ALCOHOL PHENOLS ETHERS

OBJECTIVES
Name alcohol compound Understand the importance of alcohol Compare and contrast alcohol, phenol and ether

Importance
Ethanol is a fuel additive, an industrial solvent and a beverage Methanol is a flavoring agent BHT ( butylated hydroxytoluene) an antioxidant food additive Diethyl ether - anesthetic

ALCOHOLS
can be classified as primary, secondary and tertiary Simple alcohols are named using the suffix ol

Alcohols

R
R CH OH R

CH 2
R R C OH

OH

ALCOHOLS
Alcohols are compounds in which an OH group has replaced one of the hydrogen of an alkane. Yet they do not behave like bases such as sodium hydroxide and potassium hydroxide.

NAMING ALCOHOL
Step 1 Select the longest carbon chain containing the hydroxyl group, and replace the e ending of the corresponding alkane with ol

NAMING ALCOHOL
Step 2 Name the carbons of the parent chain beginning at the end nearer the hydroxyl group

NAMING ALCOHOL
Step 3 Number all substituents according to their position on the chain, and write the name listing the substituents in alphabetical order

Common or Radicofunctional Nomenclature The common name of an alcohol is derived by specifying the alkyl group to which the OH group is attached, followed by the separate word alcohol.
HC
Methyl alcohol

OH

H C

CH OH
Isopropyl alcohol

CH

Try this!
OH

HO CH2

CH2 CH2

CH2 CH2

CH3

Common or Radicofunctional Nomenclature Several organic compounds contains two or more OH groups. If compounds contains two hydroxyl group on adjacent carbon atoms - glycols

Common or Radicofunctional Nomenclature

H 2C H CH H CH
1,2-propanediol (propylene glycol)

H 2C H

CH H H

CH2

1,2, -propanetriol (glycerol, glycerin)

CH2CH2

1,2-ethanediol (ethylene glycol)

PHENOL
used to both as the name of specific substance ( hydroxybenzene) and as the family name for all hydroxysubstituted aromatic compounds

Ethers
Simple ethers that contain no other functional groups are named by identifying the two organic groups and adding the word ether

Ethers
If more than one ether linkage is present, or if other functional groups are present, the ether part is named as alkoxy substiuent on the parent compound

Substitutive Nomenclature
The substitutive nomenclature of alcohols and thiols involves an important concept of nomenclature called the principal group. The principal group is the chemical group on which the name is based, and is always cited as a suffix in the name.

Substitutive Nomenclature
For alcohol, the OH is the principal group and the suffix is ol while for simple thiols, the SH is the principal group and its suffix is thiol. Note that only certain groups are cited as principal groups. If a compound does not contain a principal group, it is named as a substituted hydrocarbon.

Substitutive Nomenclature
H3C CH OH
Ethane + ol = ethanol

H3C

CH

SH

Ethane + thiol = ethanethiol

Because the suffix of SH begins with a consonant, the final e of the alkane is retained

IUPAC Rules
The parent hydrocarbon is the longest continuous chain containing the functional group. The parent hydrocarbon is numbered in the direction that gives the functional group suffix the lowest possible number.

IUPAC Rules
H3C
1

CH OH

CH
3

CH3
4

H 3C
5

CH CH
4 3

CH CH
1

OH

H C

CH 3

IUPAC Rules

H3C HC
1 2

CH
3

CH CH CH3
4 5 6

OH

H2C

CH2
7

IUPAC Rules
If there is a functional group suffix and a substituent, the functional group suffix gets the lowest possible number. Notice that a number is not needed to designate the position of a functional group suffix in a cyclic compound because it is assumed to be at the 1-position.

IUPAC Rules
HO CH2 CH2 CH2 CH2 CH2 Br
1 2 3 4 5

H 3C
1

CH CH2
2 3

CH2 Cl
4

H 3C
3 2 1

HO

OH

IUPAC Rules
If the same number for the functional group suffix is obtained in both directions, the chain is numbered in the direction that gives a substituent the lowest possible number.

H 3C
1

CH CH
2 3

CH2 CH3
4 5

Cl H

IUPAC Rules

H 3C
1

CH CH 2 H C
2 3 4

CH 2 CH 2
5 6

CH 3
7

H 3C

OH

IUPAC Rules
If there is more than one substituent, the substituents are cited in alphabetical order. Remember that the name of a substituent is stated before the name of the parent hydrocarbon, and the functional group suffix is stated after the name of the parent hydrocarbon.

