Alcohols,phenols and ethers

Created by K

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What is the process of substituting the hydrogen atom of the hydroxyl group in alcohols or phenols called?

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It is called substitution by an alkyl or aryl group.

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Classification of Alcohols, Phenols, and Ethers

What is the process of substituting the hydrogen atom of the hydroxyl group in alcohols or phenols called?

It is called substitution by an alkyl or aryl group.

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Preparation of Ethers from Alcohols and Alkyl Hali...

How can phenols be converted to ethers?

By using phenol as the phenoxide moiety.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the effect of the alkoxy group (-OR) on the aromatic ring?

It is ortho, para directing and activates the aromatic ring towards electrophilic substitution.

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Classification of Alcohols, Phenols, and Ethers

How are monohydric alcohols classified?

According to the hybridisation of the carbon atom to which the hydroxyl group is attached.

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Acidity of Alcohols and Phenols

What indicates the acidic nature of phenols?

Reactions of phenol with metals and sodium hydroxide.

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Classification of Alcohols, Phenols, and Ethers

What characterizes tertiary alcohols?

The hydroxyl group is attached to a tertiary carbon atom.

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Preparation of Ethers from Alcohols and Alkyl Hali...

What type of alkyl halide gives better results in ether preparation?

Primary alkyl halides.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What mechanism is followed when primary or secondary alkyl groups are present?

The S N 2 mechanism.

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Acidity of Alcohols and Phenols

How does the structure of phenol affect its acidity compared to alcohols?

The sp² hybridized carbon in phenol withdraws electrons, increasing the polarity of the O–H bond.

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Preparation of Alcohols from Various Compounds

How are alcohols produced from Grignard reagents?

By the reaction of Grignard reagents with aldehydes and ketones through nucleophilic addition to the carbonyl group, forming an adduct that is hydrolyzed to yield an alcohol.

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Acidity of Alcohols and Phenols

What makes the phenoxide ion more stable than phenol?

Charge delocalization in phenoxide ion favors its ionization, while phenol has charge separation in its resonance structures.

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Preparation of Alcohols from Various Compounds

What type of alcohol is produced when other aldehydes react with Grignard reagents?

Secondary alcohols.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What happens when phenol is heated with zinc dust?

Phenol is converted to benzene.

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Preparation of Phenols from Different Precursors

What is a significant by-product of phenol production from cumene?

Acetone.

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Classification of Alcohols, Phenols, and Ethers

What are the two main components of alcohols and phenols?

An alkyl/aryl group and a hydroxyl group.

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Preparation of Ethers from Alcohols and Alkyl Hali...

What determines whether ethanol is dehydrated to ethene or ethoxyethane?

The reaction conditions, specifically temperature.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What happens when alkyl aryl ethers are cleaved?

They yield phenol and an alkyl halide due to the more stable aryl-oxygen bond.

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Classification of Alcohols, Phenols, and Ethers

How are the electron pairs arranged in ethers?

Approximately in a tetrahedral arrangement.

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Preparation of Ethers from Alcohols and Alkyl Hali...

How are ethers prepared?

By dehydration of alcohols and Williamson synthesis.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What happens when I⁻ ion attacks an ether?

It breaks the O–CH₃ bond to form CH₃I.

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Chemical Reactions of Alcohols, Phenols, and Ether...

How does anisole react during halogenation?

It undergoes bromination in the presence of bromine in ethanoic acid, even without a catalyst.

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Preparation of Phenols from Different Precursors

How is phenol obtained from chlorobenzene?

By fusing chlorobenzene with NaOH at 623K and 320 atmospheric pressure, followed by acidification of sodium phenoxide.

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Chemical Reactions of Alcohols, Phenols, and Ether...

Why does the reaction follow the S N 1 mechanism with tertiary alkyl groups?

The departure of the leaving group creates a more stable carbocation.

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Acidity of Alcohols and Phenols

What type of acids are alcohols and phenols classified as?

Brönsted acids.

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Acidity of Alcohols and Phenols

Which compound is million times more acidic than ethanol?

Phenol.

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Preparation of Phenols from Different Precursors

How is phenol manufactured from cumene?

Cumene is oxidised in the presence of air to cumene hydroperoxide, which is then converted to phenol and acetone by treating with dilute acid.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the order of dehydration ease for alcohols?

Tertiary > Secondary > Primary.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the order of reactivity of hydrogen halides in the cleavage of ethers?

HI > HBr > HCl.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the role of CrO3 in anhydrous medium?

It is used as an oxidizing agent for the isolation of aldehydes.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What do primary alcohols yield upon oxidation with mild oxidizing agents?

Aldehydes.

