Octet

Octet / Reagents

LDA (Lithium Diisopropylamide)

LDA (Lithium Diisopropylamide) (LiN(i-Pr)₂) - base reagent. Very strong, non-nucleophilic base for enolate formation. Common uses: Quantitative enolate formation, Kinetic vs thermodynamic enolate control, α-Deprotonation of carbonyl compounds. pKa ~36 (conjug...

Base

Reagent details

Name

LDA (Lithium Diisopropylamide)

Formula

LiN(i-Pr)₂

Category

Base

Function

Very strong, non-nucleophilic base for enolate formation

Common Uses

  1. Quantitative enolate formation

  2. Kinetic vs thermodynamic enolate control

  3. α-Deprotonation of carbonyl compounds

Notes

pKa ~36 (conjugate acid). Forms enolates irreversibly. Use at -78°C in THF.

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Reagents

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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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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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