Phenols, Alcohols, and Ethers Lecture Notes

A collection of practice flashcards covering the properties, reactions, and structures of alcohols, phenols, and ethers as described in the lecture notes.

Why cannot tertiary alcohols be oxidized?

Tertiary alcohols cannot be oxidized due to the unavailability of hydrogen on the hydroxyl-bearing carbon.

What is the product when ethyl alcohol is heated with concentrated sulphuric acid at $170^{\circ}C$?

Ethene ($H_2C=CH_2$) and water ($H_2O$).

What is the order of ease for acid catalyzed dehydration of alcohols?

$$3^{\circ}\text{-alcohol} > 2^{\circ}\text{-alcohol} > 1^{\circ}\text{-alcohol}$$

What is the result of the hydration of an alkene when boiled with water and concentrated sulphuric acid at $100^{\circ}C$?

The corresponding alcohol (e.g., ethyl alcohol from ethene).

What is the hybridization of the carbon and oxygen atoms in an alcohol molecule?

Both the carbon atom bonded to the hydroxyl group and the oxygen atom of the $-OH$ group are $sp^3$-hybridized.

What is the $C-O-H$ bond angle in a methanol molecule?

$$108.9^{\circ}$$

What are the names of the monohydric, dihydric, and trihydric alcohols shown in the notes?

Ethanol (monohydric), Ethylene glycol (dihydric), and Glycerol (trihydric).

What is the physical state of alcohols higher than butanol?

Alcohols higher than butanol are waxy solids.

Which alcohols are noted as being good car fuels with high octane ratings?

Methanol and ethanol.

What substance is commonly used in automotive antifreeze?

Ethyelene glycol.

What is formed when alkaline $KMnO_4$ is added to an alkyne?

A tetrol is formed.

What are the alternative names for phenols?

Carbolic acid, monohydroxybenzene, or benzenol.

What occurs during Dow's Process for producing phenol?

Chlorobenzene is fused with aqueous sodium hydroxide ($NaOH$) at $350^{\circ}C$ and $150$ atmospheric pressures to give sodium phenoxide, which is then acidified with dilute hydrochloric acid to yield phenol.

What are the products of phenol nitration with dilute nitric acid at $25^{\circ}C$?

A mixture of o-nitrophenol ($55\%$) and p-nitrophenol ($45\%$).

What is the $C-O-H$ bond angle in phenol?

$$109^{\circ}$$

What color is pure phenol, and why might it appear red?

Pure phenol is white, but it may look red due to some oxidized impurities.

What is the approximate $pKa$ value of phenols?

$$10$$

What is the $pKa$ value of carboxylic acids?

$$5$$

What oxidizing agent and catalyst are used to convert phenol into benzenequinone?

Potassium dichromate serves as the oxidizing agent and sulphuric acid acts as the catalyst.

What is a common medical use for benzoquinone?

It is used as an antibiotic.

Why do phenols have a higher boiling point than small carbon chain alcohols?

Phenols have stronger hydrogen bonding and a greater surface area available compared to small chain alcohols.

What is the common name for $2, 4, 6\text{-trinitrophenol}$?

Picric acid.

How should picric acid be stored to reduce the risk of explosion when it is in dry form?

It is stored in bottles under a layer of water.

What is the major product formed when phenol is treated with sulphuric acid at $15^{\circ}-20^{\circ}C$?

Ortho phenol sulphonic acid ($2\text{-hydroxyl benzene sulphonic acid}$).

What is the major product formed when phenol is treated with sulphuric acid at $100^{\circ}C$?

Para phenol sulphonic acid ($4\text{-hydroxyl benzene sulphonic acid}$).

How docohols and phenols differ regarding solubility in water?

Alcohols are readily soluble in water, while phenols have lower solubility.

What happens when alcohol reacts with sodium metal?

It forms sodium alkoxide and liberates hydrogen gas ($H_2$), which is indicated by brisk effervescence.

Why is the bond angle in ethers ($110.5^{\circ}$) larger than in water ($104.5^{\circ}$)?

The $CH_3$ groups are large and repel each other significantly, increasing the bond angle.

At what temperature does the dehydration of excess alcohol form an ether?

$$140^{\circ}C$$

What do ethers form when they react with strong acids like concentrated $H_2SO_4$ or $HCl$?

Oxonium salts.