Octet

Octet / Reagents

Lithium Aluminum Hydride

Lithium Aluminum Hydride (LiAlH₄) - reducing reagent. Strong reduction of most carbonyl compounds. Common uses: Aldehyde → Primary alcohol, Ketone → Secondary alcohol, Ester → Two alcohols, Carboxylic acid → Primary alcohol, Amide → Amine, Nitrile → Primary a...

Reducing

Reagent details

Name

Lithium Aluminum Hydride

Formula

LiAlH₄

Smiles

[Li+].[AlH4-]

Category

Reducing

Function

Strong reduction of most carbonyl compounds

Common Uses

  1. Aldehyde → Primary alcohol

  2. Ketone → Secondary alcohol

  3. Ester → Two alcohols

  4. Carboxylic acid → Primary alcohol

  5. Amide → Amine

  6. Nitrile → Primary amine

Notes

Very reactive! Violently reacts with water. Use anhydrous ether or THF. Quench carefully with water.

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Reagents

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Sodium Borohydride

Sodium Borohydride (NaBH₄) - reducing reagent. Mild reduction of aldehydes and ketones to alcohols. Common uses: Aldehyde → Primary alcohol, Ketone → Secondary alcohol. Does NOT reduce esters, amides, carboxylic acids, or C=C bonds. Works in protic solvents (...

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DIBAL-H

DIBAL-H ((i-Bu)₂AlH) - reducing reagent. Partial reduction of esters to aldehydes. Common uses: Ester → Aldehyde (at -78°C), Nitrile → Aldehyde (via imine). Temperature critical! At -78°C stops at aldehyde. Warmer or excess gives alcohol.

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H₂/Pd (Catalytic Hydrogenation)

H₂/Pd (Catalytic Hydrogenation) (H₂ + Pd/C) - reducing reagent. Reduction of C=C, C≡C, and some functional groups. Common uses: Alkene → Alkane, Alkyne → Alkane, Nitro → Amine (ArNO₂ → ArNH₂), Benzyl groups removed (hydrogenolysis). Syn addition. Also works w...

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Lindlar Catalyst

Lindlar Catalyst (Pd/CaCO₃/Pb) - reducing reagent. Partial reduction of alkynes to cis-alkenes. Common uses: Alkyne → cis-Alkene (stops at alkene). Poisoned catalyst - lead prevents over-reduction. Syn addition gives cis product.

Reducing

Dissolving Metal (Na/NH₃)

Dissolving Metal (Na/NH₃) (Na + NH₃(l)) - reducing reagent. Reduction of alkynes to trans-alkenes. Common uses: Alkyne → trans-Alkene. Birch reduction conditions. Liquid ammonia at -33°C. Radical mechanism gives trans product.

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Clemmensen Reduction

Clemmensen Reduction (Zn(Hg) + HCl) - reducing reagent. Complete reduction of C=O to CH₂. Common uses: Ketone/Aldehyde → Alkane. Acidic conditions. For acid-sensitive compounds, use Wolff-Kishner instead.

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