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Acidity of Alcohols and Phenols

How do the acidity levels of alcohols compare to water?

Alcohols are weaker acids than water.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What role does anhydrous aluminium chloride play in the Friedel-Crafts reaction?

It acts as a Lewis acid catalyst.

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Classification of Alcohols, Phenols, and Ethers

What type of carbon atom is the hydroxyl group attached to in primary alcohols?

To a primary carbon atom.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the effect of –OH and –CH3 groups on the position of incoming groups in electrophilic substitution?

They determine the position of the incoming group.

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Acidity of Alcohols and Phenols

What is formed when phenols react with aqueous sodium hydroxide?

Sodium phenoxides.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is formed by the protonation of anisole?

Methylphenyl oxonium ion.

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Acidity of Alcohols and Phenols

What is the reason for the acidic character of alcohols?

The polar nature of the O–H bond.

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Preparation of Alcohols from Various Compounds

What are two methods to prepare alcohols from alkenes?

Hydration in the presence of an acid and hydroboration-oxidation reaction.

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Preparation of Phenols from Different Precursors

How can phenols be prepared from haloarenes?

By substitution of the halogen atom with an –OH group.

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Commercial Importance of Alcohols

What is the primary method for worldwide production of phenol?

From cumene.

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Physical Properties of Alcohols, Phenols, and Ethe...

What primarily determines the properties of alcohols and phenols?

The hydroxyl group.

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Chemical Reactions of Alcohols, Phenols, and Ether...

Which reagent is better for oxidizing primary alcohols to aldehydes in good yield?

Pyridinium chlorochromate (PCC).

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is formed in the final step of ethanol dehydration?

Ethene by elimination of a proton.

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Preparation of Ethers from Alcohols and Alkyl Hali...

What is the main product when ethanol is dehydrated at 413 K?

Ethoxyethane.

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Acidity of Alcohols and Phenols

What does the reaction of water with an alkoxide demonstrate?

Water is a better proton donor (stronger acid) than alcohol.

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Preparation of Ethers from Alcohols and Alkyl Hali...

What happens when secondary and tertiary alkyl halides are used in ether preparation?

Elimination competes over substitution.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is formed when phenol is treated with bromine water?

2,4,6-tribromophenol as a white precipitate.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the major product of the reaction between sodium ethoxide and (CH₃)₃C–Br?

2-methylprop-1-ene.

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Classification of Alcohols, Phenols, and Ethers

What are allylic alcohols?

Alcohols where the hydroxyl group is attached to an sp3 hybridised carbon adjacent to a carbon-carbon double bond.

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Classification of Alcohols, Phenols, and Ethers

What are benzylic alcohols?

Alcohols where the hydroxyl group is attached to an sp3 hybridised carbon next to an aromatic ring.

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Classification of Alcohols, Phenols, and Ethers

How are alcohols and phenols classified?

On the basis of the number of hydroxyl groups and the hybridization of the carbon atom to which the –OH group is attached.

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Preparation of Alcohols from Various Compounds

What is the product of the hydroboration-oxidation of alkenes?

Trialkyl boranes, which are then oxidized to alcohols.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the common name for 2,4,6-trinitrophenol?

Picric acid.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the first step in the dehydration mechanism of ethanol?

Formation of protonated alcohol.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What products are formed from the cleavage of dialkyl ethers?

Two alkyl halide molecules are formed.

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Physical Properties of Alcohols, Phenols, and Ethe...

What is the boiling point of methanol?

337 K.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the outcome of the Reimer-Tiemann reaction of phenol?

It yields salicylaldehyde.

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Acidity of Alcohols and Phenols

Why are cresols less acidic than phenol?

Due to the presence of electron-releasing alkyl groups.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What type of bond cleavage occurs in alcohols during certain reactions?

Cleavage of the carbon-oxygen (C–O) bond.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the first step in the reaction of an ether with concentrated HI?

Protonation of the ether molecule.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What role does iodide play in the reaction mechanism?

Iodide is a good nucleophile that attacks the least substituted carbon of the oxonium ion.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What type of halide is formed when one of the alkyl groups is tertiary?

A tertiary halide.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the main product formed when phenoxide ion reacts with carbon dioxide?

Ortho hydroxybenzoic acid.

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Chemical Reactions of Alcohols, Phenols, and Ether...

How does the reactivity of phenoxide ion compare to phenol in electrophilic aromatic substitution?

Phenoxide ion is more reactive than phenol.

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Chemical Reactions of Alcohols, Phenols, and Ether...

Why is the O–CH3 bond weaker than the O–C6H5 bond in anisole?

Because the carbon of the phenyl group is sp2 hybridized, giving it partial double bond character.

