alcohols, phenols and ethers.ppt
TRANSCRIPT
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
Functional group of
an alcoholmoleculeethanol
ethyl alcohol
propan-2-ol, 2-propanol,
iso, isopro, isoprop,
rubbing alcohol, or
the abbreviation IPAisopropyl alcohol)
C3H7OH
C2H5OH-OH
http://en.wikipedia.org/wiki/File:Alcohol_general.svghttp://en.wikipedia.org/wiki/File:Ethanol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Ethanol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Ethanol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Ethanol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Ethanol_flat_structure.pnghttp://en.wikipedia.org/wiki/File:Rubbing_alcohol.JPGhttp://en.wikipedia.org/wiki/File:Isopropanol-3D-vdW.pnghttp://en.wikipedia.org/wiki/File:Isopropanol-skeletal.pnghttp://en.wikipedia.org/wiki/File:Ethanol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Ethanol-3D-vdW.pnghttp://en.wikipedia.org/wiki/File:Ethanol-2D-skeletal.svghttp://en.wikipedia.org/wiki/File:Alcohol_general.svghttp://en.wikipedia.org/wiki/File:Alcohol_general.svg -
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
cholesterol
The best source is probably Mentha arvensis,
Corn Mint, whose oil is up to 85% (-)-menthol.
Menthol is a major component of mint.
High-density lipoprotein (HDL)
http://en.wikipedia.org/wiki/File:Cholesterol.svghttp://en.wikipedia.org/wiki/File:Cholesterol.svghttp://en.wikipedia.org/wiki/File:Menthol.jpghttp://en.wikipedia.org/wiki/File:%28-%29-menthol-3D-vdW.pnghttp://en.wikipedia.org/wiki/File:Menthol-skeletal.pnghttp://en.wikipedia.org/wiki/File:Cholesterol.svg -
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
A fatty alcoholwith two double bonds, bombykol
(tr-10,cis-12-hexadecadien-1-ol), was also shown
to be excreted as a very strong attractive substanceby the female of silk-worm (Bombyx mori).
Glycerin, glycerine, propane-1,2,3-triol
The bombyx mor i
silk moth
Bombykol
The sex pheromone of the silk moth
http://www.chm.bris.ac.uk/motm/bombykol/bombykol.molhttp://www.chm.bris.ac.uk/motm/bombykol/bombyx_mori-moth.jpghttp://www.chm.bris.ac.uk/motm/bombykol/bombykol.molhttp://en.wikipedia.org/wiki/File:Glycerol-3D-vdW.pnghttp://en.wikipedia.org/wiki/File:Glycerol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Glycerin_Skelett.svg -
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
H O H H O HH O H
R O H O H R O R
OCH3 C
H2
C
H2
OH
propan-1-ol
OH
water waterwater
alcohol phenol ether
O
diethyl ether
(ether)
diphenyl ether
-OHhydroxyl group
phenol group
ether group
R~alkyl group
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
Nomenclature of Alcohols
1. Alcohols are named by finding the longest continues carbon chain and changing
the ending tool(e.g., methanol, ethanol, propanol, etc.).2. With unsaturated alcohols, two endings are needed, one for the double or triple
bond and one for the hydroxylgroup. Theolsuffix is lastand takes precedence in
the numbering.
3. If the hydroxylgroup is directly attached to an aromatic ring, the compound is
named as a phenol.
4. If the hydroxyl group occurs in a carboxylic acid, aldehyde, or ketone, it is named
as a substituent (hydroxy) because the former functionalities have higher priority.
5. The common names for the alcohols are the alkane chain named as a substituent
followed by the word alcohol(e.g., methyl alcohol, ethylalcohol, etc.)
CH3
OH
CH3
C
H2
OH CH
3
C
H2
CH
2
OH
CH3
CH CH
3
OH
ethanol
ethyl alcohol
propan-2-ol, 2-propanol,
propan-1-ol, 1-propanol,methanol
methyl alcohol
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
CH3
C
H2
CH
2
C
H2
OH CH3
CH C
H2
CH3
OH
CH3
CH C
H2
OH
CH3
CH3 OH
CH3
CH3
C
1-butanol
n-butyl alcohol
2-butanol
sec-butyl alcohol
2-methyl-1-propanol 2-methyl-2-propanol
C4H9OH alcohols
isobutyl alcohol tert-butyl alcohol
OHC
H2
CH
2
OHOH
C
H2
CH C
H2
OH
OH
OH
OH
OH
OH OH
OHethanediol
ethylene glycol1,2,3-propanetriol
glycerin
trans-3-methylcyclohexanol
1-methylcyclopentanol
OHCH3
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
OH OH
OH
OHOH
Cl Cl
Cl
phenol 3-methylphenol4-ethylphenol
2,4,6-trichlorophenol benzyl alcohol
alcohol
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
CH3
C
H2
CH
2
C
H2
OH CH3
CH C
H2
CH3
OH
CH3
CH CH
2
OH
CH3
CH3 OH
CH3
CH3
C
1-butanol
n-butyl alcohol
2-butanol
sec-butyl alcohol
2-methyl-1-propanol 2-methyl-2-propanol
isobutyl alcohol tert-butyl alcohol
primary alcohol primary alcoholsecondary alcohol tertiary alcohol
OH
trans-3-methylcyclohexanol
OHC
H2
CH
2
OH
OH
OH
ethanediol
ethylene glycol 1-methylcyclopentanol
OHCH3
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
CH3CH2OCH2CH3 CH3CH2CH2CH2OH
BP= 34.5C BP = 117.2C
d= 0.7138 g/mL d= 0.8098 g/mL
insoluble in
watersoluble in water
Water has an unusually high boiling point
because of the hydrogen bonds between the H2O molecules.