IUPAC Rules

H C H 3C CH Br CH CH
4

CH3 CH
3

CH OH

CH3
1

IUPAC Rules
H3C
5 1

4 3

CH2 CH3

1 4

CH3

CH3

General Rules for Substitutive Nomenclature of Organic compound Identify the principal group
When a structure has several candidates for principal group, the group chosen is the one given the highest priority by the IUPAC: Carboxylic acid > anhydride > ester > acid halide > Amide > nitrile > aldehyde > Ketone > alcohol, phenol > thiol > amine

General Rules for Substitutive Nomenclature of Organic compound Identify chain. the principal carbon

The principal chain is the carbon chain on which the name is based. The principal chain is identified by applying the following criteria in order until a decision can be made: greatest number of principal groups greatest number of double and triple bonds greatest length greatest number of other substituents

General Rules for Substitutive Nomenclature of Organic compound Number the principal chain consecutively from one end.
In numbering the principal chain, apply the following criteria in order until there is no ambiguity: lowest numbers for the principal groups lowest numbers for multiple bonds, with double bonds having priority over triple bonds lowest numbers for other substituents lowest number for substituent cited first in the name.

General Rules for Substitutive Nomenclature of Organic compound Begin construction of the name with the name of the hydrocarbon corresponding to the principal chain.
Cite the principal group by its suffix and number; its number is the last one cited in the name.

General Rules for Substitutive Nomenclature of Organic compound Begin construction of the name with the name of the hydrocarbon corresponding to the principal chain.
If there is no principal group, name the compound as a substituted hydrocarbon. Cite the names and numbers of the other substituents in alphabetical order at the beginning of the name.

Nomenclature of Ethers and Sulfides

Ethers are compounds in which oxygen is bonded to two alkyl substituents while sulfides are compounds in which the sulfur is bonded to two alkyl substituents.

Nomenclature of Ethers and Sulfides

If the alkyl substituent are identical, the ether/sulfide is a symmetrical ether/sulfide, otherwise, it is an asymmetrical ether/sulfide.

Nomenclature of Ethers and Sulfides

ROR Symmetrical ether RSR symmetrical sulfide

R O R R S R Asymmetrical ether Asymmetrical sulfide

Common Nomenclature
The common name of ether is constructed by citing as separate words the two groups attached to the ether oxygen in alphabetical order, followed by the word ether.

Common Nomenclature
CH3CH2 O CH2CH3 Diethyl ether CH3 CH2 O CH3 ethyl methyl ether

Common Nomenclature
CH3 H3C CH O CH3 CH CH2 CH3

CH3 H3C CH CH2 O C CH3 H3C CH3

Common Nomenclature
H3C CH CH2 H3C CH2 O

Common Nomenclature
A sulfide is named in a similar manner, using the word sulfide. ( In older literature, the word thioether was also used

Common Nomenclature
CH3CH2 S CH3 Ethyl methyl sulfide (CH3)2CH S CH(CH3)2 diisopropyl sulfide

Substitutive Nomenclature
In substitutive nomenclature, ethers and sulfides are never cited as principal groups. Alkoxy groups (RO - ) and alkylthio groups (RS -) are always cited as substituents.

Substitutive Nomenclature
CH3OCH3CH2O Methoxy ethoxy CH3C(CH3)HOisopropoxy

CH3CH2C(CH3)HO sec-butoxy

CH3C(CH3)2O tert butoxy

Substitutive Nomenclature
H 3C H 3C CH O CH CH CH3 CH CH CH3

S CH3 H3C
1

-(methylthio) hexane

CH

CH
3

CH
4

CH CH3

The parentheses in the name of the sulfide are used to indicate that thio is associated with methyl rather than with hexane.

Heterocyclic Nomenclature
A number of important ethers and sulfides contain an oxygen or sulfur atom within a ring. Cyclic compounds with rings that contain more than one type of atom are called heterocyclic compounds.

Heterocyclic Nomenclature
O H2C CH2 H2C CH2

ethylene oxide

ethylene

O Ph HC CH2 Ph CH CH2
styrene

styrene oxide

Heterocyclic Nomenclature
The IUPAC for tetrahydrofuran, oxolane, is not commonly used except in indexes such as Chemical Abstract
O O S

fura

ra

r fura r THF

Heterocyclic Nomenclature
Oxirane is the parent compound of a special class of heterocyclic ethers, called epoxides, that contain three membered-rings. A few epoxides are named traditionally as oxides of the corresponding alkenes:

Heterocyclic Nomenclature

O O

O
1 ,4 - d ox ne or s m y d ox ne

ox r ne or e h y ene ox de

Heterocyclic Nomenclature
However, most epoxides are named substitutively as derivatives of oxirane. The atoms of the epoxide ring are numbered consecutively with the oxygen receiving the number 1 regardless of the substituent present.