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Classification of Alcohols, Phenols, and Ethers

Why is the bond angle in alcohols less than the tetrahedral angle?

Due to the repulsion between the unshared electron pairs of oxygen.

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Acidity of Alcohols and Phenols

What is the effect of electron-withdrawing groups on the acidity of phenols?

They enhance the acidic strength of phenol, especially when present at ortho and para positions.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What happens to phenols in the presence of air?

They are slowly oxidized to dark colored mixtures containing quinones.

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Preparation of Alcohols from Various Compounds

How is methanol primarily produced today?

By catalytic hydrogenation of carbon monoxide at high pressure and temperature.

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Acidity of Alcohols and Phenols

Why is 2,4,6-trinitrophenol considered a strong acid?

Due to the presence of three electron-withdrawing –NO2 groups that facilitate the release of hydrogen ions.

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Physical Properties of Alcohols, Phenols, and Ethe...

Which alcohols are miscible with water in all proportions?

Several lower molecular mass alcohols.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the outcome of the Kolbe’s reaction?

It involves the electrolysis of sodium or potassium salts of carboxylic acids to produce alkenes.

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Preparation of Alcohols from Various Compounds

How are carboxylic acids reduced to alcohols?

By using lithium aluminium hydride (LiAlH4) or by converting them to esters followed by catalytic hydrogenation.

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Preparation of Ethers from Alcohols and Alkyl Hali...

What is the Williamson synthesis reaction for 2-ethoxy-3-methylpentane starting from ethanol and 3-methylpentan-2-ol?

The reaction involves the nucleophilic substitution of the ethoxide ion from ethanol with the alkyl halide derived from 3-methylpentan-2-ol.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the role of Lewis acid in the halogenation of benzene?

It polarizes the halogen molecule.

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Preparation of Ethers from Alcohols and Alkyl Hali...

What is the major product when using a tertiary alkyl halide in ether preparation?

An alkene, specifically 2-methylpropene.

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Acidity of Alcohols and Phenols

What do alcohols and phenols react with to yield alkoxides and hydrogen?

Active metals such as sodium, potassium, and aluminium.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What type of reactions occur on the aromatic ring of phenols?

Electrophilic substitution reactions.

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Chemical Reactions of Alcohols, Phenols, and Ether...

How does the –OH group affect the benzene ring in phenols?

It activates the ring towards electrophilic substitution and directs incoming groups to ortho and para positions.

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Acidity of Alcohols and Phenols

Arrange the following compounds in increasing order of their acid strength: Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophenol, phenol, 4-methylphenol.

Propan-1-ol, 4-methylphenol, phenol, 3-nitrophenol, 3,5-dinitrophenol, 2,4,6-trinitrophenol.

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Acidity of Alcohols and Phenols

What is the trend in acid strength of alcohols based on substituents?

The acid strength decreases with the presence of electron-releasing groups like –CH3 and –C2H5.

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Preparation of Phenols from Different Precursors

How is phenol commercially produced today?

Synthetically.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the carbon–oxygen bond length in phenol?

136 pm.

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Acidity of Alcohols and Phenols

What is the relationship between pKa value and acid strength?

The greater the pKa value, the weaker the acid.

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Preparation of Ethers from Alcohols and Alkyl Hali...

At what temperature does ethanol dehydrate to ethene?

443 K.

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Physical Properties of Alcohols, Phenols, and Ethe...

What effect does branching in the carbon chain have on the boiling points of alcohols?

Boiling points decrease with an increase in branching due to decreased van der Waals forces.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What happens to the O–H bond when alcohols react as nucleophiles?

The bond between O–H is broken.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the role of the –OH group in alcohols and phenols?

It is involved in intermolecular hydrogen bonding.

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Physical Properties of Alcohols, Phenols, and Ethe...

Give an example of two compounds with comparable molecular masses but different boiling points.

Ethanol and propane.

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Chemical Reactions of Alcohols, Phenols, and Ether...

Why do phenols not react further to give halides?

Because the sp² hybridized carbon of phenol cannot undergo nucleophilic substitution needed for conversion to the halide.

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Preparation of Ethers from Alcohols and Alkyl Hali...

What is the appropriate set of reactants for the preparation of 1-methoxy-4-nitrobenzene?

Anisole can be used in a Friedel-Crafts reaction with an alkyl halide and acyl halide in the presence of anhydrous aluminium chloride.

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Acidity of Alcohols and Phenols

What makes alkoxide ions stronger bases than hydroxide ions?

Alkoxide ions are better proton acceptors than hydroxide ions.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the yield of the para isomer obtained from the halogenation of anisole?

90%.

