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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 26i,j
16장, 문제 26i,j

Draw the structure of each compound.
(i) tropylium chloride
(j) sodium cyclopentadienide

검증된 단계별 안내
1
Understand the chemical nature of each compound: (i) Tropylium chloride is a salt composed of the tropylium cation (C7H7+) and a chloride anion (Cl-). The tropylium cation is aromatic and has a planar, cyclic structure with 7 carbon atoms and a positive charge. (j) Sodium cyclopentadienide is a salt composed of the cyclopentadienide anion (C5H5-) and a sodium cation (Na+). The cyclopentadienide anion is aromatic and has a planar, cyclic structure with 5 carbon atoms and a negative charge.
For (i) Tropylium chloride: Draw a heptagonal (7-sided) ring to represent the tropylium cation. Place alternating double and single bonds around the ring to indicate aromaticity. Add a positive charge (+) inside or near the ring to represent the cation. Then, add a chloride ion (Cl-) nearby to complete the salt structure.
For (j) Sodium cyclopentadienide: Draw a pentagonal (5-sided) ring to represent the cyclopentadienide anion. Place alternating double and single bonds around the ring to indicate aromaticity. Add a negative charge (-) inside or near the ring to represent the anion. Then, add a sodium ion (Na+) nearby to complete the salt structure.
Ensure that the structures are drawn with proper bond angles and symmetry to reflect the aromatic nature of both the tropylium cation and the cyclopentadienide anion. Aromaticity is confirmed by the Huckel rule (4n+2 π electrons, where n is an integer).
Label each structure clearly as (i) Tropylium chloride and (j) Sodium cyclopentadienide to avoid confusion. Verify that the charges on the cation and anion balance out to form neutral salts in both cases.

비슷한 문제에 대한 검증된 영상 답변:

이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
2m
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주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Tropylium Ion

The tropylium ion is a positively charged aromatic ion derived from toluene. It consists of a seven-membered carbon ring with a positive charge on one of the carbon atoms, making it a stable resonance structure. The aromatic nature of the ring contributes to its stability, allowing it to participate in various chemical reactions.

Cyclopentadiene

Cyclopentadiene is a five-membered cyclic compound with two double bonds. It is known for its ability to form a stable anion when deprotonated, which is crucial for understanding its reactivity. The cyclopentadienyl anion, formed from cyclopentadiene, is a key building block in organic synthesis and coordination chemistry.

Sodium Cyclopentadienide

Sodium cyclopentadienide is the sodium salt of the cyclopentadienyl anion, formed by deprotonating cyclopentadiene with sodium. This compound is a strong nucleophile and is often used in organic synthesis to form new carbon-carbon bonds. Its reactivity is largely due to the stability of the cyclopentadienyl anion, which can participate in various electrophilic substitution reactions.
관련 실천
교과서 질문

Draw the structure of each compound.

(m) p-toluenesulfonic acid

(n) o-xylene

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교과서 질문

Draw the structure of each compound.

(a) o-nitroanisole

(b) 2,4-dimethoxyphenol

(c) p-aminobenzoic acid

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교과서 질문

Four pairs of compounds are shown. In each pair, one of the compounds reacts more quickly, or with a more favorable equilibrium constant, than the less conjugated system. In each case, explain the enhanced reactivity.

(a)

(b)

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교과서 질문

Name the following compounds:

(d)

(e)

(f)

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교과서 질문

The UV spectrum of 1-phenylprop-2-en-1-ol shows an intense absorption at 220 nm and a weaker absorption at 258 nm. When this compound is treated with dilute sulfuric acid, it rearranges to an isomer with an intense absorption at 250 nm and a weaker absorption at 290 nm. Suggest a structure for the isomeric product and propose a mechanism for its formation.

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교과서 질문

Name the following compounds:

(a)

(b)

(c)

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