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Mobile App Chapter 14: Problem 39
Try to construct an aromatic heterocycle in which there is an oxygen and a nitrogen in a neutral sixmembered ring.
Short Answer
Expert verified
1,3-oxazine
Step by step solution
01
- Understanding Aromaticity
A molecule is considered aromatic if it follows Hückel's rule, which states that a planar ring molecule must have \(4n + 2\) π-electrons, where \(n\) is a non-negative integer. Additionally, the molecule must be cyclic, conjugated, and planar.
02
- Identifying a Six-Membered Heterocycle
A six-membered ring containing both an oxygen and a nitrogen must be identified. Possible candidates might include structures with varying positions of the oxygen and nitrogen atoms.
03
- Ensuring Neutrality
The ring must be neutral, meaning that there are no extra charges on any of the atoms within the ring.
04
- Constructing the Molecule
Considering all the previous factors, the molecule pyridine or similar structures should be reviewed. Another possible candidate is oxazine.
05
- Verifying Aromaticity
Ensure that the chosen heterocycle follows Hückel's rule. For a six-membered ring to be aromatic, it needs to have 6 π-electrons (e.g., benzene and other aromatic heterocycles).
06
- Finalizing the Structure
The most suitable candidate that is aromatic and contains both an oxygen and a nitrogen atom in a neutral six-membered ring is 1,3-oxazine. Verify that it has 6 π-electrons and that it is a conjugated, planar molecule.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Hückel's rule
Hückel's rule is a fundamental principle in the study of aromatic compounds. It specifies that for a molecule to be considered aromatic, it must follow the formula \(4n + 2\) π-electrons, where \(n\) is a non-negative integer (e.g., 0, 1, 2). This rule helps in determining the aromaticity of organic molecules.
For instance, if a molecule has 6 π-electrons, it can be aromatic since \(4 \times 1 + 2 = 6\).
This rule applies to planar and cyclic molecules with conjugated π-systems. Each atom in these systems must have a p-orbital available for the electrons to delocalize seamlessly across the ring.
For instance, if a molecule has 6 π-electrons, it can be aromatic since \(4 \times 1 + 2 = 6\).
This rule applies to planar and cyclic molecules with conjugated π-systems. Each atom in these systems must have a p-orbital available for the electrons to delocalize seamlessly across the ring.
Aromaticity
Aromaticity is a property of cyclic (ring-shaped), planar (flat) molecules with a ring of resonance bonds that leads to enhanced stability. To classify a molecule as aromatic, it must fulfill the following:
An example of an aromatic molecule is benzene. Benzene is a six-membered carbon ring that is completely conjugated, planar, and has 6 π-electrons, in accordance with Hückel’s rule. Therefore, it is highly stable.
- It must be cyclic
- It must be planar
- It must have a conjugated π-system
- It must follow Hückel's rule
An example of an aromatic molecule is benzene. Benzene is a six-membered carbon ring that is completely conjugated, planar, and has 6 π-electrons, in accordance with Hückel’s rule. Therefore, it is highly stable.
Six-membered ring
Six-membered rings are common in chemistry, especially for aromatic compounds and heterocycles. These rings can include different atoms such as nitrogen, oxygen, or sulfur along with carbon. The six-membered structure provides a stable configuration that can be seen in many natural and synthetic molecules.
For example, benzene is a purely carbon-based six-membered ring, while pyridine replaces one carbon atom with a nitrogen atom.
In the context of this exercise, the aim is to construct a neutral six-membered ring that includes both oxygen and nitrogen, such as 1,3-oxazine.
For example, benzene is a purely carbon-based six-membered ring, while pyridine replaces one carbon atom with a nitrogen atom.
In the context of this exercise, the aim is to construct a neutral six-membered ring that includes both oxygen and nitrogen, such as 1,3-oxazine.
Neutral heterocycles
Heterocycles are ring structures composed of more than one type of atom. When producing neutral heterocycles, it’s crucial to ensure that the molecule does not carry a net charge. A neutral heterocycle means that there are no additional charges on any of the atoms within the ring.
These structures are chemically significant as they form the backbone of many biological molecules and pharmaceuticals.
In this exercise, the task involves creating a six-membered ring with one nitrogen and one oxygen atom without any charges, leading to the formation of 1,3-oxazine as a neutral heterocycle.
These structures are chemically significant as they form the backbone of many biological molecules and pharmaceuticals.
In this exercise, the task involves creating a six-membered ring with one nitrogen and one oxygen atom without any charges, leading to the formation of 1,3-oxazine as a neutral heterocycle.
1,3-oxazine
1,3-oxazine is a heterocyclic compound that consists of a six-membered ring containing one nitrogen and one oxygen atom at the 1 and 3 positions, respectively. This arrangement creates a compound that obeys Hückel’s rule, making it aromatic.
The molecule has 6 π-electrons contributed by the overlapping p-orbitals of the ring atoms, which allows for great stability. This stability is due to the delocalization of these π-electrons over the entire ring structure.
1,3-oxazine serves various functions in pharmaceutical and organic chemistry, showing its importance as an aromatic compound.
The molecule has 6 π-electrons contributed by the overlapping p-orbitals of the ring atoms, which allows for great stability. This stability is due to the delocalization of these π-electrons over the entire ring structure.
1,3-oxazine serves various functions in pharmaceutical and organic chemistry, showing its importance as an aromatic compound.
