OCHEM Reagents list

H₂ / Pd, Pt, or Ni

Reduces alkenes/alkynes to alkanes;

Na / NH₃ (liq)

Reduces alkynes to trans-alkenes;

Lindlar catalyst Pd/CaCO3

Reduces alkynes to cis-alkenes;

mCPBA

Epoxidizes alkenes;

OsO₄ / H₂O₂

Syn dihydroxylation of alkenes;

KMnO₄ (cold, dilute)

Syn dihydroxylation of alkenes;

O₃ (ozonolysis)

Cleaves alkenes/alkynes to carbonyls;

BH₃ / THF, then H₂O₂, OH⁻

Anti-Markovnikov hydration of alkenes;

H₂SO₄, H₂O

Markovnikov hydration of alkenes;

Hg(OAc)₂, H₂O; NaBH₄

Oxymercuration; Markovnikov hydration w/o rearrangement;

HBr / ROOR

Anti-Markovnikov addition of HBr (radical conditions);

HX

Markovnikov addition of H and X;

Br₂

Anti-addition of Br₂;

Br₂ / H₂O

Halohydrin formation (OH on more substituted carbon);

H₂, Pd/C

Reduces aldehydes/ketones to alcohols;

NaBH₄

Reduces aldehydes/ketones to alcohols;

LiAlH₄

Reduces aldehydes, ketones, esters, acids to alcohols;

PCC

Oxidizes primary alcohols to aldehydes;

CrO₃ / H₂SO₄

Oxidizes primary alcohols to carboxylic acids; secondary to ketones;

Na₂Cr₂O₇ / H₂SO₄

Strong oxidation to carboxylic acids;

Jones reagent (CrO3)

)

Strong oxidation of primary/secondary alcohols;

SOCl₂

Converts alcohols to alkyl chlorides;

PX₃

Converts alcohols to alkyl halides;

TsCl / pyridine

Converts OH to OTs leaving group;

PBr₃

Converts alcohols to alkyl bromides;

H₂SO₄ (conc)

Dehydration of alcohols to alkenes;

H₂O, H₂SO₄

Acid-catalyzed substitution of alcohols;

NaOEt

E2 base; eliminates and forms alkenes;

t-BuOK

Bulky base; favors Hofmann elimination;

NaCN

SN2 nucleophile; installs nitrile;

NaN₃

SN2 nucleophile; installs azide;

NaOAc

SN2 nucleophile; installs acetate;

NaSH

SN2 nucleophile; installs thiol;

H₂N-R

SN2 nucleophile; installs amine;

Mg

Forms Grignard reagent;

RMgX

Strong nucleophile/base; attacks carbonyls;

CH₃Li or RLi

Very strong nucleophile/base;

H₂SO₄, HNO₃

Nitration of aromatics;

Br₂ / FeBr₃

Bromination of aromatics;

Cl₂ / FeCl₃

Chlorination of aromatics;

SO₃ / H₂SO₄

Sulfonation of aromatics;

AlCl₃, R-Cl

Friedel–Crafts alkylation;

AlCl₃, R-COCl

Friedel–Crafts acylation;

Zn(Hg), HCl

Clemmensen reduction; converts aldehyde or ketone into alkane

N₂H₄ / KOH

Wolff–Kishner reduction; converts aldehydes and ketones into alkanes

H₂, Pd/C (aromatic)

Hydrogenation of aromatic rings (forced conditions);