Alcohols, Phenols And Ethers.ppt 6u5m3m

ALCOHOLS, PHENOLS and ETHERS

R-OH Functional group of an alcohol molecule

C2H5OH ethanol ethyl alcohol

propan-2-ol, 2-propanol, iso, isopro, isoprop, C3H7OH rubbing alcohol, or the abbreviation IPA – isopropyl alcohol)

Chemistry 21A

Dr. Dragan Marinkovic


Menthol is a major component of mint.

cholesterol

The best source is probably Mentha arvensis, Corn Mint, whose oil is up to 85% (-)-menthol.

High-density lipoprotein (HDL) Chemistry 21A



Glycerin, glycerine, propane-1,2,3-triol Bombykol The sex pheromone of the silk moth

A fatty alcohol with two double bonds, bombykol (tr-10,cis-12-hexadecadien-1-ol), was also shown to be excreted as a very strong attractive substance by the female of silk-worm (Bombyx mori). The bombyx mori silk moth

Chemistry 21A


ALCOHOLS, PHENOLS and ETHERS water

water

water

H O H

H O H

H O H

phenol

alcohol

R O H

O H

phenol group

OH H3C

C H2

H2 C

OH

propan-1-ol

Chemistry 21A

-OH

ether group

ether

R O R O

diethyl ether (ether)

hydroxyl group

R~ alkyl group

O

diphenyl ether


ALCOHOLS, PHENOLS and ETHERS Nomenclature of Alcohols 1. Alcohols are named by finding the longest continues carbon chain and changing the ending to –ol (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 hydroxyl group. The –ol suffix is last and takes precedence in the numbering. 3. If the hydroxyl group 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, ethyl alcohol, etc.)

H3C

OH

methanol methyl alcohol

H3C

H2 C

OH

ethanol ethyl alcohol Chemistry 21A

H3C

H2 C

OH C H2

OH

propan-1-ol, 1-propanol,

C H3C H CH3

propan-2-ol, 2-propanol,



C4H9OH alcohols H2 C

H3C

C H2

H2 C

CH3

OH

OH

CH3 C H3C H C H2

CH3

C OH H3C H C H2

H3C C OH CH3

1-butanol

2-butanol

2-methyl-1-propanol

2-methyl-2-propanol

n-butyl alcohol

sec-butyl alcohol

isobutyl alcohol

tert-butyl alcohol

OH

HO

HO

H2 C

C H2

OH

H2 H2 C H C OH C HO OH

OH

ethanediol ethylene glycol

OH

HO

trans-3-methylcyclohexanol

H3C

OH

OH

1,2,3-propanetriol glycerin

Chemistry 21A

1-methylcyclopentanol Dr. Dragan Marinkovic


OH

OH

3-methylphenol

phenol OH

HO

4-ethylphenol

OH Cl

Cl

alcohol Cl

2,4,6-trichlorophenol Chemistry 21A

benzyl alcohol Dr. Dragan Marinkovic


H2 C

H3C

C H2

H2 C

CH3

OH

OH

CH3

C OH H3C H C H2

CH3 C H3C H C H2

H3C C OH CH3

1-butanol

2-butanol

2-methyl-1-propanol

2-methyl-2-propanol

n-butyl alcohol

sec-butyl alcohol

isobutyl alcohol

tert-butyl alcohol

primary alcohol

tertiary alcohol

primary alcohol

HO

HO

H2 C

C H2

secondary alcohol

OH

OH

H3C

OH

OH

ethanediol ethylene glycol

trans-3-methylcyclohexanol

Chemistry 21A

1-methylcyclopentanol


ALCOHOLS, PHENOLS and ETHERS Water has an unusually high boiling point because of the hydrogen bonds between the H2O molecules. Alcohols can form similar hydrogen bonds.

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 78.5ºC, whereas propane, with about the same molecular weight, boils at -42.1ºC.

The difference in boiling points between alkanes and alcohols with the same number of carbon atoms decreases when the total number of carbons increases (i.e. with the increase of hydrophobic character of alcohols).

CH3CH2OCH2CH3

CH3CH2CH2CH2OH

BP = 34.5ºC

BP = 117.2ºC

d = 0.7138 g/mL

d = 0.8098 g/mL

insoluble in water

soluble in water Chemistry 21A


ALCOHOLS, PHENOLS and ETHERS Solubilities of Alcohols in Water Solubility in Formula Name Water (g/100 g)

CH3OH CH3CH2OH CH3(CH2)2OH

OH OH

methanol

infinitely soluble

ethanol

infinitely soluble

OH

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

Chemistry 21A

OH

hydrophilic part of the molecule

OH

hydrophobic part of the molecule OH



As the length of the alcohol increases, the effect of hydrogen bonding decreases and hydrophobic forces become dominant.

The difference in boiling points between alkanes and alcohols with thw same number of carbon atoms decreases when the total number of carbons increases (i.e. with the increase of hydrophobic character of alcohols).

