Octet

Octet / Reagents

Sodium Cyanide

Sodium Cyanide (NaCN) - nucleophile reagent. Carbon nucleophile for SN2. Common uses: SN2 to make nitriles (adds one carbon), Nitrile can be hydrolyzed to carboxylic acid. Highly toxic! Nitrile product is versatile synthetic intermediate.

Nucleophile

Reagent details

Name

Sodium Cyanide

Formula

NaCN

Smiles

[Na+].[C-]#N

Category

Nucleophile

Function

Carbon nucleophile for SN2

Common Uses

  1. SN2 to make nitriles (adds one carbon)

  2. Nitrile can be hydrolyzed to carboxylic acid

Notes

Highly toxic! Nitrile product is versatile synthetic intermediate.

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Reagents

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Lithium Aluminum Hydride

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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.

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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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