S.Y.B.

Sc
Organic Chemistry
Paper I- USCH301
UNIT-III
3.2.1 Alcohol
Subject Teacher: Dr. P. B. Thakur
Topics to be covered

 Introduction to Alcohols
 Nomenclature of Alcohols
 Preparations of Alcohols
 Properties of Alcohols
 Reactions of Alcohols
1. Introduction to Alcohols
Definition:

Examples:
Classification of Alcohol

Examples:
Examples
2. Nomenclature of Alcohols
Common name of an aliphatic monohydric
alcohol is obtained by writing the name of
alkyl group followed by the word alcohol.
Eg; Alkyl Alcohol
Nomenclature of Alcohols by IUPAC
Nomenclature of Alcohols by IUPAC
Examples
Preparations of Alcohols:
 From Alkene
1. Hydration of Alkene
2. Hydration of Alkyl Hydrogen Sulphate
3. Hydroboration Oxidation
 From Alkyl Halides
 From Aldehydes & Ketone
1. Catalytic Hydrogenation
2. Using Lithium Aluminium Hydride
3. Using Sodium borohydride
4. Using Grignard Reagent
1. Preparation of Alcohols from Alkenes

1. Hydration of Alkene
Preparation of Alcohols from Alkenes

2. Hydration of Alkyl Hydrogen Sulphate

Preparation of Alcohols from Alkenes

3. Hydroboration Oxidation
Hydroboration Oxidation
2. Preparation of Alcohols from Alkyl
Halides

1. Hydrolysis of Alkyl Halides

3. Preparation of Alcohols from Aldehydes
& Ketones by Reduction

1. Catalytic Hydrognation
3. Preparation of Alcohols from Aldehydes

& Ketones by Reducation

1. Reduction using Catalytic Hydrognation

2. Reduction using Lithium Aluminium
Hydride
2. Reduction using Sodium borohydride

Aldehydes
2. Reduction using Sodium borohydride

Ketones
Selectivity
Preparation of Alcohols from Aldehydes
& Ketones by Grignard Reagent

General Reaction:
Examples:
Physical Properties of Alcohols

Hydrogen Bonding
Types of Hydrogen Bonding
Intra-Molecular Hydrogen Bond
Effect of Hydrogen bonding on
different properties:

 Effect on Boiling Points

 Effect on Water Solubility

Effect on Boiling Points

Substances having nearly same

molecular weights have the same
boiling points, but due to
presence of Intermolecular
Hydrogen Bonding Alcohols have
Higher Boiling Points compare to
corresponding Alkane and ethers
Example
Effect on Water Solubility

Substances having hydrogen

bonding is usually soluble in
another hydrogen bonded
substance.
Eg. Due to Hydrogen bonding
Alcohol have more solubility in
water as compare to Alkanes
Less solubility of Alkanes in Water
More solubility of Alcohols in Water
Example:
Acidity of Alcohols: Ability to donate H+

 Relative Ease of removal of Proton

 Relative stability of the anion obtained

by the loss of Proton

Alcohols are Extremely weak Acids

 Reactions of Alcohols:
 Hydrogen Halides (HX)
 Thionyl Chloride (SOCl2)
 Phosphorous Halides (PX3 & PX5)

 Dehydration to form Alkene & Ethers

 Esterification with organic acids (R-COOH)
 Esterification with Inorganic acid (H2SO4)

 Oxidation of Alcohols
1. Reaction of Alcohols with Hydrogen
Halides
Alcohols reacts with Hydrogen Halides to
form Alkyl Halides.
Examples: Reactions with HCl
Examples: Reactions with HBr
Examples: Reactions with HI
2. Reactions of Alcohols with Thionyl
Chloride (SOCl2)
 3. Reactions of Alcohols with
Phosphorous Halides (PX3 & PX5)
i) Reactions of Alcohols with PCl3

ii) Reactions of Alcohols with PCl5

Examples: Reactions with PBr3
Examples: Reactions with PBr3
Examples: Reactions with PI3
 4. Dehydration Reactions of Alcohols

i) Dehydration of Alcohols to Form Alkene

Examples:
Selectivity
Selectivity
 4. Dehydration Reactions of Alcohols

ii) Dehydration of Alcohols to Form Ethers

(Etherification)
Examples
Examples
5. Esterification Reactions of Alcohols
with Organic Acids
Examples: with Acids
Examples: with Acid Chlorides
6. Esterification Reactions of Alcohols
with Inorganic Acids (Sulphation)
Application of Sulphation reaction
in synthesis of detergent
7. Oxidation Reactions of Alcohols
7.1 Oxidation of Primary Alcohols
Examples:
7.2 Oxidation of Secondary Alcohols
Examples
7.3 Oxidation of Tertiary Alcohols
Example: