LecturePLUS Timberlake1 1.5 Alcohols and Ethers. Alcohols.

LecturePLUS Timberlake 1

1.5Alcohols and

Ethers

Alcohols

Alcohols• Contain one or more hydroxyl groups, —OH

• Named from parent hydrocarbon; suffix changed to -ol and number designates carbon to which hydroxyl is attached.

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Compounds with Oxygen Atoms

Alcohols -OH hydroxyl CH3-OH

CH3CH2-OH

Phenols

Ethers -O- CH3-O-CH3

OHOH

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Learning Check Al1

Classify each as an alcohol (1), phenol (2), or an ether (3):

A. _____ CH3CH2-O-CH3 C. _____ CH3CH2OH

B. _____

OH

CH3

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Solution Al 1

Classify each as an alcohol (1), phenol (2), or an ether (3):

A. __3__ CH3CH2-O-CH3 C. __1__ CH3CH2OH

B. _ 2__

OH

CH3

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Naming AlcoholsA carbon compound that contain -OH

(hydroxyl) group In IUPAC name, the -e in alkane name is

replaced with -ol.

CH4 methane

CH3OH methanol (methyl alcohol)

CH3CH3 ethane

CH3CH2OH ethanol (ethyl alcohol)

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More Names of Alcohols IUPAC names for longer chains number the

chain from the end nearest the -OH group.

CH3CH2CH2OH 1-propanol

OH CH3CHCH3 2-propanol

CH3 OH CH3CHCH2CH2CHCH3 5-methyl-2-hexanol

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Some Typical Alcohols OH “rubbing alcohol” CH3CHCH3

2-propanol (isopropyl alcohol)

antifreeze HO-CH2-CH2-OH1,2-ethanediol (ethylene glycol)

OH

glycerol HO-CH2-CH-CH2OH

Anti-

freez

e

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Learning Check Al 2

Name the following alcohols:A. OH

CH3CHCHCH2CH3

CH3

OHB.

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Solution Al 2

Name the following alcohols:A. OH 3-methyl-2-pentanol

CH3CHCHCH2CH3

CH3

OHB. cyclobutanol

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Phenols

IUPAC name for benzene with a hydroxyl group

Many are used as antiseptics and disinfectants

OH

Phenol

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Phenols in Medicine

OH

OH

OH OH

OHCH2CH2CH2CH2CH2CH3

Resorcinol 4-Hexylresorcinal(antiseptic) (antiseptic)

Phenol

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Ethers

• Contain an -O- between two carbon groups• Formed by a condensation reaction of 2

alcohols to remove a molecule of water• Methanol reacts with methanol to formCH3-O-CH3 methoxy methane

Methanol reacts with ethanol to form

CH3-O-CH2CH3 methoxy ethane

Ethers

• Tend to be quite unreactive.• Therefore, they are good polar

solvents.

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Ethers as Anesthetics

Anesthetics inhibit pain signals to the brainCH3CH2-O-CH2CH3 used for over a century

(Morton, 1846)Causes nausea and is highly flammable1960s developed nonflammable anesthetics

Cl F F Cl F H

H-C-C-O-C-H H-C-C-O-C-H

F F F H F H

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MTBE2-Methoxy-2-methyl propane (methy tert-butyl ether)

CH3

CH3-O-C-CH3

CH3

Second in production or organic chemicals Additive to improve gasoline performanceUse in question with discovery of contaminated

water supplies