1. Learning Objectives Preparation of alcohols Intermolecular dehydration
Esterfication
Iodoform reaction
Identification of different alcohols

2. Introduction
Compound having altogether different properties
and applications. Alcohols and phenols are formed
when a hydrogen atom in a hydrocarbon, aliphatic and
aromatic respectively, is replaced by –OH group.

3. Preparation of alcohols
Reduction of carbonyl compounds
Hydration of Alkenes
Grignard reactions

4. Reduction of Carbonyl Compounds
Reduction of aldehydes and ketones
Strong reducing reagent are required.
Reduction of carbohylic acids and their derivatives

5. Reagents used in reduction
Reduce all the compounds except unsaturation
Can not reduce Acids, esters acid anhydride and unsaturation
Can reduce any groups and also unsaturation
Can reduce other groups except acid chloride

6. Hydration of Alkenes Acid catalyzed Hydration
Oxymercuration-Demercuration
Hydroboration-Oxidation

7. Acid-Catalyzed Hydration of Alkenes
Markovnikov addition
Formation of most stable carbocation
Shifts/rearrangements possible

8. Hydration of Alkenes via Oxymercuration/Demercuration
Markovnikov addition
Typically no shifts/rearrangements
Mercurinium ion involvement

9. Hydroboration - Oxidation of Alkenes
Anti-Markovnikov addition
No shifts/rearrangements
Syn addition

10. Grignard Addition Reactions
Addition to Aldehydes/Ketones
Addition to Esters
Addition to Epoxides

11. Grignard Additions to Aldehydes/Ketones
Formation of primary, secondary, and tertiary alcohols

12. Grignard Additions to Esters
Formation of secondary and tertiary alcohols

13. Grignard Addition to Epoxides

14. Typical Alcohol Reactions
Salt formation
Dehydration to alkene
Oxidation to aldehyde, ketone
Substitution to form alkyl halide
Reduction to alkane
Esterification
Williamson synthesis of ether

15. Reaction with Active Metals

16. Dehydration of Alcohols

17. Oxidation of Alcohols Primary RCH OH RCHO RCOOH PCC KMnO or K Cr O ²2 OH
RCHO
RCOOH
PCC
KMnO 4 or K Cr O 7
Secondary R
CHOH
PCC or C
Tertiary 3
COH
no reaction

18. Alcohol Conversion to Alkyl Halides
Reaction with Hydrogen halides
Reaction with Thionyl chloride
Reaction with Phosphorus trihalides or pentahalides

19. Hydrogen halide conversion of alcohols to alkyl halides

20. Alcohols to Alkyl Chlorides via Thionyl Chloride

21. Alcohols to Alkyl Halides via Phosphorus Halides

22. Ester Formation from Alcohols

23. Haloform Reaction
Methyl carbinol cleavage to give Carboxylic acids and Haloform

24. Physical properties High boiling points
Alcohols consist of two parts, an alkyl group and a hydroxyl group. Due to which they have following properties:
High boiling points
They are capable to form hydrogen bonds.

25. Distinction between 1°, 2° and 3° alcohols
Victor–Meyer test
1° alcohols
blood red colouration
2° alcohols
blue colouration
3° alcohols does not react.

26. Lucas test Lucas reagent
conc.hydrochloric acid and anhydrous zinc chloride.

27. Lucas test
Immediate reaction

28. Illustrative example H+
Cyclobutyl bromide on reaction with Mg / dry ether forms an organometallic (A) The organometallic reacts with ethanol to give an alcohol (B) With an equivalent amount of HBr gives 1–bromo–1–methyl cyclopentane (C) Write the structures of (A),(B) and (C) and explain how (C) is obtained from (B).
Solution H+ + +

29. Solution
Ring transformation + +
20 cation
30 cation