Chemistry 21A


ALCOHOLS, PHENOLS and ETHERS dehydration reaction

synthesis of ethers H3C

H2 C

C H2

OH

+

HO

Chemistry 21A

C H2

H2 C

H2SO4 CH3

H3C

H2 C

C H2

O

C H2

H2 C

CH3



Chemistry 21A



H3C

C H2

oxydation

oxydation

H

ethanol

acetaldehyde

Chemistry 21A

H3C

O

H3C

OH

O OH

acetic acid



H3C H CH3 C secondary alcohol

oxydation

CH3

H3C O

OH isopropyl alcohol (2-propanol)

dimethyl ketone (acetone)

R R'

OH R"

tertiary alcohol

no reaction oxydation

CH3 H3C

OH

oxydation

no reaction

CH3

Chemistry 21A



C2H5OH ethanol ethyl alcohol

Made from corn and other crops (fermentation)

yeast

C6H12O6

→

C2H5OH + O2

Pure 100% ethanol has an octane rating of 113. Adding 10% ethanol to gasoline raises the overall octane by 2 to 3 points. Lower BTU value than gasoline

2C2H5OH + 2CO2

→

CH3COOH + H2O

H2C

CH2

ethylene (ethene)

70 atm 300oC

H3C

C H2

OH

For most of human history, acetic acid, in the form of vinegar, has been made by acetic acid bacteria of the genus Acetobacter. Chemistry 21A



Chemistry 21A



heat, pressure, catalyst

CO + 2H2

CH3OH

CH3OH → H2C=O → HCOOH methanol formaldehyde formic acid Aqueous solution of formaldehyde is called formalin used for storing specimens and cadavers.

Methanol is produced naturally in the anaerobic metabolism of many varieties of bacteria

common laboratory solvent traditional denaturant for ethanol, thus giving the term methylated spirit

About 40% of methanol is converted to formaldehyde, and from there into products as diverse as plastics, plywood, paints, explosives, and permanent press textiles.

Drag racers and mud racers also use methanol as their primary fuel source. Chemistry 21A



propan-2-ol, 2-propanol, iso, isopro, isoprop, C3H7OH rubbing alcohol, or the abbreviation IPA – isopropyl alcohol)

Ethylene glycol Monoethylene 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 Chemistry 21A



Glycerin, glycerine, propane-1,2,3-triol In foods and beverages, glycerol serves as a humectants, solvent and sweetener, and may help 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.

Chemistry 21A



CH4 < NH3 < HCCH < ROH < H2O < phenols < H2CO3 < RCOOH < HF ONa

OH + NaOH SB

SA water insoluble

+ H2O WB

WA

water soluble

OH + NaHCO3

Chemistry 21A

NR

phenol < H2CO3



Joseph Lister, 1st Baron Lister, (1827 – 1912) was an English surgeon who promoted the idea of sterile surgery 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-Phenylphenol, or ortho-phenylphenol, is an ingredient in Lysol, and is an agricultural fungicide. Chemistry 21A

2-Benzyl-4-chlorophenol is an ingredient in Lysol. Dr. Dragan Marinkovic


4-Chloro-3,5-dimethylphenol, or chloroxylenol, is a nonirritating topical antiseptic used in a number of antibacterial soaps.

2,6-di-tert-butyl-4-methylphenol; 2,6-di-tert-butyl-p-cresol (DBPC); butylated hydroxytoluene; BHT Chemistry 21A

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 fluid



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 either stunning or killing them. They may also be called vermifuges (stunning) or vermicides (killing).

4-hexylbenzene-1,3-diol

Raspberry ketone is a natural phenolic compound 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. Chemistry 21A


ALCOHOLS, PHENOLS and ETHERS 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 foods such as Red Wine, Green Tea, Dark Chocolate, and Super-Berries.

Molecular structure of apigenin, a polyphenol antioxidant Chemistry 21A

A polyphenol antioxidant is a type of antioxidant containing a polyphenolic substructure. In human health these compounds, 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. Dr. Dragan Marinkovic

ALCOHOLS, PHENOLS and ETHERS dimethyl ether, an aerosol spray propellant

ether group ether

R O R O

diethyl ether (ether)

A common low boiling solvent (b.p. 34.6°C), and an early anaesthetic.

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). Polyethylene glycol (PEG) It is the basis of many skin creams, as cetomacrogol, and sexual lubricants, Anisole (methoxybenzene)

O

diphenyl ether Chemistry 21A

An aryl ether and a major constituent of the essential oil of anise seed. Dr. Dragan Marinkovic

ALCOHOLS, PHENOLS and ETHERS 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 ether molecules 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 alcohols solubility in aqueous media similar to analogous alcohols.

CH3CH2OCH2CH3

CH3CH2CH2CH2OH

BP = 34.5ºC

BP = 117.2ºC

d = 0.7138 g/mL

d = 0.8098 g/mL

insoluble in water

soluble in water

Chemistry 21A


ALCOHOLS, PHENOLS and ETHERS 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 same molecular 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 FLAMMABLE and tend, If exposed to air for longer periods of time, to form EXPLOSIVE PEROXIDES.

Chemistry 21A



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 group or a sulfhydryl group. More traditionally, thiols are often referred to as mercaptans.

The preferred method (used by the IUPAC) is to add the suffix -thiol to the name of the alkane. The method is nearly identical to naming an alcohol. Example: CH3SH would be methanethiol. An older method, the word mercaptan replaces alcohol in the name of the equivalent alcohol compound. Example: CH3SH would be methyl mercaptan. (CH3OH would be methyl alcohol)

Chemistry 21A


ALCOHOLS, PHENOLS and ETHERS 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 H3C of mercaptans and sulfides, with t-butyl mercaptan as the main odor constituent.

Cysteine

Chemistry 21A

(oxydation)

CH3 SH CH3

Cystine, showing disulfide bond



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.

Chemistry 21A


ALCOHOLS, PHENOLS and ETHERS 2R-SH + (O) → R-S-S-R + H2O 2CH3SH + (O) → CH3-S-S-CH3 thiol 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. Chemistry 21A



Chemistry 21A



Chemistry 21A


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