ALDEHYDES & KETONES

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Definition of Aldehydes and Ketones

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1

Definition of Aldehydes and Ketones

Compounds containing a carbonyl group (C=OC=O).

Aldehydes: RCHORCHO.

Ketones: R1COR2R_1COR_2.

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2

Carbonyl Group Characteristics

Composed of a sigma (σ\sigma) and pi (π\pi) bond. Polar due to oxygen's electronegativity.

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3

Naming Aldehydes

Replace "-e" of parent alkane with "-al" (e.g., methanal).

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4

Naming Ketones

Replace "-e" of parent alkane with "-one" (e.g., propanone).

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5

Physical Properties of Carbonyl Compounds (Aldehyde & Ketone)

Higher boiling points than alkanes, lower than alcohols.

Soluble in water up to 2–3 carbons due to hydrogen bonding.

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Preparation of Carbonyl Compounds: Alcohol Oxidation

Primary alcohols → Aldehydes (mild oxidants like PCC).

Secondary alcohols → Ketones.

<p>Primary alcohols → Aldehydes (mild oxidants like PCC).</p><p>Secondary alcohols → Ketones.</p>
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7

Preparation of Carbonyl Compounds: Ozonolysis of Alkenes

Cleavage forms aldehydes and ketones depending on substitution.

<p><span>Cleavage forms aldehydes and ketones depending on substitution.</span></p>
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8

Preparation of Carbonyl Compounds: Hydration of Alkynes

Terminal alkynes react with water (Hg2+^{2+}, acid catalyst) to form ketones.

<p><span>Terminal alkynes react with water (Hg2+^{2+}, acid catalyst) to form ketones.</span></p>
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Nucleophilic Addition Reactions

Carbonyl carbon (δ+) attracts nucleophiles, breaking the π bond.

<p><span>Carbonyl carbon (δ+) attracts nucleophiles, breaking the π bond.</span></p>
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Hydration of Aldehydes and Ketones

Forms geminal diols (e.g., chloral hydrate, a hypnotic).

<p><span>Forms geminal diols (e.g., chloral hydrate, a hypnotic).</span></p>
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Cyanohydrin Formation

Reaction with HCN produces cyanohydrins, used in synthesizing α-hydroxy acids.

<p><span>Reaction with HCN produces cyanohydrins, used in synthesizing α-hydroxy acids.</span></p>
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12

Sodium Hydrogen Sulfite Addition

Forms crystalline addition products for purification of lower aldehydes and ketones.

<p>Forms crystalline addition products for purification of lower aldehydes and ketones.</p>
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Reduction of Carbonyls//Addition of hydride

Aldehydes → Primary alcohols, Ketones → Secondary alcohols (reagents: NaBH4,LiAlH4).

<p>Aldehydes → Primary alcohols, Ketones → Secondary alcohols (reagents: NaBH4,LiAlH4).</p>
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14

Grignard Reagents

React with aldehydes and ketones to produce alcohols.

<p>React with aldehydes and ketones to produce alcohols.</p>
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15

Polymerization of Formaldehyde

Forms paraformaldehyde (solid) and paraldehyde (liquid hypnotic).

<p><span>Forms paraformaldehyde (solid) and paraldehyde (liquid hypnotic).</span></p>
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Hemiacetal and Acetal Formation

Aldehydes react with alcohols to form hemiacetals; further reaction produces acetals.

<p><span>Aldehydes react with alcohols to form hemiacetals; further reaction produces acetals.</span></p>
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Keto-Enol Tautomerism

Carbonyl compounds exist in equilibrium with their enol form.

<p><span>Carbonyl compounds exist in equilibrium with their enol form.</span></p>
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Haloform Reaction

Methyl ketones react with halogens (e.g., iodine) to form haloforms (positive iodoform test).

<p><span>Methyl ketones react with halogens (e.g., iodine) to form haloforms (positive iodoform test).</span></p>
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19

Aldol Condensation

Enolate ions react with aldehydes to form β-hydroxy aldehydes, which dehydrate to α,β-unsaturated compounds.

<p><span>Enolate ions react with aldehydes to form β-hydroxy aldehydes, which dehydrate to α,β-unsaturated compounds.</span></p>
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20

Aldehyde Oxidation

Oxidized to carboxylic acids by mild oxidants (e.g., KMnO4).

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21

Drug Metabolism of Aldehydes

Catalyzed by enzymes like aldehyde dehydrogenase.

<p><span>Catalyzed by enzymes like aldehyde dehydrogenase.</span></p>
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22

Sugar Cyclization

Intramolecular hemiacetals form stable cyclic structures (e.g., glucose as pyranose).

<p><span>Intramolecular hemiacetals form stable cyclic structures (e.g., glucose as pyranose).</span></p>
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23

Mutarotation of Sugars

Interconversion between anomers (α and β) in solution, changing optical rotation.

<p><span>Interconversion between anomers (α and β) in solution, changing optical rotation.</span></p>
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24

Addition of Amines

Primary amines react with aldehydes to form imines, intermediates in organic synthesis.

<p><span>Primary amines react with aldehydes to form imines, intermediates in organic synthesis.</span></p>
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Oxime Formation

Aldehydes react with hydroxylamine to form oximes, useful for characterization.

<p><span>Aldehydes react with hydroxylamine to form oximes, useful for characterization.</span></p>
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