BÀI GIẢNG ORGANIC CHEMISTRY chapter10

NOMENCLATURE OF ALCOHOLS Common names: alkyl + alcohol IUPAC names: hydrocarbon + ol... Alcohols from alkyl halides Carbocation rearrangements may occur... REACTIONS OF ALCOHOLS Reaction

ORGANIC CHEMISTRY

Dr Nam T S Phan Faculty of Chemical Engineering

HCMC University of Technology

Office: room 211, B2 Building Phone: 38647256 ext 5681 Email: ptsnam@hcmut.edu.vn

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NOMENCLATURE OF ALCOHOLS

Common names: alkyl + alcohol

IUPAC names: hydrocarbon + ol

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PREPARATION OF ALCOHOLSAlcohols 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 4 , H 2 /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

Can NOT work for tertiary alcohols due to steric hindrance

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

of acid catalyst

Cleavage of aryl ethers by hydrogen halides

Oxidation of

phenols

Polymerization with formaldehyde

Electrophilic aromatic substitution reactions

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