Alcohol, Phenols, and Ethers - Review Flashcards

Vocabulary flashcards covering preparations, reactions, mechanisms, named processes, and diagnostic tests for phenols and ethers based on the lecture transcript.

Dow Process

A commercial process for preparing phenol by heating chlorobenzene with aqueous sodium hydroxide ($\text{NaOH}$) at a high temperature ($300\,^\circ\text{C}$) and high pressure ($200\,\text{atm}$), proceeding via a benzyne intermediate.

Phenoxide Ion

The resonance-stabilized anion ($\text{C}_6\text{H}_5\text{O}^-$) formed when phenol loses a proton ($\text{H}^+$), characterized by five resonating structures that delocalize negative charge onto the benzene ring.

Cumene

The common name for isopropylbenzene ($\text{C}_6\text{H}_5\text{CH(CH}_3)_2$), an aromatic hydrocarbon used as the primary starting material in the industrial synthesis of phenol.

Cumene Process

An industrial method for synthesizing phenol and acetone by oxidizing cumene with air to cumene hydroperoxide, followed by cleavage using dilute acid.

Picric Acid

The common name for $2,4,6\text{-trinitrophenol}$, a yellow-colored acid synthesized by nitrating phenol with concentrated nitric acid.

Kolbe's Reaction

An organic reaction in which sodium phenoxide reacts with carbon dioxide ($\text{CO}_2$) followed by acidification to yield salicylic acid ($2\text{-hydroxybenzoic acid}$).

Reimer-Tiemann Reaction

The conversion of phenol to salicylaldehyde ($2\text{-hydroxybenzaldehyde}$) by reaction with chloroform ($\text{CHCl}_3$) and aqueous alkali ($\text{NaOH}$ or $\text{KOH}$).

Dichlorocarbene

A neutral, electron-deficient reactive intermediate ($\text{:CCl}_2$) generated from chloroform and a strong base, which serves as the electrophile in the Reimer-Tiemann reaction.

Salicylaldehyde

The chemical compound $2\text{-hydroxybenzaldehyde}$, formed as the primary product when phenol undergoes the Reimer-Tiemann reaction using chloroform and aqueous sodium hydroxide.

Aspirin

The common name for acetylsalicylic acid, synthesized by reacting salicylic acid with acetyl chloride or acetic anhydride in the presence of pyridine.

Oil of Wintergreen

The common name for methyl salicylate, an ester prepared by heating salicylic acid with methanol ($\text{CH}_3\text{OH}$) in an acidic medium.

Salol

The common name for phenyl salicylate, produced by the reaction of salicylic acid with phenol in the presence of an acid catalyst.

Para-Benzoquinone

A pink-colored conjugated diketone formed through the oxidation of phenol when exposed to air, sunlight, or strong oxidizing agents such as sodium dichromate ($\text{Na}_2\text{Cr}_2\text{O}_7$) and sulfuric acid.

Ferric Chloride Test

A qualitative test for identifying phenolic groups, where phenol reacts with neutral ferric chloride ($\text{FeCl}_3$) to produce a characteristic violet-colored complex.

Liebermann's Nitroso Test

A test for phenols with an unsubstituted para position, in which reaction with sodium nitrite ($\text{NaNO}_2$) and concentrated sulfuric acid produces a deep blue color that turns red on dilution and deep blue again upon adding sodium hydroxide.

Phthalein Dye Test

A diagnostic reaction where phenol is heated with phthalic anhydride and concentrated sulfuric acid to yield phenolphthalein, which turns pink upon alkalinization with sodium hydroxide.

Fries Rearrangement

An acid-catalyzed rearrangement converting phenyl acetate into a mixture of ortho- and para-hydroxyacetophenone in the presence of anhydrous Lewis acids such as $\text{AlCl}_3$.

Williamson Ether Synthesis

An $\text{S}_\text{N}2$ nucleophilic substitution process for synthesizing symmetrical or unsymmetrical ethers by reacting an alkyl halide with a sodium alkoxide or phenoxide.

Denaturation of Alcohol

The process of rendering ethanol unfit for human consumption by adding poisonous or foul-smelling substances such as copper sulfate or pyridine.

Diazonium Coupling Reaction

A reaction in which benzene diazonium chloride reacts with phenol in a basic medium to produce para-hydroxyazobenzene, an orange-colored azo dye.