CARBONYL COMPOUNDS
DR SALMIAH JAMAL BINTI MAT ROSID
Chapter outline
6.6.1 Nomenclature and physical properties
6.6.2 Reactions of carbonyl compounds
• Functional group: Carbonyl
• Two classes of carbonyl compounds:
Aldehyde Ketone
RCOH RCOR
R = aliphatic or aromatic
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• Aldehydes are named by replacing the -e of the
corresponding parent alkane with -al
o The aldehyde functional group is always carbon 1 and need not
be numbered
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• Aldehyde functional groups bonded to a ring are
named using the suffix carbaldehyde
o Benzaldehyde is used more commonly than the name
benzenecarbaldehyde
• Practice
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• Ketones are named by replacing the -e of the
corresponding parent alkane with –one
o The parent chain is numbered to give the ketone carbonyl
the lowest possible number
o In common nomenclature simple ketones are named by
preceding the word ketone with the names of both groups
attached to the ketone carbonyl
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• Common names of ketones that are also IUPAC
names are shown below
• Practice
CH3COCH(CH3)CH2CH3
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• Molecules of aldehyde (or ketone) cannot hydrogen
bond to each other
o They rely only on intermolecular dipole-dipole interactions
and therefore have lower boiling points than the
corresponding alcohols
• Aldehydes and ketones can form hydrogen bonds with
water and therefore low molecular weight aldehydes
and ketones have appreciable water solubility
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i. Oxidation of alcohol
• Primary alcohols are oxidized to aldehydes by PCC
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• Secondary alcohols are oxidized to ketones by KMnO4
or K2Cr2O7
K2Cr2O7
H+
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ii. Ozonolysis of Alkenes
• Convert alkene into aldehyde or ketone
• Breaks C=C to form two carbonyl compounds
Aldehydes
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iii. Friedel-Craft Acylation
• To prepare aromatic ketones
• Reaction of benzene and acyl chloride in the presence of AlCl3
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1. Nucleophilic Addition Reactions
• Typical reaction of carbonyl group
• Addition of a nucleophile to a carbonyl C occurs because of the δ+ charge at
theC
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i. Addition of Hydrogen Cyanide
• Reaction of aldehyde or ketone with HCN
• Produce cyanohydrin
Examples:
propanal 2-hydroxybutanenitrile
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ii. Addition of Water
• Reaction of aldehyde or ketone with water (hydration)
• Produce carbonyl hydrates (gem-diols)
ethane-1,1-diol
cyclohexane-1,1-diol
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iii Addition of Alcohols
• Hemiacetal
. o An aldehyde or ketone dissolved in an alcohol will form an
equilibrium mixture containing the corresponding hemiacetal
o A hemiacetal has a hydroxyl and alkoxyl group on the same C
hemiacetal
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hemiketal
• Acetal
o An aldehyde (or ketone) in the presence of excess alcohol
and an acid catalyst will form an acetal
o Formation of the acetal proceeds via the corresponding
hemiacetal
o An acetal has two alkoxyl groups bonded to the same C
hemiacetal acetal
hemiketal ketal 16
iv. Addition of Grignard Reagent
• Carbonyl compounds react with Grignard reagent
• Produce 1°, 2° or 3° alcohol
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2. Reduction Reactions
• Aldehyde and ketone are reduced to 1°and 2° alcohols by
reducing agents
• Reducing agent examples:
o Lithium aluminium hydride (LiAlH4)
o Sodium borohydride (NaBH4)
o Catalytic hydrogenation (Pt or Ni)
Aldehyde 1° alcohol Ketone 2° alcohol
Aldehyde 1° alcohol Ketone 2° alco1h8ol
3. Oxidation Reactions
• Ketone – no H → do not undergo oxidation reaction
• Used to distinguish aldehyde and ketone
• Oxidizing agent examples:
o Na2Cr2O7/H+, K2Cr2O7/H+, KMnO4/H+
o Tollens’ reagent
o Fehling’s reagent
o Schiff reagent
Purple colour of
KMnO4 decolorised
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• Tollens’ Test (Silver Mirror Test)
o The presence of an aldehyde results in formation of a
silver mirror (by oxidation of the aldehyde and reduction
of the silver cation)
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• Fehling’s Reagent
o Cu2+ complex in basic solution
o Aliphatic aldehyde → positive result
o Ketones and benzaldehyde → negative result
• Schiff’s Reagent
o Aqueous solution of fucshin, NaHSO3 and HCl
o Aldehyde → positive result (pink coloration formed)
o Ketones and some aromatic benzaldehyde → negative
result
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Thank You