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Acidity of Alcohols and Phenols

What is the effect of charge distribution in phenol's resonance structures?

It causes the oxygen of the –OH group to be positive, enhancing acidity.

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Preparation of Phenols from Different Precursors

What is the process to convert benzenesulphonic acid to phenol?

Benzene is sulphonated with oleum to form benzene sulphonic acid, which is then converted to sodium phenoxide by heating with molten sodium hydroxide, followed by acidification.

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Acidity of Alcohols and Phenols

Why are phenols stronger acids than alcohols?

Phenols have higher ionization due to the electronegativity of the sp² hybridized carbon.

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Preparation of Phenols from Different Precursors

How are diazonium salts formed?

By treating an aromatic primary amine with nitrous acid (NaNO2 + HCl) at 273-278 K.

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Acidity of Alcohols and Phenols

How does the stability of alkoxide ions compare to phenoxide ions?

In alkoxide ions, the negative charge is localized on oxygen, while in phenoxide ions, it is delocalized.

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Preparation of Phenols from Different Precursors

What happens to diazonium salts to produce phenols?

Diazonium salts are hydrolysed to phenols by warming with water or treating with dilute acids.

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Classification of Alcohols, Phenols, and Ethers

What is the bond angle in alcohols compared to the tetrahedral angle?

Slightly less than the tetrahedral angle (109°).

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Preparation of Alcohols from Various Compounds

What type of alcohol is produced when ketones react with Grignard reagents?

Tertiary alcohols.

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Chemical Reactions of Alcohols, Phenols, and Ether...

How can ortho and para isomers of nitrophenol be separated?

By steam distillation.

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Preparation of Phenols from Different Precursors

What is phenol also known as?

Carbolic acid.

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Classification of Alcohols, Phenols, and Ethers

In phenols, to which type of carbon is the –OH group attached?

To sp² hybridised carbon of an aromatic ring.

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Chemical Reactions of Alcohols, Phenols, and Ether...

How does borane add to alkenes during hydroboration?

The boron atom attaches to the sp2 carbon with more hydrogen atoms.

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Physical Properties of Alcohols, Phenols, and Ethe...

What is the reason for the solubility of alcohols and phenols in water?

Their ability to form hydrogen bonds with water molecules.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What products are formed when phenol is treated with bromine in low polarity solvents at low temperature?

Monobromophenols.

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Chemical Reactions of Alcohols, Phenols, and Ether...

Why do reactions with HBr or HI occur?

Because these reagents are sufficiently acidic.

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Acidity of Alcohols and Phenols

Why do alcohols act as Bronsted bases?

Due to the presence of unshared electron pairs on oxygen.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the outcome of the nitration of anisole?

It yields a mixture of ortho and para nitroanisole.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What happens when HI is in excess and the reaction is at high temperature?

Ethanol reacts with another molecule of HI to form ethyl iodide.

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Classification of Alcohols, Phenols, and Ethers

What distinguishes secondary alcohols from primary alcohols?

The hydroxyl group is attached to a secondary carbon atom.

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Physical Properties of Alcohols, Phenols, and Ethe...

What is the nature of the C-O bonds in ethers?

The C-O bonds in ethers are polar, resulting in a net dipole moment.

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Physical Properties of Alcohols, Phenols, and Ethe...

How do the boiling points of ethers compare to those of alcohols?

Ethers have lower boiling points than alcohols due to the absence of hydrogen bonding in ethers.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the Reimer-Tiemann reaction?

It is the reaction where phenol is treated with chloroform in the presence of sodium hydroxide, introducing a –CHO group at the ortho position of the benzene ring.

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Physical Properties of Alcohols, Phenols, and Ethe...

What is the boiling point of butan-1-ol compared to ethoxyethane?

Butan-1-ol has a boiling point of 390 K, while ethoxyethane has a boiling point of 307.6 K.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What product is formed from the hydrolysis of the intermediate benzal chloride in the Reimer-Tiemann reaction?

Salicylaldehyde.

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Classification of Alcohols, Phenols, and Ethers

How are alcohols and phenols classified based on the number of hydroxyl groups?

As mono-, di-, tri-, or polyhydric compounds.

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Physical Properties of Alcohols, Phenols, and Ethe...

Why are ethers miscible with water like alcohols?

Ethers can form hydrogen bonds with water molecules, similar to alcohols.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What conditions are required for the cleavage of C-O bonds in ethers?

Cleavage occurs under drastic conditions with excess hydrogen halides.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is produced when phenol is oxidized with chromic acid?

Benzoquinone, a conjugated diketone.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What strong oxidizing agent is used to convert alcohols directly into carboxylic acids?

Acidified potassium permanganate.

