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Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711당신이 사용하는 게 아니라요?교과서 변경
19장, 문제 10a

Draw the product formed when pyridine reacts with ethyl bromide

검증된 단계별 안내
1
Identify the functional groups and reactivity of the reactants: Pyridine is an aromatic heterocyclic compound with a nitrogen atom in the ring, and ethyl bromide is an alkyl halide (R-Br). The nitrogen in pyridine has a lone pair of electrons, making it a nucleophile.
Recognize the type of reaction: This is a nucleophilic substitution reaction (SN2 mechanism) because the nitrogen in pyridine will attack the electrophilic carbon in ethyl bromide, displacing the bromide ion (Br⁻).
Determine the site of attack: The lone pair on the nitrogen atom in pyridine will attack the carbon atom bonded to the bromine in ethyl bromide. This forms a bond between the nitrogen and the ethyl group.
Account for the charge: After the nitrogen in pyridine forms a bond with the ethyl group, it will carry a positive charge because it now has four bonds (quaternary ammonium ion).
Draw the product: The final product is an ethylpyridinium ion, where the ethyl group is attached to the nitrogen atom of pyridine, and the bromide ion (Br⁻) is the counterion.

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주요 개념

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the case of pyridine reacting with ethyl bromide, the nitrogen atom in pyridine acts as a nucleophile, attacking the electrophilic carbon bonded to the bromine, leading to the formation of a new bond and the release of bromide ion.
추천 영상:
01:47
Nucleophiles and Electrophiles can react in Substitution Reactions.

Pyridine Structure and Reactivity

Pyridine is a six-membered aromatic heterocycle containing one nitrogen atom. Its aromatic nature and the presence of a lone pair on the nitrogen make it a weak base and a good nucleophile. Understanding the structure of pyridine is crucial, as it influences its reactivity in nucleophilic substitution reactions, particularly how it interacts with alkyl halides like ethyl bromide.
추천 영상:
가이드 코스
1:33
EAS Reactions of Pyridine Concept 1

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (such as bromine). They are often used in nucleophilic substitution reactions due to the polar nature of the carbon-halogen bond, which makes the carbon susceptible to attack by nucleophiles. In this reaction, ethyl bromide serves as the alkyl halide that reacts with pyridine, facilitating the formation of a new product.
추천 영상:
01:52
How to name alkyl halides