What are alcohols? An alcohol contains a hydroxyl group (—OH) attached to a carbon chain. A phenol contains a hydroxyl group (—OH) attached to a benzene.

What are alcohols?

An alcohol contains a hydroxyl group (—OH) attached to a carbon chain.

A phenol contains a hydroxyl group (—OH) attached to a benzene ring.

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alcohol

water

phenol

How do we name alcohols?

Formula IUPACName

CH4 methane

CH3─OH methanol

CH3─CH3 ethane

CH3─CH2─OH ethanolThe names of

alcohols• in IUPAC replace

the -e with -ol.

More names of alcohols

CH3─CH2─CH2─OH

1-propanol

OH │CH3─CH─CH2─CH3 2-butanol

CH3 OH │ │CH3─CH─CH2─CH2─CH─CH3

5-methyl-2-hexanol6 5 4 3 2 1

• IUPAC names for longer chains number chain from – end nearest -OH

group.

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What are phenols?

OH

OH

CH2CH2CH2CH2CH2CH3

OH OH

OH

Phenol• IUPAC name for benzene with a

hydroxyl group.• is used in antiseptics and disinfectants.

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phenol resorcinol 4-hexylresorcinol

Derivatives of Phenol

Compounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint.

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How to name a phenol!

Br

OH

Cl

OH

63-chlorophenol 4-bromophenol

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4

1 1

To name a phenol• with two substituents, assign C-1 to carbon

attached to –OH.• Number ring to give lowest numbers.

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• determined by number of alkyl groups attached to carbon bonded to hydroxyl.

• primary (1°), secondary (2°), or tertiary(3).

Primary (1º) Secondary (2º) Tertiary (3º)1 group 2 groups 3 groups H CH3 CH3

| | | CH3—C—OH CH3—C—OH CH3—C—OH

| | | H H CH3

Classification of alcohols

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What are ethers?

An ether• contains an ─O─ between two carbon groups.• has a common name that gives alkyl names of

attached groups followed by ether. CH3─O─CH3 CH3─CH2─O─CH3

dimethyl ether ethyl methyl ether

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Ethers as anesthetics

Anesthetics • inhibit pain signals to the brain.• like diethyl ether CH3─CH2─O─CH2─CH3 were

used for over a century, but caused nausea and were flammable.

• developed by the 1960’s were nonflammable. Cl F F Cl F

H │ │ │ │ │ │ H─C─C─O─C─H H─C─C─O─C─H │ │ │ │ │ │ F F F H F

H Ethane(enflurane) Penthrane

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Now let’s look at the Properties of Alcohols and

Ethers, Alcohols• contain polar OH groups. • form hydrogen bonds with other

alcohol molecules.• have higher boiling points than alkanes and ethers of similar mass.

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However ethers…………

Ethers• do not have a

polar group.• have an O atom,

but there is no H attached.

• cannot form hydrogen bonds between ether molecules.

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Solubility of alcohols and ethers in water

Alcohols and ethers • are more soluble in water than alkanes

because the oxygen atom can hydrogen bond with water.

• with 1-4 C atoms are soluble, but not with 5 or more C atoms.

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Reactions of alcohols are…

Alcohols undergo combustion with O2 to produce CO2 and H2O.

2CH3OH + 3O2 2CO2 + 4H2O + Heat

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Alcohols undergo• dehydration when heated with an acid

catalyst.• the loss of —H and —OH from adjacent carbon

atoms. H OH

| | H+, heatH—C—C—H H—C=C—H + H2O

| | | | H H H H alcohol alkene

Dehydration of Alcohols

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Oxidation vs Reduction

In an oxidation, • there is an increase in the number of C-O bonds.• there is a loss of H.

In a reduction,• there is an decrease in the number of C-O bonds.• there is a gain of H.

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When a primary alcohol is oxidized, [O],• one H is removed from the –OH. • another H is removed from the carbon bonded to

the OH.• an aldehyde is produced.

[O] Primary alcohol Aldehyde

OH O | [O] ||

CH3—C—H CH3—C—H + H2O

| H

Ethanol Ethanal (ethyl alcohol) (acetaldehyde)

Oxidation of primary (1) alcohols

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Oxidation of secondary (2) alcohols

When a secondary alcohol is oxidized, [O],• one H is removed from the –OH.• another H is removed from the carbon bonded to the OH.• a ketone is produced.

secondary alcohol [O] ketone

OH O │ ║

CH3─C─CH3 [O] CH3─C─CH3 + H2O │

H 2-propanol 2-propanone

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Oxidation of tertiary ( 3)alcoholsTertiary 3alcohols do not readily oxidize.

[O]Tertiary alcohol no reaction OH │ [O] CH3─C─CH3 no product │ CH3 no H on the C-OH to oxidize

2-methyl-2-propanol

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Oxidation of Ethanol in the Body

In the body,• enzymes in the liver oxidize ethanol.• aldehyde product impairs coordination.• blood alcohol over 0.4% can be fatal.

O O ║ ║CH3CH2OH CH3CH CH3COH 2CO2 +

H2Oethyl alcohol acetaldehyde acetic acid

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Ethanol• acts as a depressant.• kills or disables more

people than any other drug.• is metabolized at a rate of

12-15 mg/dL per hour by a social drinker.• is metabolized at a rate of 30 mg/dL per hour by an alcoholic.

Ethanol CH3CH2OH% Ethanol Product50% Whiskey, rum,

brandy40% Flavoring

extracts15-25% Listerine,

Nyquil, Scope12% Wine, Dristan,

Cepacol3-9% Beer, Lavoris

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What do Aldehydes and Ketones have in common?

A carbonyl group• in an aldehyde is

attached to at least one H atom.

• in a ketone is attached to two carbon groups.

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More examples!

H

O

C

H

O

CCH=CH

Benzaldehyde (almonds)

Benzaldehyde (almonds)

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How to name ketones

In naming ketones• as IUPAC, -e in alkane name replaced with –

one.• With a common name, alkyl groups attached to

carbonyl group are named alphabetically followed

by ketone. O O

║ ║CH3 ─C─CH3 CH3─C─CH2─CH3 propanone 2-butanone

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Are they soluble? aldehydes and ketones• electronegative O atom of carbonyl group

• aldehydes and ketones • hydrogen bonds with water

• not between each other, thus• higher boiling points • alkanes and ethers of similar mass.

• lower boiling points• alcohols of similar mass.

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Reactions of aldehydes

Aldehydes oxidize readily to carboxylic acids. Ketones do not oxidize further

O O || || CH3—C—H CH3—C—OH

oxidation

O ||CH3—C— CH3------- NO REACTION

oxidation