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Commercial Importance of Alcohols

What is methanol also known as?

Wood spirit.

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Acidity of Alcohols and Phenols

How do electron-releasing groups affect the acidity of phenols?

They generally decrease the acid strength by not favoring the formation of phenoxide ion.

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Preparation of Phenols from Different Precursors

From what are phenols prepared in the laboratory?

From benzene derivatives.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is the major product of acid-catalyzed dehydration of butan-1-ol?

The major product is typically butene.

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Preparation of Alcohols from Various Compounds

What catalysts are commonly used for the reduction of aldehydes and ketones?

Finely divided metals such as platinum, palladium, or nickel.

p.11
Physical Properties of Alcohols, Phenols, and Ethe...

How do boiling points of alcohols and phenols change with the number of carbon atoms?

They increase with an increase in the number of carbon atoms.

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Preparation of Phenols from Different Precursors

What is the first step in the modern preparation of picric acid from phenol?

Treating phenol with concentrated sulfuric acid to convert it to phenol-2,4-disulphonic acid.

p.18
Chemical Reactions of Alcohols, Phenols, and Ether...

What happens to secondary alcohols during oxidation?

They are oxidized to ketones by chromic anhydride (CrO3).

p.17
Chemical Reactions of Alcohols, Phenols, and Ether...

What is the process of oxidation of alcohols characterized by?

Formation of a carbon-oxygen double bond with cleavage of O-H and C-H bonds.

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Chemical Reactions of Alcohols, Phenols, and Ether...

What is acetylation?

The introduction of an acetyl (CH3CO) group in alcohols or phenols.

p.4
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

How are the positions of –OH groups indicated in alcohol nomenclature?

By using the numbers of carbon atoms to which they are attached.

p.23
Preparation of Ethers from Alcohols and Alkyl Hali...

What type of reaction occurs when forming ethers from alcohols?

A nucleophilic bimolecular reaction (S N 2).

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Physical Properties of Alcohols, Phenols, and Ethe...

What is the boiling point of ethanol?

351 K.

p.20
Chemical Reactions of Alcohols, Phenols, and Ether...

What happens to the bromine molecule when phenol is treated with it?

The bromine molecule is polarized even in the absence of Lewis acid due to the activating effect of the –OH group.

p.24
Chemical Reactions of Alcohols, Phenols, and Ether...

Why do alkoxides lead to elimination reactions?

Because they are strong nucleophiles and strong bases.

p.9
Preparation of Alcohols from Various Compounds

What type of alcohol is produced when methanal reacts with Grignard reagents?

A primary alcohol.

p.1
Classification of Alcohols, Phenols, and Ethers

What are the three main classes of compounds discussed in this unit?

Alcohols, phenols, and ethers.

p.1
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the IUPAC system used for?

To name alcohols, phenols, and ethers.

p.1
Preparation of Alcohols from Various Compounds

How are alcohols formed from hydrocarbons?

By replacing a hydrogen atom with a hydroxyl (-OH) group.

p.3
Classification of Alcohols, Phenols, and Ethers

How are ethers classified?

As simple (symmetrical) or mixed (unsymmetrical) based on the similarity of alkyl or aryl groups attached to the oxygen atom.

p.4
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the IUPAC name for methyl alcohol?

Methanol.

p.5
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

How are common names of ethers derived?

From the names of alkyl/aryl groups in alphabetical order, followed by 'ether'.

p.5
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the common name for 1-Methoxypropane?

Methyl n-propyl ether.

p.19
Chemical Reactions of Alcohols, Phenols, and Ether...

What is produced when phenol reacts with dilute nitric acid at low temperature?

A mixture of ortho and para nitrophenols.

p.13
Acidity of Alcohols and Phenols

How do electron-releasing groups affect the acidity of alcohols?

They increase electron density on oxygen, decreasing the polarity of the O-H bond and thus decreasing acid strength.

p.12
Physical Properties of Alcohols, Phenols, and Ethe...

What primarily causes the high boiling points of alcohols?

The presence of intermolecular hydrogen bonding.

p.23
Preparation of Ethers from Alcohols and Alkyl Hali...

What is the process by which alcohols undergo dehydration?

In the presence of protic acids like H2SO4 or H3PO4.

p.19
Chemical Reactions of Alcohols, Phenols, and Ether...

What is the effect of concentrated nitric acid on phenol?

It converts phenol to 2,4,6-trinitrophenol (picric acid).

p.12
Physical Properties of Alcohols, Phenols, and Ethe...

How does the size of alkyl/aryl groups affect the solubility of alcohols?

Solubility decreases with an increase in the size of alkyl/aryl (hydrophobic) groups.

p.21
Acidity of Alcohols and Phenols

Why are ortho and para nitrophenols more acidic than phenol?

