Compounds with Oxygen Atoms

Alcohols -OH hydroxyl CH3-OH

CH3CH2-OH

Phenols

Ethers -O- CH3-O-CH3

OHOH

Learning Check

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

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

B. _____

OH

CH3

Solution

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

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

B. _ 2__OH

CH3

Naming AlcoholsNaming Alcohols

A carbon compound that contain A carbon compound that contain -OH-OH (hydroxyl) group(hydroxyl) group

In IUPAC name, the In IUPAC name, the -e-e in alkane name is in alkane name is replaced with replaced with -ol-ol..

CHCH4 4 methanmethanee

CHCH33OH OH methanmethanolol (methyl alcohol) (methyl alcohol)

CHCH33CHCH33 ethanethanee

CHCH33CHCH22OH OH ethanethanolol (ethyl (ethyl

alcoholalcohol))

Alcohols

How is the -OH group different from the hydroxide ion?

-OH group forms covalent bond with the carbon

Hydroxide ion forms ionic bond with a metal

Ethanol CH3CH2OH

Acts as a depressantKills or disables more people than any

other drug12-15 mg/dL ethanol metabolized by a

social drinkers in one hour 30 mg/dL ethanol metabolized by an

alcoholic in one hour.

Alcohol in Some Products

% Ethanol Product

50% Whiskey, rum, brandy

40% Flavoring extracts

15-25% Listerine, Nyquil, Scope

12% Wine, Dristan, Cepacol

3-9% Beer, Lavoris

More Names of AlcoholsMore Names of Alcohols

IUPAC names for longer chains number the IUPAC names for longer chains number the chain from the end nearest the -OH group.chain from the end nearest the -OH group.

CHCH33CHCH22CHCH22OHOH 1-propanol1-propanol

OHOH CHCH33CHCHCHCH33 2-propanol2-propanol

CHCH3 3 OHOH CHCH33CHCHCHCH22CHCH22CHCHCHCH33 5-methyl-2-5-methyl-2-

hexanolhexanol

Some Typical AlcoholsSome Typical Alcohols

OHOH

““rubbing alcohol”rubbing alcohol” CHCH33CHCHCHCH33

2-propanol (isopropyl alcohol)2-propanol (isopropyl alcohol)

antifreeze antifreeze HO-CHHO-CH22-CH-CH22-OH-OH

1,2-ethanediol (ethylene 1,2-ethanediol (ethylene glycol)glycol)

OHOH

glycerolglycerol HO-CHHO-CH22-CH-CH-CH-CH22OHOH

Ant

i-fre

eze

Classification of AlcoholsClassification of Alcohols

Primary (1º) Secondary (2º ) Tertiary (3º)

H CH3 CH3

CH3-C-OH CH3-C-OH CH3-C-OH

H H CH3

1 C 2 C 3 Cattached attached attachedto C-OH to C-OH to C-OH

Learning CheckLearning Check

Classify the following as 1º, 2º, or 3º alcohols: OH

A. CH3CH2CH2OH B. CH3-CH-CH2CH3

C. D. OH

CH3-C-CH2CH3

CH3

OH

SolutionSolution

Classify the following as 1º, 2º, or 3º alcohols: OH

A. CH3CH2CH2OH 1º B. CH3-CH-CH2CH3 2º

C. 2º D. OH 3º

CH3-C-CH2CH3

CH3

OH

Properties of Alcohols Ethyl alcohol (ethanol) used in the

intoxicating beverages; an important industrial solvent

Many aliphatic alcohols used in laboratories, clinics, and industry

– Isopropyl alcohol (2-propanol) is rubbing alcohol; used as antiseptic, and a base for perfume, creams, lotions, and other cosmetics

Properties of Alcohols

Glycerol (1,2,3-propanetriol) - used as a moistening agent in cosmetics, foods, and drugs; also a component of fats and oils

Learning CheckLearning Check

Name the following alcohols:Name the following alcohols:

A. OH A. OH

CHCH33CHCHCHCHCHCH22CHCH33

CHCH33

OHOH

B. B.

Solution Solution

Name the following alcohols:Name the following alcohols:A. OH A. OH 3-methyl-2-pentanol3-methyl-2-pentanol

CHCH33CHCHCHCHCHCH22CHCH33

CHCH33

OHOHB. B. cyclobutanolcyclobutanol

Properties of Alcohols

Much like water, alcohols are capable of hydrogen bonding between molecules

–this means they will boil at a higher temp. than alkanes and halocarbons with a comparable number of atoms

Properties of Alcohols

Alcohols of up to 4 carbons are soluble in water in all proportions; more than 4 carbons are usually less soluble, because…?

Properties of Alcohols Denatured alcohol- means it has

been made poisonous by the addition of other chemicals, often methyl alcohol (methanol, or wood alcohol). As little as 10 mL of methanol has been known to cause permanent blindness, and 30 ml has resulted in death!!!

