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BÀI GIẢNG ORGANIC CHEMISTRY chapter11

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 11:
C=O

ALDEHYDES-KETONES
C=C

SP2 carbon
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NOMENCLATURE OF ALDEHYDES

Common names: carboxylic acid Æ “aldehyde”
is substituted for “ic acid”

IUPAC names: hydrocarbon + al

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Lower priority than ester Æ “oxo” group

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NOMENCLATURE OF KETONES
Derived names: alkyls + ketone

IUPAC names: hydrocarbon + one

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PREPARATION OF ALDEHYDES &
KETONES

Aldehydes & ketones from alkenes

In the presence of an oxidizing agent, the products
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will be ketones / carboxylic acids


Aldehydes & ketones from alkynes
Markovnikov’s rule


Anti-Markovnikov
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Aldehydes & ketones from alcohols

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Can NOT be isolated

PCC: pyridinium chlorochromate
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Aldehydes from esters, acyl chlorides

Note: LiAlH4 Æ alcohols

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Preparation of aromatic ketones

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Gatterman-Koch synthesis of benzaldehyde

Can NOT be
prepared &
isolated
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REACTIONS OF ALDEHYDES &
KETONES I

The partial positive
carbon can be attacked
by nucleophiles

The addition of nucleophiles to the carbon
atom of the carbonyl group in nucleophilic
addition reactions
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Reactions with Grignard reagents

Only for the reaction of HCHO
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Numbers 1 & 2 are used to indicate that the acid is not added
until the reaction with the Grignard reagent is complete

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Reactions with acetylide ions

Weak acid, will NOT react with the triple bond

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Reactions with hydrogen cyanide

Converted back to carbonyl in basic solutions

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Nitriles Æ carboxylic acids

Nitriles Æ amines

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Reactions with primary amines

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Reaction mechanism:

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Reactions with secondary amines

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Reaction mechanism:

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Reactions with water

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