Due to the resonance structures of the corresponding phenoxide ions that stabilize the negative charge.

p.8
Preparation of Alcohols from Various Compounds

What is the result of reducing aldehydes and ketones?

Aldehydes yield primary alcohols, while ketones yield secondary alcohols.

p.22
Preparation of Alcohols from Various Compounds

What is ethanol obtained from commercially?

Fermentation of sugars.

p.17
Chemical Reactions of Alcohols, Phenols, and Ether...

What happens to a primary alcohol during oxidation?

It is oxidized to an aldehyde, which is then oxidized to a carboxylic acid.

p.8
Commercial Importance of Alcohols

Who first reported the hydroboration-oxidation reaction?

H.C. Brown in 1959.

p.29
Physical Properties of Alcohols, Phenols, and Ethe...

What is the boiling point comparison of ethers to alkanes?

The boiling points of ethers resemble those of alkanes.

p.29
Chemical Reactions of Alcohols, Phenols, and Ether...

What effect does the –OH group have on the aromatic ring in phenols?

It activates the ring towards electrophilic substitution and directs incoming groups to ortho and para positions.

p.5
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the IUPAC name for o-Cresol?

2-Methylphenol.

p.3
Classification of Alcohols, Phenols, and Ethers

What is an example of a symmetrical ether?

Diethyl ether (C2H5OC2H5).

p.5
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the common name for 1-Phenoxyheptane?

Heptyl phenyl ether.

p.29
Acidity of Alcohols and Phenols

What is the effect of electron withdrawing groups on the acidity of phenols?

They increase the acidic strength of phenols.

p.17
Chemical Reactions of Alcohols, Phenols, and Ether...

Which step in the dehydration mechanism is the rate determining step?

Formation of carbocation.

p.4
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

How is the name of an alcohol derived according to the IUPAC system?

By substituting 'e' of the alkane with the suffix 'ol'.

p.22
Chemical Reactions of Alcohols, Phenols, and Ether...

What are the dangers of methanol ingestion?

Can cause blindness and death.

p.18
Chemical Reactions of Alcohols, Phenols, and Ether...

Do tertiary alcohols undergo oxidation reactions?

No, tertiary alcohols do not undergo oxidation reactions.

p.4
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the naming convention for polyhydric alcohols?

Retain the 'e' of alkane and add 'ol', indicating the number of –OH groups with prefixes like di, tri, etc.

p.4
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

How is ethylene glycol named in IUPAC nomenclature?

As ethane-1,2-diol.

p.5
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the common name for 2-Methylphenol?

o-Cresol.

p.16
Chemical Reactions of Alcohols, Phenols, and Ether...

What happens to tertiary alcohols in the Lucas test?

They produce turbidity immediately as they form halides easily.

p.1
Preparation of Ethers from Alcohols and Alkyl Hali...

What are ethers formed from?

By substituting a hydrogen atom in a hydrocarbon with an alkoxy or aryloxy group.

p.3
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the common name for CH3OH?

Methyl alcohol.

p.3
Classification of Alcohols, Phenols, and Ethers

What distinguishes mixed ethers from symmetrical ethers?

Mixed ethers have different alkyl or aryl groups, while symmetrical ethers have the same groups.

p.8
Chemical Reactions of Alcohols, Phenols, and Ether...

What is the outcome of the hydroboration-oxidation reaction in relation to Markovnikov's rule?

The alcohol formed appears as if water was added in a way opposite to Markovnikov's rule.

p.7
Chemical Reactions of Alcohols, Phenols, and Ether...

What causes the carbon–oxygen bond in phenol to be shorter than in methanol?

Partial double bond character due to conjugation with the aromatic ring and sp² hybridised state of carbon.

p.16
Chemical Reactions of Alcohols, Phenols, and Ether...

What is the role of concentrated sulfuric acid in the reaction with carboxylic acid and acid anhydride?

It facilitates the reaction and helps remove water as soon as it is formed.

p.12
Chemical Reactions of Alcohols, Phenols, and Ether...

Arrange the following in order of increasing boiling points: Methanol, ethanol, propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol.

Methanol, ethanol, propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol.

p.22
Preparation of Alcohols from Various Compounds

What enzymes are involved in the fermentation of sugars to produce ethanol?

Invertase and zymase.

p.17
Chemical Reactions of Alcohols, Phenols, and Ether...

Why are tertiary carbocations easier to form?

They are more stable than secondary and primary carbocations.

p.16
Chemical Reactions of Alcohols, Phenols, and Ether...

How do alcohols react with hydrogen halides?