Alcoholscan form similar hydrogen bonds.
The difference in boiling
points between alkanes
and alcoholswith the
same number of carbonatoms decreases when
the total number of carbons increases (i.e. with the increase of hydrophobic character of
alcohols).
As a result, alcohols have boiling points that
are much higher than alkanes with similar molecular weights.
The boiling point of ethanol, for example, is 78.5C, whereas propane,
with about the same molecular weight, boils at -42.1C.
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
Solub i l i t ies of A lcoho lsin Water
Formula NameSolubi l i ty in
Water (g/100 g)
CH3OH methanol infinitely soluble
CH3CH2OH ethanol infinitely soluble
CH3(CH2)2OH propanol infinitely soluble
CH3(CH2)3OH butanol 9
CH3(CH2)4OH pentanol 2.7
CH3(CH2)5OH hexanol 0.6
CH3(CH2)6OH heptanol 0.18
CH3(CH2)7OH octanol 0.054
CH3(CH2)9OH decanol insoluble in water
OH
OH
OH
OH
OH
OH
hydrophobicpart of the molecule
hydrophilicpart of the molecule
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
As the length of the alcoholincreases,the effect of hydrogen bonding
decreases and hydrophobic forces
become dominant.
The difference in boiling points between
alkanes and alcoholswith thw same
number of carbon atoms decreases whenthe total number of carbons increases
(i.e. with the increase of hydrophobic
character of alcohols).
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
dehydration reaction
CH3
C
H2
CH
2
OH
CH3
C
H2
CH
2
OH CH3
C
H2
CH
2
OCH
3
C
H2
CH
2
H2SO
4
+
synthesis of ethers
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
http://en.wikipedia.org/wiki/File:Alcohol_to_aldehyde_or_ketone.pnghttp://en.wikipedia.org/wiki/File:Alcohol_to_aldehyde_or_ketone.pnghttp://en.wikipedia.org/wiki/File:Alcohol_to_aldehyde_to_acid.png -
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
CH3
CH
2
OH CH3 O
H
CH3 O
OH
ethanol acetaldehyde acetic acid
oxydation oxydation
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
CH3
CH CH
3
OH
CH3
CH3
O
isopropyl alcohol
(2-propanol)
dimethyl ketone
(acetone)
oxydation
R' OH
R
R"
CH3
OH
CH3
CH3
oxydation
oxydation
no reaction
no reaction
secondaryalcohol
tertiary
alcohol
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
ethanol
ethyl alcohol
C2H5OH
C6H12O6 2C2H5OH + 2CO2yeast
C2H5OH + O2 CH3COOH + H2O
CH3
C
H2
OHCH
2 CH
2
70 atm
300oCethylene
(ethene)
Made from corn and other crops
(fermentation)
Pure 100% ethanol has anoctane rating of 113.
Adding 10% ethanol to
gasoline raises the
overall octane by 2 to 3 points.
Lower BTU value than gasoline
For most of human history, acetic acid,
in the form of vinegar, has been made
by acetic acid bacteria of the genusAcetobacter.
http://en.wikipedia.org/wiki/File:Ethanol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Ethanol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Ethanol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Ethanol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Ethanol_flat_structure.pnghttp://en.wikipedia.org/wiki/File:Ethanol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Ethanol-3D-vdW.pnghttp://en.wikipedia.org/wiki/File:Ethanol-2D-skeletal.svg -
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
CO + 2H2 CH3OH
CH3OH H2C=O HCOOH
heat, pressure, catalyst
methanol formaldehyde formic acid
Aqueous solution of formaldehydeis called formalin used for storing
specimens and cadavers.
