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Reagents
Common reagents and usage notes
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All Reagents
Common reagents and usage notes
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 (...
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...
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.
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...
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.
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.
Clemmensen Reduction
Clemmensen Reduction (Zn(Hg) + HCl) - reducing reagent. Complete reduction of C=O to CH₂. Common uses: Ketone/Aldehyde → Alkane. Acidic conditions. For acid-sensitive compounds, use Wolff-Kishner instead.
PCC (Pyridinium Chlorochromate)
PCC (Pyridinium Chlorochromate) (C₅H₅NH⁺CrO₃Cl⁻) - oxidizing reagent. Mild oxidation, stops at aldehyde. Common uses: 1° Alcohol → Aldehyde, 2° Alcohol → Ketone. Anhydrous conditions. Does not over-oxidize to carboxylic acid. CH₂Cl₂ solvent.
Jones Reagent
Jones Reagent (CrO₃/H₂SO₄/H₂O) - oxidizing reagent. Strong oxidation to carboxylic acid. Common uses: 1° Alcohol → Carboxylic acid, 2° Alcohol → Ketone, Aldehyde → Carboxylic acid. Aqueous conditions. 1° alcohols go all the way to carboxylic acid.
Potassium Permanganate
Potassium Permanganate (KMnO₄) - oxidizing reagent. Strong oxidation, varies with conditions. Common uses: Cold, dilute: Alkene → syn-Diol, Hot, concentrated: Alkene → Cleavage to carboxylic acids/ketones, Benzylic oxidation: ArCH₃ → ArCOOH. Purple color. Col...
Osmium Tetroxide
Osmium Tetroxide (OsO₄) - oxidizing reagent. Syn-dihydroxylation of alkenes. Common uses: Alkene → syn-Diol. Very toxic! Use catalytically with NMO (N-methylmorpholine N-oxide) as co-oxidant.
mCPBA
mCPBA (m-ClC₆H₄CO₃H) - oxidizing reagent. Epoxidation of alkenes. Common uses: Alkene → Epoxide, Sulfide → Sulfoxide → Sulfone. meta-Chloroperoxybenzoic acid. Concerted mechanism. Stereospecific.
Swern Oxidation Reagents
Swern Oxidation Reagents ((COCl)₂ + DMSO + Et₃N) - oxidizing reagent. Mild oxidation of alcohols to aldehydes/ketones. Common uses: 1° Alcohol → Aldehyde, 2° Alcohol → Ketone. No heavy metals. Very mild. Done at -78°C. Smelly byproduct (dimethyl sulfide).
Ozone
Ozone (O₃) - oxidizing reagent. Oxidative cleavage of alkenes. Common uses: Alkene → Aldehydes/Ketones (reductive workup: Zn or DMS), Alkene → Carboxylic acids/Ketones (oxidative workup: H₂O₂). Ozonolysis at -78°C, then workup. Useful for determining alkene s...
Sodium Hydroxide
Sodium Hydroxide (NaOH) - base reagent. Strong base, good nucleophile. Common uses: SN2 reactions (OH⁻ as nucleophile), E2 elimination, Ester/amide hydrolysis, Aldol condensation. Strong base and good nucleophile. pKa of water ~16.
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.
Potassium tert-Butoxide
Potassium tert-Butoxide (KOC(CH₃)₃) - base reagent. Strong, bulky base - favors elimination. Common uses: E2 elimination (Hofmann product), When steric hindrance wanted. Bulky base favors less substituted alkene (Hofmann). Poor nucleophile.
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...
Sodium Hydride
Sodium Hydride (NaH) - base reagent. Strong base (deprotonation), poor nucleophile. Common uses: Deprotonation of alcohols to alkoxides, Deprotonation of active methylene compounds, Williamson ether synthesis. Not a reducing agent in practice! Just a base. H₂...
Triethylamine
Triethylamine (Et₃N) - base reagent. Mild base, acid scavenger. Common uses: Neutralize HCl in acylations, Promote elimination, Swern oxidation. Mild base (pKa ~11). Good for neutralizing acid byproducts.
Pyridine
Pyridine (C₅H₅N) - base reagent. Mild base and nucleophilic catalyst. Common uses: Acylation reactions, Eliminate HCl in reactions with SOCl₂, TsCl. Aromatic amine. Weaker base than aliphatic amines. Bad smell.