Heterocyclic Nomenclature

O
1

H2C
2

CH
3 i

CH2 CH3
e

2-ethyl

Properties Of Alcohols, Phenols And Ethers: Hydrogen Bonding

Alcohols, phenols, and ethers can be thought of as organic derivatives of water in which one or both of the hydrogens have been replaced by organic parts: HOH becomes R OH or ROR.

Properties Of Alcohols, Phenols And Ethers: Hydrogen Bonding

Thus all three compounds have nearly the same geometry as water. Alcohols have higher boiling points than alkanes or haloalkenes of similar molecular weight.

Properties Of Alcohols, Phenols And Ethers: Acidity

Alcohols and phenols, like water, are both weakly basic and weakly acidic. As weak acids, alcohols and phenols dissociate to a slight extent in dilute aqueous solution by donating a proton to water, generating H2O and alkoxide ion (RO-) or a phenoxide ion (ArO-).

Alcohols
Alcohols react with alkali metals just as water does to yield metal alkoxides that are themselves strong bases.

Methanol
Or methyl alcohol, CH3OH, is produced commercially from either carbon monoxide or carbon dioxide. It is a colorless liquid, which boils at 650C Smells and tastes like ethyl alcohol

Methanol
Is poisonous- breathing the vapor or drinking the liquid may cause blindness or death. Is used in the manufacture of formaldehyde and other organic products; as solvent for resins, gums and shellac

Ethanol
C2H5OH Called ethyl alcohol, grain alcohol is the most important alcohols. prepared by fermentation of starch, cellulose, and various sugars

Ethanol
Large quantities of ethanol are synthesized from ethylene and acetylene Is a colorless liquid with a characteristic and somewhat pleasant odor It is miscible with water in all proportions

Ethanol
Boiling point of pure alcohol is 78.370C It is the least toxic of all the alcohols and is found in all alcoholic beverages

Ethanol
Used as a solvent in tinctures, essences, and extracts Preparation of iodoform, ether, dyes, perfumes, and collodion Solvent in the lacquer industry and as motor fuel Used as additive in some brands of unleaded gasoline.

APPLICATION
Ethanol is classified for medical purposes as a depressant as a central nervous system (CNS) depressant. Increase excitability and increase in social behavior, but this results from depression of inhibition rather than from stimulation

APPLICATION
At a blood alcohol concentration of 0.1% to 0.3%, motor coordination is affected, accompanied by loss of balance, slurred speech and amnesia.

Application
When blood alcohol concentration rises to 0.3% to 0.4%,nausea and loss of consciousness occur. At concentrations greater than 0.6%, spontaneous respiration and cardiovascular regulation are affected, ultimately leading to death.

Application
The passage of ethanol through the body begins with its absorption in the stomach and small intestines, followed by rapid distribution to all body fluids and organs.

Application
In the pituary gland, ethanol inhibit the production of hormone that regulates urine flow, causing increased urine production and dehydration.

Application
In the stomach ethanol, ethanol stimulates production of acid. Throughout the body, ethanol causes blood vessels to dilate, resulting in flushing of the skin and a sensation of warmth as blood moves into capillaries beneath the surface.

Application
The result is not warming of the body, but an increased loss of heat at the surface.

Phenols
Aromatic counterparts of alcohol. The word phenol is used both as the name of a specific substance (hydroxyl-benzene) and as the family name for all hydroxylsubstituted aromatic compounds. Phenols are named with phenol used as the parent name rather than benzene.

Phenols
Phenols have higher boiling points than aromatic hydrocarbons. Phenol itself, for example, boils at 182oC, whereas toluene boils at 110.6oC. Alcohols and phenols have unusually high boiling points because, like water, they from hydrogen bonds in the liquid state.

Phenols
Phenols are about a million times more acidic than alcohols. In fact, some nitro-substituted phenols approach or surpass the acidity of carboxylic acids. One practical consequence of this acidity is that phenols are soluble in dilute aqueous NaOH, but alcohols are not.

Ethers
Simple ethers that contain no other functional groups are named by identifying the two organic groups and adding the word ether.

Ethers
If more than one ether linkage is present, or if other functional groups are present, the ether part is named as alkoxy substituent on the parent compound.

Ethers
Ethers, because they lack hydorxyl groups, cant form hydrogen bonds and therefore have lower boiling points.