compounds with oxygen atoms
DESCRIPTION
Compounds with Oxygen Atoms. Alcohols -OH hydroxyl CH 3 - OH CH 3 CH 2 - OH Phenols Ethers -O- CH 3 -O- CH 3. Learning Check. Classify each as an alcohol (1), phenol (2), or an ether (3): - PowerPoint PPT PresentationTRANSCRIPT
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