DBU
DBU (C₉H₁₆N₂) - base reagent. Strong, non-nucleophilic organic base. Common uses: E2 elimination, Deprotonation reactions. 1,8-Diazabicyclo[5.4.0]undec-7-ene. Non-nucleophilic amidine base.
Sulfuric Acid
Sulfuric Acid (H₂SO₄) - acid reagent. Strong acid catalyst. Common uses: Fischer esterification, Alcohol dehydration, Nitration (with HNO₃), Sulfonation. Strong acid and dehydrating agent. Use catalytically.
Hydrobromic Acid
Hydrobromic Acid (HBr) - acid reagent. Acid for hydrohalogenation. Common uses: Alkene + HBr → Alkyl bromide (Markovnikov), Alcohol → Alkyl bromide (with heat). Markovnikov addition to alkenes. SN1 with tertiary alcohols.
Hydrochloric Acid
Hydrochloric Acid (HCl) - acid reagent. Strong acid for protonation and hydrohalogenation. Common uses: Alkene + HCl → Alkyl chloride, Workup of organometallic reactions. Weaker acid than HBr, HI for hydrohalogenation.
Nitric Acid
Nitric Acid (HNO₃) - acid reagent. Nitrating agent (with H₂SO₄). Common uses: Nitration of aromatics (with H₂SO₄). H₂SO₄ protonates HNO₃ to form NO₂⁺ (nitronium ion).
Aluminum Chloride
Aluminum Chloride (AlCl₃) - catalyst reagent. Lewis acid catalyst. Common uses: Friedel-Crafts alkylation, Friedel-Crafts acylation. Activates alkyl halides and acyl halides by making R⁺ or RCO⁺.
Iron(III) Bromide
Iron(III) Bromide (FeBr₃) - catalyst reagent. Lewis acid catalyst for halogenation. Common uses: Bromination of benzene. Made in situ from Fe + Br₂. Activates Br₂ for EAS.
Boron Trifluoride
Boron Trifluoride (BF₃ (as BF₃·Et₂O)) - catalyst reagent. Lewis acid. Common uses: Epoxide ring opening, Friedel-Crafts reactions, Aldol reactions. Strong Lewis acid. Often used as etherate (BF₃·OEt₂).
Sodium Azide
Sodium Azide (NaN₃) - nucleophile reagent. Nucleophile for SN2, not basic. Common uses: SN2 to make alkyl azides, Azide reduced to amine (LiAlH₄ or H₂/Pd). Good nucleophile, weak base → favors substitution over elimination.
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.
Tosyl Chloride
Tosyl Chloride (TsCl (p-CH₃C₆H₄SO₂Cl)) - leaving groups reagent. Converts OH to good leaving group (OTs). Common uses: Alcohol → Tosylate (ROH → ROTs), Tosylate undergoes SN2 with inversion. OTs is excellent leaving group, similar to Br⁻. Use pyridine as base.
Mesyl Chloride
Mesyl Chloride (MsCl (CH₃SO₂Cl)) - leaving groups reagent. Converts OH to good leaving group (OMs). Common uses: Alcohol → Mesylate, Mesylate undergoes SN2. Similar to TsCl but smaller. OMs is good leaving group.
Grignard Reagent
Grignard Reagent (RMgBr (or RMgCl)) - nucleophile reagent. Carbon nucleophile for C-C bond formation. Common uses: Aldehyde + RMgBr → 2° alcohol, Ketone + RMgBr → 3° alcohol, Formaldehyde + RMgBr → 1° alcohol, CO₂ + RMgBr → Carboxylic acid, Epoxide + RMgBr →...
Organolithium
Organolithium (RLi (e.g., n-BuLi)) - nucleophile reagent. Strong base and carbon nucleophile. Common uses: Deprotonation (stronger than Grignard), Nucleophilic addition to carbonyls, Metal-halogen exchange. More reactive than Grignard. n-BuLi and t-BuLi most...
Gilman Reagent (Cuprate)
Gilman Reagent (Cuprate) (R₂CuLi) - nucleophile reagent. Conjugate addition and coupling. Common uses: 1,4-addition to enones (not 1,2), Coupling with alkyl halides. Softer nucleophile than Grignard/organolithium. Prefers conjugate addition.
Thionyl Chloride
Thionyl Chloride (SOCl₂) - other reagent. Converts alcohols and acids to chlorides. Common uses: Alcohol → Alkyl chloride (inversion), Carboxylic acid → Acyl chloride. Gaseous byproducts (SO₂, HCl) make workup easy. Use pyridine as base.
