ORIENT COLLEGES TALAGANG

Organic Chemistry (BSc-II)

On-Screen Lectures
Aldehydes & Ketones
Lecture # 3
 Reactions of Aldehydes & Ketones

Addition of Ammonia & Its Derivatives

Aldehydes & ketones add an ammonia or its
derivatives’ molecule across their carbonyl group
to form condensation products containing C=N
bond

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 Reactions of Aldehydes & Ketones

The general form of reactions is

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 Reactions of Aldehydes & Ketones

Addition of Ammonia
Aldehydes & ketones reacts with ammonia and
form imines
Imines are compounds that contain C=N bond

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 Reactions of Aldehydes & Ketones

Addition of primary amines

Aldehydes & ketones reacts with primary amines
and form imines

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 Reactions of Aldehydes & Ketones

Addition of hydroxylamine
Aldehydes & ketones reacts with hydroxylamine
and form oximes
Imines are compounds that contain C=N-OH
bond

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 Reactions of Aldehydes & Ketones

Addition of hydrazine
Aldehydes & ketones reacts with hydrazine and
form hydrazones
Hydrazones are compounds that contain C=N-NH2 bond

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 Reactions of Aldehydes & Ketones

Addition of Phenylhydrazine
Aldehydes & ketones reacts with phenylhydrazine
and form phenylhydrazones
Phenylhydrazones are compounds that contain
C=N-NH-C6H5 bond

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 Reactions of Aldehydes & Ketones

Addition of Semicarbazide
Aldehydes & ketones reacts with semicarbazide
and form semicarbazones
Semicarbazones are compounds that contain
C=N-NH-CONH2 group

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 Reactions of Aldehydes & Ketones
Addition of 2,4-dinitrophenylhydrazine (2,4-DNPH)
Aldehydes & ketones reacts with 2,4-
dinitrophenylhydrazine (2,4-DNPH) and form 2,4-
dinitrophenylhydrazones

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 Reactions of Aldehydes & Ketones

Addition of Ammonia & Its Derivatives:

Mechanism

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 Reactions of Aldehydes & Ketones

Assignment 1
Write reactions of (i) acetaldehyde (ii) acetone (iii) benzaldehyde with
following
 Ethylamine
 Hydrazine
 Semicarbazide
 Phenylhydrazine

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 Reactions of Aldehydes & Ketones

Assignment 2
Write mechanisms for following reactions
 Ethylamine and ammonia
 Hydrazine and acetone
 Semicarbazide and acetaldehyde
 Phenylhydrazine and benzaldehyde

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 Reactions of Aldehydes & Ketones
Addition of Hydrogen Cyanide (HCN)
Aldehydes & ketones reacts HCN and form
cyanohydrins. These cyanohydrins when hydrolyzed give
α-hydroxyacids
 α-hydroxyacids are those carboxylic acids that contain
an –OH group at α-Carbon

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 Reactions of Aldehydes & Ketones
Addition of Hydrogen Cyanide (HCN)

HCN is a toxic gas therefore it is prepared in situ by

reacting NaCN with HCl or H2SO4

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 Reactions of Aldehydes & Ketones
Addition of Hydrogen Cyanide (HCN): Mechanism

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 Reactions of Aldehydes & Ketones
Addition of Hydrogen Cyanide (HCN)
When cyanohydrins when hydrolyzed give α-
hydroxyacids

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 Reactions of Aldehydes & Ketones
Addition of Hydrogen Cyanide (HCN): Mechanism

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 Reactions of Aldehydes & Ketones
Addition of sodium Bisulphite (NaHSO3)
Aldehydes & ketones reacts NaHSO3 and form addition
products. These adducts are white crystalline solids

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 Reactions of Aldehydes & Ketones
Addition of sodium Bisulphite (NaHSO3): Mechanism

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 Reactions of Aldehydes & Ketones
Addition of sodium Bisulphite (NaHSO3)
These products when treated with a mineral acid, give
back carbonyl compound. Thus they can be used to
separate, purify and identify carbonyl compounds

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 Reactions of Aldehydes & Ketones
Reformatsky Reaction
Reformatsky reaction is reaction of aldehydes and
ketones with an α-bromoester in the presence of Zn to
form β-hydroxyester

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 Reactions of Aldehydes & Ketones
Reformatsky
Reaction:
Mechanism

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 Reactions of Aldehydes & Ketones
Reformatsky Reaction: Another example

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