酚
苯酚中的羟基使芳香环活化，无需卤素载体催化剂即可与溴水反应。
- 官能团
- Ar-OH
概览
Aromatic compounds with hydroxyl groups bonded directly to the ring.
In a phenol the hydroxyl group is attached directly to an aromatic ring. Phenol is more acidic than an ordinary alcohol because its conjugate base is resonance-stabilised. Benzyl alcohol has a -CH2- spacer and must be treated as an alcohol, not as a phenol.
Identifiers
- 官能团
- Ar-OH
化学标识符
- SMILES
- Oc1ccccc1
性质
- 酸碱性质
- 氢氧化物水溶液可将苯酚转化为苯氧负离子；酸化可使其恢复为中性的苯酚。
- 环的反应活性
- 羟基使苯环更易发生亲电取代；可取代位置影响产物。
Diagnostic tests
溴水检验苯酚
- 试剂
- 溴水
- 条件
- 在室温下向水溶液样品中加入溴水并振摇。
- Positive observation
- 溴的颜色消失，并生成白色的 2,4,6-三溴苯酚沉淀
- Negative observation
- 不生成白色沉淀
- Interpretation
- 褪色并生成白色沉淀，支持存在苯酚或具有类似活化苯环的酚类。
- 适用范围
- 苯酚无需卤素载体催化剂即可与溴水反应。
- 来源说明
- 烯烃可使溴水褪色，沉淀形成是另一项观察。
- 证据
- 教材核心内容
Related compounds
- 双酚 A
所选 PC 合成路线中，两端带酚羟基的结构单元。
- 苯酚
一种芳香羟基化合物，其酸性不同于醇。
- 2-甲基苯酚
2-甲基苯酚是一种有机化合物，分子式为 C7H8O。
- 3-甲基苯酚
3-甲基苯酚是一种有机化合物，分子式为 C7H8O。
- 4-甲基苯酚
4-甲基苯酚是一种有机化合物，分子式为 C7H8O。
- 邻苯二酚
邻苯二酚是一种有机化合物，分子式为 C6H6O2。
- 间苯二酚
间苯二酚是一种有机化合物，分子式为 C6H6O2。
- 对苯二酚
对苯二酚是一种有机化合物，分子式为 C6H6O2。
- 对乙酰氨基酚
对乙酰氨基酚是一种有机化合物，分子式为 C8H9NO2。
- 水杨酸
同一分子中酚羟基和羧基相邻，是阿司匹林化学中的重要化合物。
- 水杨酸甲酯
一种芳香酯，同时保留独立的酚羟基。
- 香兰素
香兰素是一种有机化合物，分子式为 C8H8O3。
- 丁香酚
丁香酚是一种有机化合物，分子式为 C10H12O2。
- 2,4,6-三溴苯酚
两个邻位及对位均被溴取代的苯酚。
- 2-硝基苯酚
硝基与羟基在苯环上相邻的苯酚衍生物。
- 4-硝基苯酚
羟基和硝基位于苯环对位的苯酚衍生物。
Connected reactions
- Bromination: Phenols → Bromophenols
苯酚使溴水褪色，并形成浅色的 2,4,6-三溴苯酚沉淀。
参考文献
- Organic Chemistry: Properties of Alcohols and PhenolsJohn McMurry · OpenStax Organic Chemistry · 2023
Supports functional-group chemistry used to curate the linked examples. Checked 2026-09-16; named examples are applications of textbook scope, without claimed experimental yields.
- Organic Chemistry: Reactions of PhenolsJohn McMurry · OpenStax Organic Chemistry · 2023
Supports the hydroxyl group as a strongly activating, ortho- and para-directing substituent in electrophilic aromatic halogenation of phenols.
- Pearson Edexcel International Advanced Level Chemistry Practical GuidePearson Education Limited · Pearson qualifications · 2018
Official Pearson practical guidance for organic qualitative tests, including bromine water, acidified dichromate, silver nitrate, carbonyl reagents and the iodoform reaction.
- Polycarbonate melt polymerisation from bisphenol A and diphenyl carbonateAsahi Kasei
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Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: 2-Methylphenol (CID 335)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: 3-Methylphenol (CID 342)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: 4-Methylphenol (CID 2879)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Catechol (CID 289)National Center for Biotechnology Information · PubChem
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- PubChem Compound Summary: Resorcinol (CID 5054)National Center for Biotechnology Information · PubChem
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- PubChem Compound Summary: Hydroquinone (CID 785)National Center for Biotechnology Information · PubChem
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- PubChem Compound Summary: Paracetamol (CID 1983)National Center for Biotechnology Information · PubChem
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- PubChem Compound Summary: Salicylic acid (CID 338)National Center for Biotechnology Information · PubChem
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- PubChem Compound Summary: Methyl salicylate (CID 4133)National Center for Biotechnology Information · PubChem
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- PubChem Compound Summary: Vanillin (CID 1183)National Center for Biotechnology Information · PubChem
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Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
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Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.
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Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.
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Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.