Reactions of AlcoholsReactions of Alcohols

CombustionCombustion

CHCH33OH + 2OOH + 2O22 CO CO22 + 2H + 2H22O + O + HeatHeat

DehydrationDehydration

H OHH OH HH++, heat, heat

H-C-C-H H-C-C-H H-C=C-H + H-C=C-H + HH22OO

H H H H H H H H

alcoholalcohol alkene alkene

OxidationOxidation

Is a gain of oxygen (O)

or

A loss of hydrogen (H)

OxidationOxidation of Alcoholsof Alcohols

1°alcohols are oxidized to aldehydes and 2° alcohols are oxidized to ketones

Alcohols 1° 2°

aldehydes ketones

Oxidation of AlcoholsOxidation of Alcohols

[O]

Primary alcohol aldehyde

OH O [O]

CH3-C-H CH3-C-H

H

Ethanol Ethanal

(ethyl alcohol) (acetaldehyde)

Oxidation of AlcoholsOxidation of Alcohols

[O]

Secondary alcohol ketone

OH O [O]

CH3-C-CH3 CH3-C-CH3

2-Propanol 2-propanone (isopropyl alcohol) (dimethyl ketone,

“acetone”)

Oxidation of AlcoholsOxidation of Alcohols

[O]

Tertiary alcohols no reaction

OH [O]

CH3-C-CH3 no product

CH3 no H on the C-OH to oxidize

2-Methyl-2-propanol

Oxidation of Ethanol in the Oxidation of Ethanol in the BodyBody

Enzymes in the liver oxidize ethanolAldehyde product impairs coordinationBlood alcohol over 0.4% can be fatal.

O O

[O] [O]

CH3CH2OH CH3CH CH3COH 2CO2 + H2O

ethyl alcohol acetaldehyde acetic acid

Learning CheckLearning Check

Select the product for the oxidation of CH3CH2CH2OH:

O

1) CH3CH=CH2 2) CO2 + H2O 3) CH3CH2CH

SolutionSolution

Select the product for the oxidation of CH3CH2CH2OH:

O

[O] 3) CH3CH2CH

ReductionReduction

Is a loss of oxygen (O)

or

gain of hydrogen (H)

ReductionReduction

Aldehydes are reduced to 1° alcohols and ketones are reduced to 2° alcohols

Alcohols

1° 2° aldehydes ketones

PhenolsPhenols

IUPAC name for benzene with a IUPAC name for benzene with a hydroxyl hydroxyl groupgroup

Many are used as antiseptics and Many are used as antiseptics and disinfectants disinfectants

OH

Phenol

Phenols in MedicinePhenols in Medicine

OH

OH

OH OH

OH

CH2CH2CH2CH2CH2CH3

Resorcinol 4-Hexylresorcinal(antiseptic) (antiseptic)

Phenol

EthersEthers

Contain an -O- between two carbon Contain an -O- between two carbon groupsgroups

Simple ethers named from -yl names of Simple ethers named from -yl names of the attached groups and adding the attached groups and adding ether.ether.

CHCH33-O--O-CHCH33 dimethyl etherdimethyl ether

CHCH33-O--O-CHCH22CHCH33 ethyl methyl etherethyl methyl ether

Ethers as Anesthetics

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

commonly called just ether (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

Ethane(enflurane) Penthrane

MTBEMTBE

Methyl Methyl terttert-butyl ether-butyl ether

CHCH33

CHCH33-O-C-CH-O-C-CH33

CHCH33

Second in production of organic chemicals Second in production of organic chemicals Additive to improve gasoline performanceAdditive to improve gasoline performance Use in question with discovery of Use in question with discovery of

contaminated water suppliescontaminated water supplies

Learning CheckLearning Check

Write the structure of the following:

A. 3-pentanol

B. Dimethyl ether

C. 3-methylcyclobutanol

Solution Solution

Write the structure of the following:

OH

|

A. 3-pentanol CH3CH2CHCH2CH3

B. Dimethyl ether CH3-O-CH3

C. 3-methylcyclobutanolOH

CH3

ThiolsThiols

Contain the functional group -SH Contain the functional group -SH Named by adding Named by adding thiol thiol to the name of to the name of

the the longest carbon chainlongest carbon chain Number the -SH group in longer chainsNumber the -SH group in longer chains

CHCH33--SH SH methanemethanethiolthiol

CHCH33-CH-CH22SH SH ethaneethanethiolthiol

SHSH

CHCH33-CH-CH-CH-CH33 2-propanethiol2-propanethiol

ThiolsThiols Many thiols have disagreeable odorsMany thiols have disagreeable odors Used to detect gas leakUsed to detect gas leak Found in onions, oysters, garlic and oystersFound in onions, oysters, garlic and oysters

Onions Onions CHCH33CHCH22CHCH22-SH-SH 1-propanethiol 1-propanethiol

Garlic Garlic CHCH22== CHCHCHCH22-SH-SH 2-propene-1-thiol 2-propene-1-thiolSkunk spray Skunk spray

CHCH33 trans-trans-2-butene-1-thiol2-butene-1-thiol

CH = CHCH = CH

CHCH22SHSH