Phosphorus Tribromide
Phosphorus Tribromide (PBr₃) - other reagent. Converts alcohols to alkyl bromides. Common uses: Alcohol → Alkyl bromide (inversion). Works via SN2 mechanism → inversion of stereochemistry.
NBS (N-Bromosuccinimide)
NBS (N-Bromosuccinimide) (C₄H₄BrNO₂) - other reagent. Bromination at allylic/benzylic positions. Common uses: Allylic bromination (radical mechanism), Benzylic bromination, Addition to alkenes (with water → bromohydrin). Provides low concentration of Br₂ for...
Borane-THF
Borane-THF (BH₃·THF) - other reagent. Hydroboration reagent. Common uses: Hydroboration of alkenes (then H₂O₂/NaOH → anti-Markovnikov alcohol). Concerted syn addition. No carbocation → no rearrangement.
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.
Wittig Reagent (Phosphorus Ylide)
Wittig Reagent (Phosphorus Ylide) (Ph₃P=CR₂) - nucleophile reagent. Converts C=O to C=C. Common uses: Aldehyde/Ketone → Alkene. Made from Ph₃P + R-X, then strong base. Produces alkene + Ph₃P=O.
DCC (Dicyclohexylcarbodiimide)
DCC (Dicyclohexylcarbodiimide) (C₁₃H₂₂N₂) - other reagent. Coupling reagent for amide/ester formation. Common uses: Carboxylic acid + Amine → Amide (peptide synthesis), Carboxylic acid + Alcohol → Ester. Activates carboxylic acid. Alternative: EDC (water-solu...
DMAP (4-Dimethylaminopyridine)
DMAP (4-Dimethylaminopyridine) (C₇H₁₀N₂) - catalyst reagent. Nucleophilic catalyst for acylations. Common uses: Speeds up esterification, Catalyst for acylations of hindered alcohols, Works with DCC/EDC couplings. Super-nucleophilic pyridine. Catalytic amount...
PDC (Pyridinium Dichromate)
PDC (Pyridinium Dichromate) (C₁₀H₁₂Cr₂N₂O₇) - oxidizing reagent. Mild oxidation of alcohols. Common uses: 1° Alcohol → Aldehyde, 2° Alcohol → Ketone, Allylic alcohols → α,β-unsaturated carbonyls. Similar to PCC but less acidic. Good for acid-sensitive substra...
Dess-Martin Periodinane (DMP)
Dess-Martin Periodinane (DMP) (C₁₃H₁₃IO₈) - oxidizing reagent. Very mild oxidation of alcohols. Common uses: 1° Alcohol → Aldehyde, 2° Alcohol → Ketone. Extremely mild, works at RT. Tolerates many functional groups. Expensive.
IBX (2-Iodoxybenzoic Acid)
IBX (2-Iodoxybenzoic Acid) (C₇H₅IO₄) - oxidizing reagent. Oxidation of alcohols. Common uses: 1° Alcohol → Aldehyde, 2° Alcohol → Ketone, Precursor to Dess-Martin periodinane. Less soluble than DMP. Used in DMSO. Can be explosive if heated dry.
L-Selectride
L-Selectride (Li[sec-Bu₃BH]) - reducing reagent. Stereoselective reduction of ketones. Common uses: Ketone → Alcohol (stereoselective), Reduction from less hindered face. Bulky hydride source. Gives equatorial alcohol from cyclohexanones. K-Selectride is anal...
Red-Al (Sodium bis(2-methoxyethoxy)aluminum hydride)
Red-Al (Sodium bis(2-methoxyethoxy)aluminum hydride) (NaAlH₂(OCH₂CH₂OMe)₂) - reducing reagent. Strong reduction, handles various substrates. Common uses: Ester → Alcohol, Amide → Amine, Nitrile → Amine, Epoxide opening. Milder than LiAlH₄ but still powerful....
Sodium Cyanoborohydride
Sodium Cyanoborohydride (NaBH₃CN) - reducing reagent. Selective reduction of imines. Common uses: Reductive amination (imine → amine), Selective at pH 6-7. Does NOT reduce aldehydes/ketones at neutral pH. Perfect for reductive amination. Releases HCN - toxic!
