ALCOHOLS, PHENOL and ETHERS

 

Reference: McMurry Ch 8 George et al Ch 2.2 2.4

 

  

Nomenclature

 

Alcohols: Rules for naming alcohols follow the guidelines already given for alkanes, in summary

Examples:

Ethers: Two ways of naming ethers

Examples: 

 

Structure and properties

 

Name

Structure

Molecular Mass

bp ( C)

Water Solubility

Ethanol

CH3CH2OH

46

78

3

Dimethyl ether

CH3OCH3

46

-24

7

Propane

CH3CH2CH3

44

-42

7

1-butanol

CH3CH2CH2CH2OH

74

117

(3 )

Diethyl ether

CH3CH2OCH2CH3

74

35

7

Phenol

C6H5OH

94

182

(3 )

 

 

 

Reactions of Alcohols, Phenol and Ethers

 

1. Acid-base reaction of alcohols and phenol

 

 

Example:

 

Relative acidities

 

 

 

pKa

React with

Na

React with

OH-

React with

HCO3-

Ethanol

CH3CH2OH

16.0

ü

X

X

Phenol

C6H5OH

9.9

ü

ü

X

Acetic Acid

CH3COOH

4.8

ü

ü

ü

 

 

2. Oxidation of alcohols

 

 

 

3. Nucleophilic substitution of alcohols

 

 

Example

4. Elimination of water from alcohols

 

Alcohols can also undergo an elimination reaction to form an alkene. H2O is eliminated from the alcohol so the reaction is also called a dehydration reaction

 Example:

 

5 ETHERS

 

Ethers tend to be unreactive and consequently make good solvents.

 

Some biologically active compounds containing the alcohol functional group:

 

Questions on Alcohols

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