Bwcopy Alcohols And Ethers

Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones Alcohols, Phenols, and Thiols Ethers Reactions of Alcohols

LecturePLUS Timberlake

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Compounds with Oxygen Atoms Alcohols -OH hydroxyl

CH3-OH CH3CH2-OH

OH

OH

Phenols

Ethers

-OLecturePLUS Timberlake

CH3-O-CH3

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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

OH

B. _____ CH3 LecturePLUS Timberlake

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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

OH

B. _ 2__ CH3 LecturePLUS Timberlake

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Naming Alcohols  A 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 LecturePLUS Timberlake CH3CH2OH ethanol

(ethyl alcohol5)

Ethanol CH3CH2OH Acts as a depressant Kills or disables more people than any other drug 12-15 mg/dL ethanol metabolized by a social drinkers in one hour 30 mg/dL ethanol metabolized by an alcoholic in one hour. LecturePLUS Timberlake

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Alcohol in Some Products % Ethanol

Product

50% 40% 15-25% 12% 3-9%

Whiskey, rum, brandy Flavoring extracts Listerine, Nyquil, Scope Wine, Dristan, Cepacol Beer, Lavoris

LecturePLUS Timberlake

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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 CH3

2-propanol OH

CH3CHCH2CH2CHCH 5-methyl-2-hexanol 8 3 LecturePLUS Timberlake

Some Typical Alcohols CH3CHCH3

2-propanol (isopropyl alcohol) antifreeze

An ti-f ree

“rubbing alcohol”

ze

OH

HO-CH2-CH2-OH 1,2-ethanediol (ethylene glycol) OH

glycerol HO-CH2LecturePLUS -CH-CH Timberlake 2OH

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Learning Check Al 2 Name the following alcohols: A. OH CH3CHCHCH2CH3 CH3 OH B. LecturePLUS Timberlake

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Solution Al 2 Name the following alcohols: A. OH 3-methyl-2-pentanol CH3CHCHCH2CH3 CH3 OH B.

cyclobutanol LecturePLUS Timberlake

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Phenols IUPAC name for benzene with a hydroxyl group OH Many are used as antiseptics and disinfectants

Phenol LecturePLUS Timberlake

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Phenols in Medicine OH

OH

OH

OH

OH CH2CH2CH2CH2CH2CH3

Phenol

Resorcinol (antiseptic) LecturePLUS Timberlake

4-Hexylresorcinal (antiseptic) 13

Thiols Contain the functional group -SH Named by adding thiol to the name of the longest carbon chain Number the -SH group in longer chains CH3-SH

methanethiol

CH3-CH2SH

ethanethiol

SH CH3-CH-CHLecturePLUS 2-propanethiol 3 Timberlake

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Thiols Many thiols have disagreeable odors Used to detect gas leak Found in onions, oysters, garlic and oysters Onions CH3CH2CH2-SH Garlic CH2= CHCH2-SH Skunk spray CH3

1-propanethiol 2-propene-1-thiol

trans-2-butene-1-thiol

CH = CH CH2SH

LecturePLUS Timberlake

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Ethers • Contain an -O- between two carbon groups • Simple ethers named from -yl names of the attached groups and adding ether. CH3-O-CH3

dimethyl ether

CH3-O-CH2CH3 ethyl methyl ether

LecturePLUS Timberlake

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Ethers as Anesthetics Anesthetics inhibit pain signals to the brain CH3CH2-O-CH2CH3 used for over a century (Morton, 1846) Causes nausea and is highly flammable 1960s developed nonflammable anesthetics Cl F F Cl F H H-C-C-O-C-H F F

H-C-C-O-C-H

F

Ethane(enflurane)

HF LecturePLUS Timberlake

H

Penthrane

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MTBE Methyl tert-butyl ether CH3 CH3-O-C-CH3 CH3 Second in production or organic chemicals Additive to improve gasoline performance Use in question with discovery of contaminated LecturePLUS Timberlake 18 water supplies

Reactions of Alcohols Combustion CH3OH + 2O2 Dehydration H OH H-C-C-H H H alcohol

CO2 + 2H2O + Heat

H+, heat H-C=C-H + H2O H H alkene LecturePLUS Timberlake

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