Chapter 10: ALCOHOLS-PHENOLS pps

NOMENCLATURE OF ALCOHOLS Common names: alkyl + alcohol IUPAC names: hydrocarbon + ol... Alcohols from alkyl halidesCarbocation rearrangements may occur... Alcohols from carboxylic acids

ORGANIC CHEMISTRY

Dr Nam T S Phan Faculty of Chemical Engineering

HCMC University of Technology

Office: room 211, B2 Building Phone: 8647256 ext 5681 Email: ptsnam@hcmut.edu.vn

Chapter 10 : ALCOHOLS-PHENOLS

NOMENCLATURE OF ALCOHOLS

Common names: alkyl + alcohol

IUPAC names: hydrocarbon + ol

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PREPARATION OF ALCOHOLS

Alcohols from alkenes

H 2 SO 4 , H 3 PO 4 …

Markovnikov’s rule

Anti-Markovnikov

Alcohols from alkyl halides

Carbocation rearrangements may occur

Alcohols from aldehydes & ketones

Aldehydes & ketones can also be reduced using

LiAlH 4 , H 2 /Pt, Pd, Ni, Ru …

Alcohols from carboxylic acids & derivatives

Can NOT use NaBH , H /Pt, Pd, Ni, Ru… for acids

Alcohols from Grignard reagents

REACTIONS OF ALCOHOLS

Reactions of proton in -OH

Can NOT react with NaOH

Dehydration reactions

isomerization

Only in acidic conditions

Conversion of alcohols to alkyl halides

isomerization

PCl 3 , SOCl 2

… can also be used

NO carbocation formation,

NO rearrangement

Conversion of alcohols to ethers

Only effective for primary alcohols

Only for symmetric ether

Reaction mechanism:

Fisher esterification reactions

Need acid catalyst

Reversible reaction

Reaction mechanism:

Oxidation reactions

Can NOT be isolated

PCC: pyridinium chlorochromate

NOMENCLATURE OF PHENOLS

PREPARATION OF PHENOLS

O-acylations of phenols

NO Lewis acid

The Kolbe-Schmitt reaction

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Preparation of aryl ethers

Can NOT prepare aryl ether directly from the

reaction of phenol & alcohol in the presence

Cleavage of aryl ethers by hydrogen halides

Reaction

mechanism:

NOTE:

S N 2

Oxidation of

phenols

Polymerization with formaldehyde

Electrophilic aromatic substitution reactions

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