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BÀI GIẢNG ORGANIC CHEMISTRY chapter10

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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Chapter 10:

ALCOHOLS-PHENOLS

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NOMENCLATURE OF ALCOHOLS
Common names: alkyl + alcohol

IUPAC names: hydrocarbon + ol


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PREPARATION OF ALCOHOLS
Alcohols from alkenes

Markovnikov’s rule

H2SO4, H3PO4…
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Anti-Markovnikov

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Alcohols from alkyl halides

Carbocation rearrangements may occur
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Alcohols from aldehydes & ketones

Aldehydes & ketones can also be reduced using
LiAlH4, H2/Pt, Pd, Ni, Ru …
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Alcohols from carboxylic acids & derivatives

Can NOT use NaBH4, H2/Pt, Pd, Ni, Ru… for acids


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Alcohols from Grignard reagents

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REACTIONS OF ALCOHOLS
Reactions of proton in -OH

Can NOT react with NaOH

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Dehydration reactions

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isomerization
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Primary alcohol

Internal alkene
1-alkenes can NOT be prepared using the
dehydration reaction

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Conversion of alcohols to alkyl halides
Only in acidic conditions

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isomerization

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PCl3,
SOCl2
… can
also be
used

NO carbocation formation,
NO rearrangement

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Can NOT work for tertiary alcohols due to steric hindrance


Conversion of alcohols to ethers

Only for
symmetric ether

Only effective for primary alcohols

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Reaction mechanism:

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Fisher esterification reactions
Need acid catalyst

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Reaction mechanism:

Reversible reaction

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Oxidation reactions

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Can NOT be isolated

PCC: pyridinium chlorochromate
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PHENOLS
SP2 Carbon

SP3 Carbon

Some
naturally
occurring
phenols
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