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Ch. 16 - Aromatic Compounds
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Wade 9th EditionCh. 16 - Aromatic Compounds문제 19g,h
16장, 문제 19g,h

Explain why each compound is aromatic, antiaromatic, or nonaromatic.
(g)
(h)

검증된 단계별 안내
1
Step 1: Recall the criteria for aromaticity. A compound is aromatic if it satisfies the following conditions: (a) It is cyclic, (b) It is planar, (c) It has a conjugated π-electron system, and (d) It follows Huckel's rule, which states that the molecule must have (4n + 2) π-electrons, where n is an integer.
Step 2: Analyze compound (g), cytosine. Cytosine is a six-membered ring containing nitrogen and oxygen atoms. The ring is cyclic and planar due to sp2 hybridization of the atoms in the ring. The conjugated π-electron system includes the double bonds and lone pairs on the heteroatoms. Count the π-electrons to determine if it satisfies Huckel's rule.
Step 3: For compound (g), cytosine, consider the lone pairs on the nitrogen and oxygen atoms. Not all lone pairs contribute to aromaticity; only those in conjugation with the π-system are considered. Verify if the total π-electron count is (4n + 2). If it satisfies Huckel's rule, the compound is aromatic; if not, it is nonaromatic or antiaromatic.
Step 4: Analyze compound (h), a six-membered ring with oxygen. The ring is cyclic and planar, and it has alternating double bonds, indicating a conjugated π-electron system. Count the π-electrons, including the lone pair on oxygen, to determine if it satisfies Huckel's rule.
Step 5: For compound (h), verify if the lone pair on oxygen contributes to the conjugated π-system. If the total π-electron count satisfies Huckel's rule, the compound is aromatic. If it does not satisfy Huckel's rule, determine if the compound is antiaromatic (4n π-electrons) or nonaromatic (does not meet the criteria for aromaticity).

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주요 개념

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Aromaticity

Aromatic compounds are cyclic, planar molecules with a ring of resonance that follow Hückel's rule, which states they must have 4n + 2 π electrons (where n is a non-negative integer). This delocalization of electrons contributes to their stability and unique chemical properties. Common examples include benzene and its derivatives.
추천 영상:
가이드 코스
08:19
Intro to Aromaticity

Antiaromaticity

Antiaromatic compounds are also cyclic and planar but contain 4n π electrons, leading to destabilization due to the presence of electron-electron repulsion in the ring. This instability often results in higher reactivity compared to nonaromatic compounds. An example of an antiaromatic compound is cyclobutadiene.
추천 영상:
가이드 코스
02:58
Determine the aromaticity

Nonaromaticity

Nonaromatic compounds do not meet the criteria for aromaticity or antiaromaticity. They may be acyclic, lack planarity, or have an insufficient number of π electrons. These compounds do not exhibit the special stability associated with aromatic systems and typically behave like aliphatic compounds. An example is cyclohexane.
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(d)

(e)

(f)

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(a)

(b)

(c)

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a. Which of its rings are aromatic?

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(b) Which nitrogen atoms are basic?

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