They form alkyl halides and water.

p.3
Classification of Alcohols, Phenols, and Ethers

What types of alcohols can allylic and benzylic alcohols be classified as?

Primary, secondary, or tertiary.

p.3
Classification of Alcohols, Phenols, and Ethers

What is a vinylic alcohol?

An alcohol containing an —OH group bonded to a carbon-carbon double bond.

p.23
Preparation of Ethers from Alcohols and Alkyl Hali...

What type of attack does the alkoxide ion perform in Williamson synthesis?

S N 2 attack on primary alkyl halide.

p.6
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the IUPAC name for C2H5OC2H5?

Diethyl ether.

p.15
Chemical Reactions of Alcohols, Phenols, and Ether...

What do alcohols and phenols react with to form esters?

Carboxylic acids, acid chlorides, and acid anhydrides.

p.4
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What determines the numbering of the longest carbon chain in alcohols?

It is numbered starting at the end nearest to the hydroxyl group.

p.7
Chemical Reactions of Alcohols, Phenols, and Ether...

What is the bond length of C–O in ethers compared to alcohols?

Almost the same (141 pm).

p.16
Commercial Importance of Alcohols

What product is formed from the acetylation of salicylic acid?

Aspirin.

p.8
Commercial Importance of Alcohols

What prestigious award did H.C. Brown receive for his work on boron-containing organic compounds?

The 1979 Nobel Prize in Chemistry.

p.4
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What prefix is used for cyclic alcohols?

Cyclo.

p.1
Classification of Alcohols, Phenols, and Ethers

What is the general formula for an alcohol?

One or more hydroxyl (OH) groups directly attached to carbon atoms.

p.11
Physical Properties of Alcohols, Phenols, and Ethe...

How does the boiling point of alcohols and phenols compare to hydrocarbons and ethers of comparable molecular masses?

They have higher boiling points.

p.18
Chemical Reactions of Alcohols, Phenols, and Ether...

What occurs when vapors of primary or secondary alcohols are passed over heated copper at 573 K?

Dehydrogenation takes place, forming an aldehyde or a ketone.

p.12
Chemical Reactions of Alcohols, Phenols, and Ether...

What occurs to the C–O bond when alcohols react as electrophiles?

The bond between C–O is broken.

p.17
Chemical Reactions of Alcohols, Phenols, and Ether...

What is another term for oxidation reactions of alcohols?

Dehydrogenation reactions.

p.16
Chemical Reactions of Alcohols, Phenols, and Ether...

What distinguishes the reactivity of different classes of alcohols with HCl?

The Lucas test, which shows varying turbidity based on the class of alcohol.

p.5
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What are the dihydroxy derivatives of benzene known as?

1,2-, 1,3-, and 1,4-benzenediol.

p.4
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the IUPAC name for isopropyl alcohol?

Propan-2-ol.

p.6
Chemical Reactions of Alcohols, Phenols, and Ether...

What type of bond connects the oxygen of the –OH group to carbon in alcohols?

A sigma (σ) bond.

p.7
Preparation of Alcohols from Various Compounds

What is one method for preparing alcohols from alkenes?

By acid catalysed hydration.

p.18
Chemical Reactions of Alcohols, Phenols, and Ether...

What is the consequence of methanol oxidation in the body?

It produces methanal and then methanoic acid, which may cause blindness and death.

p.18
Chemical Reactions of Alcohols, Phenols, and Ether...

How is a methanol poisoned patient treated?

By giving intravenous infusions of diluted ethanol.

p.18
Chemical Reactions of Alcohols, Phenols, and Ether...

What enzyme is involved in the oxidation of aldehyde to acid?

The enzyme responsible for this reaction is swamped by ethanol, allowing time for kidneys to excrete methanol.

p.6
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What prefix is added when both alkyl groups are the same in ethers?

The prefix 'di' is added before the alkyl group.

p.23
Commercial Importance of Alcohols

Why was diethyl ether replaced as an inhalation anesthetic?

Due to its slow effect and unpleasant recovery period.

p.5
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the IUPAC name for Ethyl phenyl ether?

Ethoxybenzene.

p.29
Chemical Reactions of Alcohols, Phenols, and Ether...

What happens to the C–O bond in ethers when treated with hydrogen halides?

It can be cleaved.

p.7
Preparation of Alcohols from Various Compounds

What rule does the addition reaction of unsymmetrical alkenes follow?

Markovnikov’s rule.

p.7
Preparation of Alcohols from Various Compounds

What is the first step in the mechanism of alcohol formation from alkenes?

Protonation of alkene to form carbocation by electrophilic attack of H₃O⁺.

p.22
Commercial Importance of Alcohols

What is denaturation of alcohol?

