Octet

Octet / Reagents

Sodium Hydride

Sodium Hydride (NaH) - base reagent. Strong base (deprotonation), poor nucleophile. Common uses: Deprotonation of alcohols to alkoxides, Deprotonation of active methylene compounds, Williamson ether synthesis. Not a reducing agent in practice! Just a base. H₂...

Base

Reagent details

Name

Sodium Hydride

Formula

NaH

Smiles

[Na+].[H-]

Category

Base

Function

Strong base (deprotonation), poor nucleophile

Common Uses

  1. Deprotonation of alcohols to alkoxides

  2. Deprotonation of active methylene compounds

  3. Williamson ether synthesis

Notes

Not a reducing agent in practice! Just a base. H₂ gas evolved.

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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 (...

Reducing

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

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.

Reducing

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...

Reducing

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.

Reducing

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