Reagents

Flashcards covering key organic chemistry reagents, their classifications, and applications.

H_3O^+

Strong acid; protonates alkenes/alcohols; used in hydration and dehydration.

H2SO4

Strong acid; used for dehydration of alcohols to form alkenes.

H3PO4

Acid catalyst; involved in dehydration and esterification.

CH3CO2H (AcOH)

Weak acid; used in esterification with alcohols.

HBr / HCl

Strong acids; act as electrophiles in hydrohalogenation of alkenes (Markovnikov addition).

NaOH

Strong base/nucleophile; used in SN2 substitution and E2 elimination reactions.

KOtBu

Bulky base; facilitates E2 elimination, yielding the Hofmann product.

Pyridine

Weak base; neutralizes acids, commonly used with TsCl.

TsCl

Converts OH groups into tosylates for better leaving groups.

NaOR

Alkoxide; used in ether synthesis via the Williamson ether synthesis.

NaNH_2

Very strong base; deprotonates terminal alkynes.

NaH

Strong base; generates alkoxides.

NH_3

Weak nucleophile; utilized in SN2 substitution reactions.

NaSH

Nucleophile; forms thiols.

NaN_3

Nucleophile; creates azides, which can lead to amines.

NaCN

Nucleophile; yields nitriles.

NaX

Halide nucleophile; participates in SN1/SN2 substitution reactions.

RMgBr (Grignard)

Strong nucleophile; adds to carbonyls forming alcohols.

RLi

Strong nucleophile; adds to carbonyls to produce alcohols.

RCCNa

Acetylide nucleophile; adds to carbonyls and allows for alkylation.

LiAlH_4

Strong reducing agent; reduces esters, acids, ketones, and aldehydes.

NaBH_4

Milder reducing agent; reduces ketones and aldehydes.

Pd / Pt

Catalysts; used for hydrogenation of alkenes and alkynes.

Lindlar’s Catalyst

Catalyst for partial hydrogenation, resulting in cis-alkenes.

H_2

Reducing agent; facilitates hydrogenation of alkenes and alkynes.

BH_3-THF

Reagent for hydroboration, yielding anti-Markovnikov alcohols.

Sia_2BH

Sterically hindered hydroboration agent; produces selective alcohol formation.

H2O2

Oxidant that completes hydroboration-oxidation.

PCC

Mild oxidant; converts alcohols into aldehydes.

Na2Cr2O_7

Strong oxidant; converts alcohols into carboxylic acids.

NaOCl / TEMPO

Controlled oxidants; convert alcohols to carbonyls.

KMnO4 / OsO4

Used for dihydroxylation of alkenes.

O_3

Ozonolysis agent; cleaves double bonds.

m-CPBA / CH3CO3H

Peracids; used for the epoxidation of alkenes.

Cl2 / Br2

Electrophiles; facilitate halogenation of alkenes (anti addition).

DMF, DMSO, CH_3CN, acetone

Polar aprotic solvents; favor SN2 reactions.

Et2O, THF, CH2Cl2, CHCl3

Nonpolar/protic solvents; favor SN1 reactions.