Mixing copper sulfate and pyridine to make it unfit for drinking.

p.22
Chemical Reactions of Alcohols, Phenols, and Ether...

How does ethanol affect the central nervous system?

In moderate amounts, it affects judgment and lowers inhibitions; higher concentrations can cause nausea and loss of consciousness.

p.16
Chemical Reactions of Alcohols, Phenols, and Ether...

What is the result of dehydrating alcohols?

They form alkenes.

p.16
Commercial Importance of Alcohols

What properties does aspirin possess?

Analgesic, anti-inflammatory, and antipyretic properties.

p.1
Commercial Importance of Alcohols

What role do alcohols, phenols, and ethers play in industry?

They are basic compounds for the formation of detergents, antiseptics, and fragrances.

p.1
Commercial Importance of Alcohols

What is the impact of hydroxyl-containing compounds on daily life?

They are essential for products like paper, furniture polish, and textiles.

p.23
Preparation of Ethers from Alcohols and Alkyl Hali...

What is a key requirement for the preparation of ethers from alcohols?

The alkyl group should be primary and unhindered.

p.23
Preparation of Ethers from Alcohols and Alkyl Hali...

Why is bimolecular dehydration not suitable for preparing ethyl methyl ether?

Because elimination competes over substitution in secondary and tertiary alcohols.

p.23
Preparation of Ethers from Alcohols and Alkyl Hali...

What is Williamson synthesis used for?

The preparation of symmetrical and unsymmetrical ethers.

p.1
Commercial Importance of Alcohols

What is the significance of hydroxyl groups in everyday life?

They are found in many compounds like ethanol, sugar, and cotton, which are essential for daily activities.

p.4
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What terms are used to describe the positions of substituents in phenols?

Ortho, meta, and para.

p.6
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

How are ethers classified in the IUPAC system?

As hydrocarbon derivatives where a hydrogen atom is replaced by an –OR or –OAr group.

p.3
Classification of Alcohols, Phenols, and Ethers

What are the classifications of phenols based on the number of hydroxyl groups?

Mono, di, and trihydric phenols.

p.6
Physical Properties of Alcohols, Phenols, and Ethe...

What are the structural aspects depicted in Fig. 7.1?

Structures of methanol, phenol, and methoxymethane.

p.12
Chemical Reactions of Alcohols, Phenols, and Ether...

How can the reactions of alcohols and phenols be categorized?

Based on the cleavage of O–H and C–O bonds.

p.7
Preparation of Alcohols from Various Compounds

What happens in the second step of the alcohol formation mechanism?

Nucleophilic attack of water on the carbocation.

p.7
Preparation of Alcohols from Various Compounds

What is the final step in the mechanism of alcohol formation?

Deprotonation to form an alcohol.

p.5
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the common name for 1,2-benzenediol?

Catechol.

p.3
Classification of Alcohols, Phenols, and Ethers

What is the structure of a vinylic alcohol?

CH2=CH–OH.

p.22
Chemical Reactions of Alcohols, Phenols, and Ether...

What happens if the alcohol percentage exceeds 14% during fermentation?

The action of zymase is inhibited.

p.4
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the common name for the simplest hydroxy derivative of benzene?

Phenol.

p.1
Commercial Importance of Alcohols

What is an example of an alcohol mentioned in the text?

Ethanol.

p.6
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What does the larger (R) group represent in ether nomenclature?

The parent hydrocarbon.

p.6
Chemical Reactions of Alcohols, Phenols, and Ether...

What hybridized orbitals are involved in the bond between carbon and oxygen in alcohols?

An sp³ hybridized orbital of carbon and an sp³ hybridized orbital of oxygen.

p.11
Physical Properties of Alcohols, Phenols, and Ethe...

What is the boiling point of methoxymethane in relation to ethanol and propane?

It is intermediate between the two boiling points.

p.23
Preparation of Ethers from Alcohols and Alkyl Hali...

What reactants are involved in Williamson synthesis?

An alkyl halide and sodium alkoxide.

p.1
Classification of Alcohols, Phenols, and Ethers

What distinguishes phenols from alcohols?

Phenols have -OH groups attached to carbon atoms of an aromatic system, while alcohols have them in an aliphatic system.

p.16
Chemical Reactions of Alcohols, Phenols, and Ether...

What conditions are required for the dehydration of ethanol?

Heating with concentrated H2SO4 at 443 K.

p.5
IUPAC Nomenclature of Alcohols, Phenols, and Ether...

What is the IUPAC name for Dimethyl ether?

Methoxymethane.

Study Smarter, Not Harder
Study Smarter, Not Harder