Organic Chemistry Reagents and Transformations

Flashcards for organic chemistry reagents and their transformations.

PCC

1° alcohol -> aldehyde; 2° alcohol -> ketone

CrO3 / H2SO4 (Jones)

1° alcohol -> carboxylic acid; 2° alcohol -> ketone

KMnO4, H3O+

1° alcohol or alkene -> carboxylic acid

Swern (DMSO, oxalyl chloride, Et3N)

1° alcohol -> aldehyde; 2° alcohol -> ketone

NaBH4

Aldehyde/ketone -> alcohol

LiAlH4

Aldehyde/ketone/ester/acid/amide -> alcohol or amine

H2, Pd/C

Alkene/alkyne -> alkane

DIBAL-H, -78°C

Ester -> aldehyde

Na/NH3 (liq)

Alkyne -> trans-alkene

H2, Lindlar

Alkyne -> cis-alkene

Br2 or C12

Alkene/alkyne -> vicinal dihalide

1) BH3 THF 2) H2O2, OH-

Alkene -> anti-Markovnikov alcohol

1) Hg(OAc)2, H2O 2) NaBH4

Alkene -> Markovnikov alcohol

03 then H2O or Zn

Alkene -> carbonyls

TsCl, pyridine

Alcohol -> tosylate (good LG)

SOCI2

Alcohol -> alkyl chloride; acid -> acyl chloride

PBr3

Alcohol -> alkyl bromide

NaCN

Alkyl halide -> nitrile

NaN3

Alkyl halide -> azide (then -> amine)

NH3 or RNH2

Acyl chloride -> amide

ROH, H+

Carboxylic acid/acyl chloride -> ester

H2O

Acyl chloride -> acid

Heat, H3O+

Ester/nitrile -> carboxylic acid

Ph3P=CH2 (Wittig)

Aldehyde/ketone -> alkene

Grignard (RMgBr), then H3O+

Carbonyl -> alcohol with new C-C bond

NaNH2

Terminal alkyne -> acetylide ion

Heat, H2SO4

Alcohol -> alkene (E1)

NaOEt or KotBu

Alkyl halide -> alkene (E2)

Alkene → Alcohol

1. BH₃·THF, 2. H₂O₂, OH⁻ (anti-Markovnikov, syn)

Hg(OAc)₂, H₂O, NaBH₄ (Markovnikov)

Aldehyde/Ketone → Alcohol

NaBH₄, LiAlH₄

Carboxylic Acid → Alcohol

LiAlH₄, then H₃O⁺

Alcohol → Ketone/Aldehyde

PCC (stops at aldehyde), Jones (CrO₃, H₂SO₄) (to carboxylic acid if 1° alcohol)

Alcohol → Alkyl Halide

SOCl₂ (→ R–Cl), PBr₃ (→ R–Br), TsCl + Nu⁻

Alcohol Protection

TMSCl, imidazole (→ OTMS)

Deprotection

TBAF, H₃O⁺

Alcohol → Ether

NaH, then R–X (Williamson Ether)

Epoxide Opening (basic)

NaOEt, OH⁻, etc. (attacks less hindered C)

Epoxide Opening (acidic)

H⁺, ROH or H₂O (attacks more substituted C)

Nitration

HNO₃, H₂SO₄

Sulfonation

SO₃, H₂SO₄

Halogenation

Br₂/FeBr₃, Cl₂/AlCl₃

Friedel–Crafts Alkylation

R–Cl, AlCl₃

Friedel–Crafts Acylation

RCOCl, AlCl₃

NAS

LG (Cl) + EWG ortho/para + NaOEt

Diels–Alder

Diene + dienophile (with EWG), forms 6-membered ring, endo preferred

Aldehyde/Ketone

ROH + H⁺

Aldehyde/Ketone

RNH₂ + H⁺

Aldehyde/Ketone

R₂NH + H⁺

Aldehyde/Ketone

R–MgBr or R–Li

Aldehyde/Ketone → Alcohol

NaBH₄, LiAlH₄

Alcohol → Aldehyde/Ketone

PCC, DMP, Swern

COOH → Acid Chloride

SOCl₂

Acid Chloride → Ester

ROH, pyridine

Acid Chloride → Amide

NH₃, RNH₂

COOH → Ester

ROH, H⁺ (Fischer esterification)

Ester → COOH

H₃O⁺, heat or OH⁻, heat

Ester → Aldehyde

DIBAL-H, –78 °C

COOH → 1° Alcohol

LiAlH₄

Nitrile → Amine

LiAlH₄

Nitrile → Aldehyde

DIBAL-H, –78 °C