Alcohols, Phenols and Ethers.ppt

8/14/2019 Alcohols, Phenols and Ethers.ppt

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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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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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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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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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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-1-ol, 1-propanol,methanol

methyl alcohol


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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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OH OH

OH

OHOH

Cl Cl

Cl

phenol 3-methylphenol4-ethylphenol

2,4,6-trichlorophenol benzyl alcohol

alcohol


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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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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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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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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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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
http://en.wikipedia.org/wiki/File:Alcohol_to_aldehyde_to_acid.png


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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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CH3

CH

2

OH CH3 O

H

CH3 O

OH

ethanol acetaldehyde acetic acid

oxydation oxydation
http://en.wikipedia.org/wiki/File:Alcohol_to_aldehyde_to_acid.pnghttp://en.wikipedia.org/wiki/File:Alcohol_to_acid.png


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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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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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http://upload.wikimedia.org/wikipedia/commons/3/38/Possible_long-term_effects_of_ethanol.png


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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.
http://en.wikipedia.org/wiki/File:Methanol_flat_structure.pnghttp://en.wikipedia.org/wiki/File:Methanol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Methanol-2D.png


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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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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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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
http://en.wikipedia.org/wiki/File:Phenol-3D-vdW.pnghttp://en.wikipedia.org/wiki/File:Phenol-3D-balls.pnghttp://en.wikipedia.org/wiki/File:Phenol-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:Phenol2.svg


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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.
http://en.wikipedia.org/wiki/File:Phenol-2D-skeletal.png


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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.
http://en.wikipedia.org/wiki/File:2,6-bis%281,1-dimethylethyl%29-4-methylphenol.svg


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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).
http://en.wikipedia.org/wiki/File:Hexylresorcinol.svghttp://en.wikipedia.org/wiki/File:Raspberry_ketone.png


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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.
http://en.wikipedia.org/wiki/File:Apigenin.png


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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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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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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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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)
http://en.wikipedia.org/wiki/File:Thiol_group.svg


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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)
http://en.wikipedia.org/wiki/File:Cysteine.svghttp://en.wikipedia.org/wiki/File:Cysteine.svghttp://en.wikipedia.org/wiki/File:Cystine-skeletal.pnghttp://en.wikipedia.org/wiki/File:Cystine-skeletal.pnghttp://en.wikipedia.org/wiki/File:Cystine-skeletal.pnghttp://en.wikipedia.org/wiki/File:Cystine-skeletal.pnghttp://en.wikipedia.org/wiki/File:Cystine-skeletal.pnghttp://en.wikipedia.org/wiki/File:Cysteine.svg


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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.
http://en.wikipedia.org/wiki/File:Diallyl_disulfide.pnghttp://en.wikipedia.org/wiki/File:Diallyl-disulfide-3D-vdW.png


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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.
http://en.wikipedia.org/wiki/File:Coenzym_A.svghttp://en.wikipedia.org/wiki/File:Coenzym_A.svghttp://en.wikipedia.org/wiki/File:Coenzym_A.svg


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Alcohols, Phenols and Ethers.ppt

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