Chemistry - Ketone and Aldehydes

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17 Terms

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Jones Oxidation (Na₂Cr₂O₇)

Strong oxidation of aldehydes → carboxylic acids.
Strong oxidation of 1° alcohols → carboxylic acids.
2° alcohols → ketones.
Cannot stop at aldehyde; pushes fully to acid.
Acetone is solvent.

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NaBH₄ Reduction (NaBH₄, EtOH)

Reduces aldehydes & ketones → alcohols.
Does not reduce esters, amides, or carboxylic acids.
Safe with protic solvents (EtOH, MeOH).
Selective for carbonyls in complex molecules.

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KMnO₄ Oxidation (KMnO₄, heat)

Strong oxidation: aldehydes/1° alcohols → acids.
2° alcohols → ketones.
Cleaves alkenes → carbonyls or acids.
Very aggressive, over-oxidation common.

<ul><li><p>Strong oxidation: aldehydes/1° alcohols → <strong>acids</strong>.</p></li><li><p>2° alcohols → <strong>ketones</strong>.</p></li><li><p>Cleaves alkenes → carbonyls or acids.</p></li><li><p>Very aggressive, over-oxidation common.</p></li></ul><p></p>

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PCC Oxidation (PCC with solvent CH₂Cl₂)

1° alcohols → aldehydes (no over-oxidation).
2° alcohols → ketones.
Works under anhydrous conditions.
Milder than Jones/KMnO₄.

<ul><li><p>1° alcohols → <strong>aldehydes</strong> (no over-oxidation).</p></li><li><p>2° alcohols → <strong>ketones</strong>.</p></li><li><p>Works under anhydrous conditions.</p></li><li><p>Milder than Jones/KMnO₄.</p></li></ul><p></p>

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Swern Oxidation (DMSO, (COCl)₂, Et₃N)

1° alcohols → aldehydes.
2° alcohols → ketones.
No heavy metals.
Cold (–78°C) required.

<ul><li><p>1° alcohols → <strong>aldehydes</strong>.</p></li><li><p>2° alcohols → <strong>ketones</strong>.</p></li><li><p>No heavy metals.</p></li><li><p>Cold (–78°C) required.</p></li></ul><p></p>

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Ozonolysis (O₃ → Zn/HCl or DMS)

Cleaves alkenes → two carbonyls.
Reductive workup → aldehydes/ketones.
Oxidative workup → acids/ketones.
Exact cleavage of double bond.

<ul><li><p>Cleaves alkenes → <strong>two carbonyls</strong>.</p></li><li><p>Reductive workup → aldehydes/ketones.</p></li><li><p>Oxidative workup → acids/ketones.</p></li><li><p>Exact cleavage of double bond.</p></li></ul><p></p>

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LiAlH₄ Reduction (1. LiAlH₄ 2. H₃O⁺)

Reduces aldehydes → 1° alcohols.
Reduces ketones → 2° alcohols.
Reduces esters/acids/amides → alcohols/amines.
Must be quenched carefully with water after reaction.

<ul><li><p>Reduces <strong>aldehydes → 1° alcohols</strong>.</p></li><li><p>Reduces <strong>ketones → 2° alcohols</strong>.</p></li><li><p>Reduces <strong>esters/acids/amides → alcohols/amines</strong>.</p></li><li><p>Must be quenched carefully with water after reaction.</p></li></ul><p></p>

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Grignard (1. R–MgBr 2. H₃O⁺)

Nucleophilic R⁻ attack on carbonyl carbon.
Aldehydes → 2° alcohols (add one R).
Ketones → 3° alcohols (add one R).
Adds C–C bonds (key carbon chain-building reaction).

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Tollens Oxidation (Ag₂O, OH⁻ → H₃O⁺)

Selective aldehyde oxidation → carboxylate → acid.
Leaves alcohols/ketones unchanged.
Produces silver mirror.
Mild & chemoselective.

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Wittig Reaction (Ph₃P=CH₂)

Converts carbonyl C=O → C=C.
Aldehydes → terminal alkenes with =CH₂.
Replaces oxygen entirely.
Good for stereoselective alkene formation; opposite of ozonolysis.

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Weak Hydride Reduction (LTBA) (Li(t-BuO)₃, cold)

Selective reduction of acid chlorides → aldehydes.
Stops before alcohol stage.
Requires cold conditions (–78°C).
More selective than LiAlH₄.

<ul><li><p>Selective reduction of <strong>acid chlorides → aldehydes</strong>.</p></li><li><p>Stops before alcohol stage.</p></li><li><p>Requires cold conditions (–78°C).</p></li><li><p>More selective than LiAlH₄.</p></li></ul><p></p>

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DIBAL-H Reduction (DIBAL-H → H₃O⁺)

Esters → aldehydes (controlled low temp).
Excess/warm → alcohols.
Nitriles → aldehydes (via imine).
Temperature-sensitive.

<ul><li><p>Esters → <strong>aldehydes</strong> (controlled low temp).</p></li><li><p>Excess/warm → alcohols.</p></li><li><p>Nitriles → aldehydes (via imine).</p></li><li><p>Temperature-sensitive.</p></li></ul><p></p>

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Friedel–Crafts Acylation (RCOCl, AlCl₃)

Benzene → aryl ketone.
No rearrangements.
Product deactivates the ring.
Clean one-substitution reaction.

<ul><li><p>Benzene → <strong>aryl ketone</strong>.</p></li><li><p>No rearrangements.</p></li><li><p>Product deactivates the ring.</p></li><li><p>Clean one-substitution reaction.</p></li></ul><p></p>

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Alkyne Hydration (HgSO₄, H₂SO₄, H₂O)

Terminal alkyne → methyl ketone (Markovnikov).
Proceeds via enol → keto.
Needs Hg²⁺ catalyst.
Internal alkynes → ketones.

<ul><li><p>Terminal alkyne → <strong>methyl ketone</strong> (Markovnikov).</p></li><li><p>Proceeds via enol → keto.</p></li><li><p>Needs Hg²⁺ catalyst.</p></li><li><p>Internal alkynes → ketones.</p></li></ul><p></p>

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General Acetal Formation (2 ROH, H⁺)

Carbonyl → acetal (protected form).
Hemiacetal intermediate.
Stable in base.
Deprotected with aqueous acid.

<ul><li><p>Carbonyl → <strong>acetal</strong> (protected form).</p></li><li><p>Hemiacetal intermediate.</p></li><li><p>Stable in base.</p></li><li><p>Deprotected with aqueous acid.</p></li></ul><p></p>

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Cyclic Acetal Formation (with diol) (HOCH₂CH₂OH, cat. H⁺)

Carbonyl + diol → 5-membered cyclic acetal.
Excellent protecting group.
Stable in base, removable in acid.
Driven by intramolecular ring closure.

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Hydrazone Formation (PhNHNH₂, pH 4–5)

Carbonyl → C=N–NHPh (hydrazone).
Dehydration product from hydrazine/hydrazide reacting with an aldehyde or ketone.
Formed via condensation (loss of H₂O).
Product = hydrazone: Carbonyl oxygen replaced by =N–NHPh (or =N–NH₂ for hydrazine).