Methanol is produced naturally
in the anaerobic metabolism of
many varieties of bacteria
About 40% of methanol is converted to
formaldehyde, and from there intoproducts as diverse as plastics, plywood, paints,
explosives, and permanent press textiles.
common laboratory solvent
traditional denaturant for ethanol,thus giving the term methylated spirit
Drag racers and mud racers
also use methanol as their
primary fuel source.
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
propan-2-ol, 2-propanol,
iso, isopro, isoprop,
rubbing alcohol, or
the abbreviation IPAisopropyl alcohol)
C3H7OH
Ethylene glycolMonoethylene glycol
MEG
1,2-ethanediol
widely used as an
automotive antifreeze
odorless, colorless, syrupy,
sweet tasting, toxic liquid
propylene glycol, 1,2-propanediol,
1,2-Dihydroxypropane, methyl ethyl glycol (MEG),
methylethylene glycol, PG, Sirlene, Dowfrost
moisturizer in medicines,cosmetics, food,
toothpaste, mouth wash, and tobacco products
http://en.wikipedia.org/wiki/File:PropyleneGlycol-spaceFill.pnghttp://en.wikipedia.org/wiki/File:PropyleneGlycol-stickAndBall.pnghttp://en.wikipedia.org/wiki/File:Propylene_glycol_chemical_structure.pnghttp://en.wikipedia.org/wiki/File:Ethylene-glycol-3D-vdW.pnghttp://en.wikipedia.org/wiki/File:Ethylene-glycol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Ethylene_glycol_chemical_structure.pnghttp://en.wikipedia.org/wiki/File:Rubbing_alcohol.JPGhttp://en.wikipedia.org/wiki/File:Isopropanol-3D-vdW.pnghttp://en.wikipedia.org/wiki/File:Isopropanol-skeletal.png -
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
In foods and beverages,
glycerol serves as a humectants,
solvent and sweetener, and mayhelp preserve foods. It is also
used as filler in commercially
prepared low-fat foods (e.g.,
cookies), and as a thickening
agent in liqueurs. Glycerol also
serves as a way, along with water,to preserve certain types of leaves.
Glycerol is also used as a sugar substitute. In this regard, it has approximately 27 calories per
teaspoon and is 60% as sweet as sucrose. Although it has about the same food energy as table
sugar, it does not raise blood sugar levels, nor does it feed the bacteria that form plaques and
cause dental cavities. As a food additive, glycerol is also known as E number E422.
Example of an unsaturated fat triglyceride.
Glycerin, glycerine, propane-1,2,3-triol
http://upload.wikimedia.org/wikipedia/commons/b/be/Fat_triglyceride_shorthand_formula.PNGhttp://upload.wikimedia.org/wikipedia/commons/b/be/Fat_triglyceride_shorthand_formula.PNGhttp://en.wikipedia.org/wiki/File:Glycerol-3D-vdW.pnghttp://en.wikipedia.org/wiki/File:Glycerol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Glycerin_Skelett.svg -
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
OH
+ NaOH
ONa
+ H2O
SA SB WB WA
water insoluble water soluble
OH
+ NaHCO3 NR phenol < H2CO3
CH4< NH3< HCCH < ROH < H2O < phenols < H2CO3< RCOOH < HF
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
Joseph Lister, 1st Baron Lister, (18271912) was
an English surgeon who promoted the idea of sterilesurgery while working at the Glasgow Royal Infirmary.
He successfully introduced carbolic acid (phenol) to
sterilize surgical instruments and to clean
wounds, which led to reduced post-operative
infections and made surgery safer for patients.
2-Benzyl-4-chlorophenol
is an ingredient in Lysol.
2-Phenylphenol, or ortho-phenylphenol,
is an ingredient in Lysol, and is
an agricultural fungicide.
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
Butylated hydroxytoluene (BHT),
also known as butylhydroxytoluene,
is a organic compound that is primarily
used as an antioxidant food additive
(E number E321) as well as in cosmetics,pharmaceuticals, jet fuels, rubber,
petroleum products, and embalming fluid2,6-di-tert-butyl-4-methylphenol;
2,6-di-tert-butyl-p-cresol (DBPC);
butylated hydroxytoluene; BHT
4-Chloro-3,5-dimethylphenol, or chloroxylenol,is a nonirritating topical antiseptic used in
a number of antibacterial soaps.
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
Raspberry ketone is a natural phenoliccompound that is the primary aroma compound
of red raspberries. It is used in perfumery, in
cosmetics, and as a food additive to impart a
fruity odor.
4-hexylbenzene-1,3-diol
4-Hexylresorcinol is a chemical compound with
anaesthetic, antiseptic and antihelmintic properties.It can be used topically on small skin infections,
or as an ingredient in throat lozenges.
Anthelmintics or antihelminthics are drugs that expel
parasitic worms (helminths) from the body, by eitherstunning or killing them. They may also be called
vermifuges (stunning) or vermicides (killing).
