Octet

Octet / Reagents

Sodium Methoxide

Sodium Methoxide (NaOCH₃) - base reagent. Strong base and nucleophile. Common uses: E2 elimination, Claisen condensation, Transesterification. Use in MeOH solvent. NaOEt in EtOH is analogous. Also acts as nucleophile in SN2.

Base

Reagent details

Name

Sodium Methoxide

Formula

NaOCH₃

Smiles

[Na+].C[O-]

Category

Base

Function

Strong base and nucleophile

Common Uses

  1. E2 elimination

  2. Claisen condensation

  3. Transesterification

Notes

Use in MeOH solvent. NaOEt in EtOH is analogous. Also acts as nucleophile in SN2.

This is one row of the Reagent guide sheet - print all 63 reagents on one page.

Reagents

Related Content

Source collection

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

Study guides

Related study guides

Free, in-depth guides that put this material in context.

Study reactions without memorizingArrow-pushing basicsSN1 vs SN2 decision guideAll guides