Octet

Octet / Reagents

Mercuric Acetate

Mercuric Acetate (Hg(OAc)₂) - other reagent. Oxymercuration reagent. Common uses: Oxymercuration-demercuration (Markovnikov alcohol, no rearrangement). Followed by NaBH₄ to remove Hg. Gives Markovnikov product without carbocation.

Other

Reagent details

Name

Mercuric Acetate

Formula

Hg(OAc)₂

Category

Other

Function

Oxymercuration reagent

Common Uses

  1. Oxymercuration-demercuration (Markovnikov alcohol, no rearrangement)

Notes

Followed by NaBH₄ to remove Hg. Gives Markovnikov product without carbocation.

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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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