Organic CHM Reagents

Br₂ + FeBr₃

Aromatic bromination (Electrophilic Aromatic Substitution). Adds Br to a benzene ring.

Cl₂ + FeCl₃

Aromatic chlorination (Electrophilic Aromatic Substitution). Adds Cl to a benzene ring.

HNO₃ + H₂SO₄

Nitration. Adds NO₂ to a benzene ring via the nitronium ion (NO₂⁺).

SO₃ + H₂SO₄

Sulfonation. Adds SO₃H to a benzene ring.

R–Cl + AlCl₃ (or FeCl₃)

Friedel–Crafts alkylation. Adds an alkyl group (R) to a benzene ring.

RCOCl + AlCl₃

Friedel–Crafts acylation. Adds an acyl group (COR) to a benzene ring.

H₂, Pd/C (or Pt or Ni)

Hydrogenation. Reduces C=C to C–C.

Br₂

Alkene halogenation. Forms a bromonium ion. ANTI addition of Br and Br.

Br₂ + H₂O

Halohydrin formation. Adds Br and OH. OH goes to the more substituted carbon.

HBr

Hydrohalogenation. Markovnikov addition of H and Br.

HBr + ROOR

Radical hydrohalogenation. Anti-Markovnikov addition (HBr ONLY).

H₂O + H₂SO₄

Acid-catalyzed hydration. Adds OH by Markovnikov addition.

BH₃·THF then H₂O₂/OH⁻

Hydroboration-oxidation. Syn addition. OH adds anti-Markovnikov.

NaBH₄

Mild reducing agent. Aldehydes and ketones → alcohols.

LiAlH₄ then H₂O

Strong reducing agent. Reduces aldehydes, ketones, esters, carboxylic acids, and more.

PCC

Mild oxidation. 1° alcohol → aldehyde. 2° alcohol → ketone.

KMnO₄

Strong oxidation.

Mg, dry ether

Forms a Grignard reagent (RMgX).

Grignard reagent + carbonyl then H₃O⁺

Forms a new C–C bond and produces an alcohol.

NaNH₂

Very strong base. Deprotonates a terminal alkyne to form an acetylide ion.

NaOH

Strong base. Deprotonation/basification.

HCl

Strong acid. Protonates amines to form water-soluble ammonium salts.

DCM (CH₂Cl₂)

Organic solvent. Bottom layer during extraction.

Diethyl ether (Et₂O)

Top layer during extraction. Required solvent for Grignard reagents.

Na₂SO₄ or MgSO₄

Drying agent. Removes water from the organic layer