Question

Draw the Lewis structure for hydroxylamine, \(\mathbf{H}_{2} \mathrm{NOH}\). What is the hybridization for nitrogen and oxygen in this molecule? What orbitals overlap to form the bond between nitrogen and oxygen?

Short answer

Nitrogen and oxygen in hydroxylamine are both \( sp^3 \) hybridized, and the N-O bond is formed by \( sp^3 \) overlap.

Step-by-step solution

Identify Valence Electrons

First, determine the number of valence electrons for each atom in the molecule. Hydrogen (H) has 1 valence electron, nitrogen (N) has 5, and oxygen (O) has 6. Hydroxylamine is composed of two hydrogen atoms, one nitrogen atom, and one oxygen atom, so the total number of valence electrons is calculated as follows: \( 2 \times 1 \text{ (H)} + 5 \text{ (N)} + 6 \text{ (O)} + 1 \text{ (H)} = 14 \).

Skeleton Structure

To draw the skeleton structure of hydroxylamine, connect the nitrogen (N) atom to both the oxygen (O) atom and two hydrogen (H) atoms. Oxygen will also be connected to the remaining hydrogen atom. This forms a chain-like structure: H \( - \) N \( - \) O \( - \) H.

Distribute Electrons

Place a pair of electrons (representing a single bond) between each connected pair of atoms in the molecule from the skeleton structure: H and N, N and O, and O and H. Each bond uses 2 electrons, so 8 electrons are used, leaving 6 electrons to be distributed.

Complete Octet for Oxygen

The oxygen atom needs 8 electrons to complete its octet. It already shares 2 electrons with nitrogen and 2 with hydrogen, so place the remaining 4 valence electrons as lone pairs on oxygen. Now oxygen has 8 electrons (4 in two lone pairs).

Complete Octet for Nitrogen

Next, complete the nitrogen atom's octet. Nitrogen currently shares electrons with hydrogen and oxygen, so place the remaining electrons around nitrogen. Add any available lone pairs to satisfy the octet rule. All the valence electrons (14) are now used.

Determine Hybridization

To determine the hybridization of nitrogen and oxygen, count the regions of electron density around each atom. For nitrogen, there are three regions (2 sigma bonds and 1 lone pair), indicating \( sp^3 \) hybridization. Oxygen also has three regions of electron density (1 sigma bond and 2 lone pairs), which is also \( sp^3 \) hybridized.

Identify Overlapping Orbitals

To determine which orbitals overlap to form the bond between nitrogen and oxygen, note that both nitrogen and oxygen are \( sp^3 \) hybridized. Therefore, the nitrogen-oxygen bond is formed by the overlap of an \( sp^3 \) orbital from nitrogen and an \( sp^3 \) orbital from oxygen.

Key concepts

Valence Electrons

Valence electrons are the outermost electrons of an atom. They play a crucial role in chemical bonding as they are involved in forming bonds. In the case of hydroxylamine, we calculate the total number of valence electrons by adding those from each atom in the molecule:

• Hydrogen (H) has 1 valence electron.
• Nitrogen (N) has 5 valence electrons.
• Oxygen (O) has 6 valence electrons.

Since the molecule contains two hydrogens, one nitrogen, and one oxygen, the total count is:\[ 2\times 1 \text{ (H)} + 5 \text{ (N)} + 6 \text{ (O)} + 1 \text{ (extra H)} = 14 \]These 14 electrons need to be arranged around the atoms to satisfy the bonding needs and octet rule, with attention to which atoms naturally bond with which in order to balance out the electron count effectively.

Hybridization

Hybridization is the mixing of atomic orbitals in an atom to form new hybrid orbitals, which can form sigma and pi bonds with other atoms in a molecule. It defines the molecule's geometry, affecting its chemical reactivity.

In hydroxylamine:

• For Nitrogen (N): The nitrogen atom forms three bonds (two with hydrogen and one with oxygen) and holds one lone pair. This makes for four regions of electron density, indicating an \( sp^3 \) hybridization.
• For Oxygen (O): The oxygen atom in hydroxylamine is bonded to hydrogen and nitrogen and carries two lone pairs, also contributing to four regions of electron density, thus \( sp^3 \) hybridization.

This suggests that each atom achieves a tetrahedral geometry, though actual bond angles may slightly deviate due to the presence of lone pairs, which exert more repulsion than bonded pairs. Understanding hybridization helps to predict molecular shapes, in turn, providing insight into the molecule's physical and chemical properties.

Molecular Orbital Theory

Molecular Orbital Theory (MOT) is an advanced method of explaining the bonding in molecules by considering electrons to be distributed in molecular orbitals that extend over the entire molecule. This theory provides a more sophisticated view of bonding beyond the simple pair-share model of Lewis structures.

In hydroxylamine:

• The N-O bond is formed by the overlap of \( sp^3 \) hybrid orbitals from both nitrogen and oxygen.
• These orbitals specifically create a sigma bond, which is strong and forms the backbone of the molecule.

These interactions are crucial for the stability and shape of the molecule. MOT allows chemists to understand bond strengths, lengths, and the electron distribution that affects how molecules interact with each other in reactions.