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
PHENOLS are next-generation anti-oxidant found throughout nature
in some of the healthiest foods.
PHENOLS are the common health-giving link that ties together foodssuch as Red Wine, Green Tea, Dark Chocolate, and Super-Berries.
Molecular structure of apigenin,
a polyphenol antioxidant
A polyphenol antioxidant is a type of
antioxidant containing a polyphenolic
substructure. In human health thesecompounds, numbering over 4000 distinct
species, are thought to be instrumental in
combating oxidative stress, a process
associated with some neurodegenerative
diseases and some cardiovascular diseases.
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
R O R
O
ether
O
diethyl ether
(ether)
diphenyl ether
ether group dimethyl ether,an aerosol spray propellant
A common low boiling solvent
(b.p. 34.6C), and
an early anaesthetic.
An aryl ether and a major
constituent of the essential
oil of anise seed.
Anisole (methoxybenzene)
Polyethylene glycol (PEG)
Polyethylene glycol has a low toxicity and is used in a variety of
products. It is the basis of a number of laxatives (such as
Movicol and polyethylene glycol 3350, or MiraLax or GlycoLax).
It is the basis of many skin creams, as cetomacrogol, and
sexual lubricants,
http://en.wikipedia.org/wiki/File:Polyethylene_glycol_chemical_structure.pnghttp://en.wikipedia.org/wiki/File:Anisole.svghttp://en.wikipedia.org/wiki/File:Dimethylether_chemical_structure.svg -
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
Physical Properties:
The polar nature of the C-O bond (due to the electronegativity difference
of the atoms ) results in intermolecular dipole-dipole interactions.An ether cannot form hydrogen bonds with other ethermolecules since there
is no H to be donated (no -OH group)
Ethers can be involved in H-bonding with systems able to donate H (e.g. water).
The implications of these effects are:
lower melting and boiling points compared to analogous alcoholssolubility in aqueous media similar to analogous alcohols.
CH3CH2OCH2CH3 CH3CH2CH2CH2OH
BP= 34.5C BP = 117.2C
d= 0.7138 g/mL d= 0.8098 g/mL
insoluble in
watersoluble in water
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
Ethers can act as a hydrogen-bond acceptor, as shown in the figure
below. But, they can't act as hydrogen-bond donors. As a result, ethers
are less likely to be soluble in water than the alcohol with the samemolecular weight.
The absence of an -OH group in an ether also has important
consequences for its chemical properties.
Unlike alcohols, ethers are essentially inert to chemical reactions.
They don't react with most oxidizing or reducing agents, and they are
stable to most acids and bases, except at high temperatures.
They are therefore frequently used as solvents for chemical reactions.However, ethers are generally extremely FLAMMABLEand tend,
If exposed to air for longer periods of time, to form EXPLOSIVE
PEROXIDES.
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
A thiol is a compound that contains the functional group
composed of a sulfur atom and a hydrogen atom (-SH).
Being the sulfur analogue of an alcohol group (-OH), this
functional group is referred to either as a thiol groupor a sulfhydryl group.
More traditionally, thiols are often referred to as mercaptans.
The preferred method (used by the IUPAC) is to add the suffix -thiolto
the name of the alkane. The method is nearly identical to naming an
alcohol. Example: CH3SH would be methanethiol.
An older method, the word mercaptanreplaces alcoholin the name of
the equivalent alcohol compound. Example: CH3SH would be methylmercaptan. (CH3OH would be methyl alcohol)
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
Cysteine Cystine,showingdisulfide
bond
Many thiols are colorless liquids having an odor resembling that of garlic.
The odor of thiols is often strong and repulsive, particularly for those of
low molecular weight
Natural gas distributors began adding various forms of pungent thiols, originally ethanthiol,
to natural gas, which is naturally odorless, after the deadly 1937 New London School
explosion in New London, Texas. Most gas odorants utilized in the world contain mixtures
of mercaptans and sulfides, with t-butyl mercaptan as the main odor constituent.
CH3
SH
CH3
CH3
(oxydation)
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
Diallyl disulfide (4,5-dithia-1,7-octadiene)
is an organosulfur compound, along with
diallyl trisulfide and diallyl tetrasulfide it is one of the
principal components of the distilled oil of garlic.
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
2R-SH + (O) R-S-S-R + H2O
2CH3SH + (O) CH3-S-S-CH3thiol disulfide
2CH3SH + Pb2+ CH3-S-Pb-S-CH3 + 2H
+
Coenzyme A (CoA, CoASH, or HSCoA) is a
coenzyme, notable for its role in the synthesis
and oxidation of fatty acids, and the oxidation
of pyruvate in the citric acid cycle.
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ALCOHOLS PHENOLS and ETHERS
Chemistry 21A Dr. Dragan Marinkovic
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