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Organic ChemistryKetones and Aldehydes
Diah Agustina Puspitasari, ST., MT
Chemical Engineering Department
Engineering Faculty of Brawijaya University
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Carbonyl Compounds
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Structure of The Carbonyl Group
Carbon is sp2 hybridized.
C=O bond is shorter, stronger, and
more polar than C=C bond in alkenes.
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IUPAC Names forKetones
Replace -ewith -one.
Indicate the position of the carbonyl witha number.
Number the chain so that carbonyl carbonhas the lowest number.
For cyclic ketones the carbonyl carbon is
assigned the number 1.
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Examples
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Naming Aldehydes
Systematic names for aldehydes are derived byreplacing the final e af the alkane with al.
An aldehydes carbon is at the end of a chain, soit number 1.
If the aldehydes group is attached to a largeunit (usually a ring), the suffix carbaldehyde isused.
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Examples
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Common Names of Aldehydes
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Boiling Points
More polar, so higher boiling point thancomparable alkane or ether.
Ketone and aldehydes have no O-H bond so theirmolecules cant form hydrogen bonds with eachother.
The boiling points are lower than alcohol
Chapter 18 9
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Solubility
Good solvent for alcohols. Lone pair of electrons on oxygen of
carbonyl can accept a hydrogen bond
from O-H or N-H. Acetone and acetaldehyde are misible in
water.
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PhysicalPropertiesof Ketones and Aldehydes
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Formaldehyde
Gas at room temperature.
Formalin is a 40% aqueous solution.
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Industrial Importance
Solvents.
Polymers like Bakelite, phenol-formaldehydes resins, urea-formaldehydes glues, etc.
as a starting material in themanufcature of acetic acid, polymer and
drug. Flavorings and additives like vanilla,
cinnamon, artificial butter.
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Ketone and aldehydes inHouse Hold Product
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Syntheses of Ketoneand Aldehydes
Oxidation alcohols.
Ozonolysis of alkenes.
Syntheses of ketone using organolithium
reagents with carboxylic. Aldehyde syntheses by reduction of acid
chlorides.
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A. Oxidation Alcohols
Secondary alcohols ketones
Primary alcohols aldehydes
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B. Ozonolysis of alkenes
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C. Syntheses of ketone usingorganolithium reagents with
carboxylic.
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D Ald h d h b d i f
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D. Aldehyde syntheses by reduction ofacid chlorides.
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Reaction of Ketones andAldehydes
Addition of organometalic reagent.
Reduction reaction.
Hydration.
Oxidation of aldehydes.
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dd f l
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a. Addition of organometalicreagent
Addition to Aldehydes:
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Addition to Aldehydes:Formation of Secondary
Alcohols
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Addi i K
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Addition to Ketones:Formation of Tertiary
Alcohols
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b. Reduction Reaction
Ketones and aldehydes are most commonlyreduced by sodium borohydride.
NaBH4 reduced ketone to secondary alcohols
and aldehydes to primary alcohol
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In an aqueous solution, a ketone or analdehyde is in equilibrium with its hydrate, ageminal diol.
Hydration occurs through the nucleophilicaddition mechanism, with water (in acid) or
hydroxide ion (in base) serving as thenucleophile.
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c. Hydration
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Hydration of ketones and aldehydes
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d. Oxidation ofaldehydes