Sodium Triacetoxyborohydride
Sodium Triacetoxyborohydride (NaBH(OAc)₃) - reducing reagent. Mild, selective reduction. Common uses: Reductive amination, Reduces iminium ions selectively. Safer than NaBH₃CN (no HCN). Very selective. Mild conditions.
Pd(PPh₃)₄ (Tetrakis)
Pd(PPh₃)₄ (Tetrakis) (Pd(PPh₃)₄) - catalyst reagent. Pd(0) catalyst for cross-coupling. Common uses: Suzuki coupling, Stille coupling, Sonogashira coupling, Heck reaction. Air-sensitive (yellow powder). Pre-formed Pd(0). Alternative: Pd(dba)₂ + ligand.
Pd₂(dba)₃
Pd₂(dba)₃ (Pd₂(dba)₃) - catalyst reagent. Pd(0) precursor for cross-coupling. Common uses: Suzuki, Stille, Sonogashira couplings, Buchwald-Hartwig amination, More stable than Pd(PPh₃)₄. dba = dibenzylideneacetone. Add phosphine ligand for activity.
Grubbs Catalyst
Grubbs Catalyst (Cl₂(PCy₃)₂Ru=CHPh) - catalyst reagent. Olefin metathesis catalyst. Common uses: Ring-closing metathesis (RCM), Cross-metathesis, Ring-opening metathesis polymerization (ROMP). Ru-based, air-stable. 1st gen and 2nd gen available. Nobel Prize 2...
TBHP (tert-Butyl Hydroperoxide)
TBHP (tert-Butyl Hydroperoxide) ((CH₃)₃COOH) - oxidizing reagent. Oxidant for epoxidation and other oxidations. Common uses: Sharpless asymmetric epoxidation (with Ti), Oxidation reactions. Anhydrous version needed for Sharpless epoxidation. Commercial soluti...
Diethyl Tartrate (DET)
Diethyl Tartrate (DET) (C₈H₁₄O₆) - catalyst reagent. Chiral ligand for asymmetric synthesis. Common uses: Sharpless asymmetric epoxidation, D-(-)-DET and L-(+)-DET control enantioselectivity. D-tartrate: "draws" from right. L-tartrate: "draws" from left (mnem...
Arylboronic Acids
Arylboronic Acids (ArB(OH)₂) - nucleophile reagent. Coupling partner for Suzuki reactions. Common uses: Suzuki-Miyaura cross-coupling, Chan-Lam coupling (with Cu). Air-stable, low toxicity. Many commercially available. Pinacol esters also used.
DEAD (Diethyl Azodicarboxylate)
DEAD (Diethyl Azodicarboxylate) (EtO₂CN=NCO₂Et) - other reagent. Activator for Mitsunobu reaction. Common uses: Mitsunobu reaction (with PPh₃), Converts alcohols to other functional groups with inversion. Shock-sensitive! DIAD (diisopropyl analog) is safer al...
Hydrazine
Hydrazine (N₂H₄) - nucleophile reagent. Reducing agent and nucleophile. Common uses: Wolff-Kishner reduction, Gabriel synthesis (releases amine), Reduces nitro to amino groups. Toxic and potentially explosive! Handle with care.
Hydroxylamine
Hydroxylamine (NH₂OH) - nucleophile reagent. Forms oximes from carbonyls. Common uses: Ketone → Oxime (for Beckmann rearrangement), Aldehyde → Oxime. Usually used as hydrochloride salt (NH₂OH·HCl).
Manganese Dioxide
Manganese Dioxide (MnO₂) - oxidizing reagent. Selective oxidation of allylic/benzylic alcohols. Common uses: Allylic alcohol → α,β-unsaturated aldehyde, Benzylic alcohol → Benzaldehyde. Very selective - only oxidizes activated alcohols. Gentle conditions.
Silver(I) Oxide
Silver(I) Oxide (Ag₂O) - oxidizing reagent. Mild oxidation and halide activation. Common uses: Aldehyde → Carboxylic acid (Tollens test reagent component), Hofmann elimination (activates quaternary ammonium). Mild oxidizing agent. Creates Ag⁺ as activating sp...
18-Crown-6
18-Crown-6 (C₁₂H₂₄O₆) - catalyst reagent. Phase transfer catalyst, cation complexation. Common uses: Solubilizes KF, KOH, K₂CO₃ in organic solvents, Makes "naked" anions more reactive. Binds K⁺ strongly (cavity size matches K⁺). 15-Crown-5 for Na⁺.
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