluorine, and is attracted to another electronegative atom. The strength of the hydrogen bond depends on the difference in electronegativity between the hydrogen and the other atom.
02

Calculate Electronegativity Differences

Let's calculate the electronegativity difference for both N-H and O-H bonds. Electronegativity of Nitrogen (N) is 3.0, Hydrogen (H) is 2.1, and Oxygen (O) is 3.5. Difference in electronegativity for N-H bond: \(3.0 - 2.1 = 0.9\) Difference in electronegativity for O-H bond: \(3.5 - 2.1 = 1.4\)
03

Compare Bond Strength

Since the electronegativity difference for the O-H bond is greater than the N-H bond (\(1.4 > 0.9\)), it means the O-H bond is stronger as the attraction between the two atoms is greater in O-H bond as compared to N-H bond.
04

Introduce Methylamine and Methanol

Now let's illustrate the effect of intermolecular hydrogen bonding by comparing the boiling points of methylamine (CH3NH2) and methanol (CH3OH). Both of these molecules are polar and interact in the pure liquid state by hydrogen bonding.
05

Compare Hydrogen Bonding Strength

As we have established, hydrogen bonding in methanol (O-H bond) is stronger than in methylamine (N-H bond) due to the greater electronegativity difference.
06

Compare Boiling Points

The stronger hydrogen bonding in methanol results in a higher boiling point than in methylamine. This is because more energy is required to overcome the stronger hydrogen bonds in methanol, making it harder for the molecules to separate and move into the gas phase. To sum up, the N-H hydrogen bond is weaker than the O-H hydrogen bond due to the lesser difference in electronegativity. As a result, methanol, which has stronger hydrogen bonding, has a higher boiling point compared to methylamine.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Electronegativity Difference
Electronegativity represents the tendency of an atom to attract electrons towards itself when bonded in a molecule. It's a fundamental concept in chemistry that helps explain many molecular behaviors, including bond strength and polarity.

When considering hydrogen bonding, the difference in electronegativity between hydrogen and the other atom it's bonded to is crucial. Typically, a greater difference means a stronger pull on the shared electrons, leading to a more polar bond. This polarity is what makes hydrogen bonding possible. In the case of nitrogen and hydrogen, the difference is 0.9, while for oxygen and hydrogen, it's 1.4, signifying a more potent attraction and hence a stronger hydrogen bond in the latter.
Intermolecular Forces
Intermolecular forces are the forces that mediate interaction between molecules, including forces of attraction or repulsion which act between molecules and other types of neighboring particles.

Hydrogen bonds are a type of intermolecular force and are particularly strong because they involve a hydrogen atom bonded to a highly electronegative atom (such as N, O, or F). These forces are essential in determining the physical properties of a substance, like boiling point and melting point. The stronger the intermolecular forces, the more energy is required to overcome these interactions and change the physical state of a substance.
Boiling Point Comparison
Boiling points provide a key insight into the strength of intermolecular forces within a substance. It's the temperature at which the vapor pressure of a liquid equals the external pressure surrounding the liquid, causing the liquid to turn into vapor.

A higher boiling point indicates that more energy is required to break the intermolecular forces. In the context of hydrogen bonds, the stronger these bonds are within a substance, the higher the boiling point will be. Thus, the boiling point is a practical demonstration of the underlying intermolecular interactions, with methanol showcasing a higher boiling point over methylamine due to stronger hydrogen bonds.
Methylamine vs Methanol
Understanding the difference between methylamine (CH3NH2) and methanol (CH3OH) in terms of their boiling points is an excellent demonstration of intermolecular hydrogen bonding. Both compounds have the ability to form hydrogen bonds, yet the key difference lies in the atoms involved.

Methanol contains an O-H bond, which, due to a larger electronegativity difference, leads to stronger hydrogen bonds compared to the N-H bonds in methylamine. This difference results in methanol having a higher boiling point, reflecting the greater energy required to break these stronger interactions in the liquid state before transitioning into a gas.

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Most popular questions from this chapter

Amines are further divided into aliphatic and aromatic amines. In an aliphatic amine, all carbons bonded to nitrogen are derived from alkyl groups; in an aromatic amine, one or more of the groups bonded to nitrogen are aryl groups.

The geometry of a nitrogen atom bonded to three other atoms or groups of atoms is trigonal pyramidal (Section 1.4). The sp, bybridized nitrogen atom is at the apex of the Pyramid, and the three groups bouded to it extend densaward to form the triangular base of the prramid. If we consider the unshared pair of electrons on nitrogen as a foeurth grosp, then the amrangement of "groups" around nitrogen is approximately tetrahedral. Berause of this geoenetry, an ansine with three different groups bonded to nitrogen is chiral and can exist as a pair of enantiomers, as illustrated by the nonsuperporable mirror images of ethyimethylamine. In assigning configuration to these enantiomers, the groxp of lowest prioxity on nitrogen is the unshared pair of electrons.

Like ammonia, all amines are weak bases, and aqueous solutions of amines are basic. The following acid-base reaction between an amine and water is written uxing curved arross to emphasize that, in these proton-transfer reactions, the unshared pair of electrons on nitrogen forms a new covalent bond with hydrogen and displaces hydroxide ion.

Common names for most aliphatic amines are derived by listing the alkyl groups bonded to nitrogen in alphabetical order in one word ending in the suffix awine, that ix, they are named as alkylamines.

Phosphorus, in the sume family as nitrogen, forms trivalent compounds called phosphines, which also have trigonal pyramidal geometry. The activation energy for pyramidal inversion of trivalent phosphorus compounds is considerably greater thin it is for trivalent compounds of nitrogen, with the result that a number of chiral phosphines have been resolved.

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