Ketones and Aldehydes

Diah Agustina Puspitasari, ST., MT Chemical Engineering Department Engineering Faculty of Brawijaya University

Organic Chemistry

Carbonyl Compounds

Structure of The Carbonyl Group

Carbon is sp2 hybridized. C=O bond is shorter, stronger, and more polar than C=C bond in alkenes.

IUPAC Names for Ketones

Replace -e with -one. Indicate the position of the carbonyl with a number. Number the chain so that carbonyl carbon has the lowest number. For cyclic ketones the carbonyl carbon is assigned the number 1.

Examples

Naming Aldehydes
Systematic names for aldehydes are derived by replacing the final e af the alkane with al. An aldehydes carbon is at the end of a chain, so it number 1. If the aldehydes group is attached to a large unit (usually a ring), the suffix carbaldehyde is used.

Examples

Common Names of Aldehydes

Boiling Points
More polar, so higher boiling point than comparable alkane or ether. Ketone and aldehydes have no O-H bond so their molecules cant form hydrogen bonds with each other. The boiling points are lower than alcohol

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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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PhysicalProperties of 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, phenolformaldehydes resins, ureaformaldehydes glues, etc. as a starting material in the manufcature of acetic acid, polymer and drug. Flavorings and additives like vanilla, cinnamon, artificial butter.
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Ketone and aldehydes in House Hold Product

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Syntheses of Ketone and 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 using organolithium reagents with carboxylic.

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D. Aldehyde syntheses by reduction of acid chlorides.

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Reaction of Ketones and Aldehydes

Addition of organometalic reagent. Reduction reaction. Hydration. Oxidation of aldehydes.

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a. Addition of organometalic reagent

Addition to Aldehydes: Formation of Secondary Alcohols

Addition to Ketones: Formation of Tertiary Alcohols

b. Reduction Reaction
Ketones and aldehydes are most commonly reduced by sodium borohydride. NaBH4 reduced ketone to secondary alcohols and aldehydes to primary alcohol

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c. Hydration
In an aqueous solution, a ketone or an aldehyde is in equilibrium with its hydrate, a geminal diol. Hydration occurs through the nucleophilic addition mechanism, with water (in acid) or hydroxide ion (in base) serving as the nucleophile.

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Hydration of ketones and aldehydes

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d. Oxidation of aldehydes

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