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Acetal and Hemiacetal Formation (acidic conditions)

 

Addition to Carbonyl: general mechanism (acidic conditions)

 

Addition to Carbonyl: general mechanism (basic conditions)

 

Alcohol Dehydration

 

Aldol Condensation (basic conditions)

 

Amide Formation (via anhydride)

 

Amide Hydrolysis (acidic conditions)

 

Amide Hydrolysis (basic conditions)

 

Arrow Pushing: Bronsted-Lowry acid H–A

 

Arrow Pushing: Bronsted-Lowry acid H–A+

 

Arrow Pushing: carbonyl addition (acidic conditions)

 

Arrow Pushing: carbonyl addition (basic conditions)

 

Arrow Pushing: collapse of tetrahedral intermediate (acidic conditions)

 

Arrow Pushing: collapse of tetrahedral intermediate (basic conditions)

 

Arrow Pushing: form/break C–X sigma bond

 

Arrow Pushing: form/break C–X+ sigma bond

 

Arrow Pushing: nucleophiles/electrophiles

 

Arrow Pushing: nucleophilic substitution (Nu + R–L)

 

Arrow Pushing: nucleophilic substitution (Nu + R–L+)

 

Carbocation Rearrangement: 1,2-alkyl shift

 

Carbocation Rearrangement: 1,2-hydride shift

 

Claisen Ester Condensation

 

Conjugate Addition

 

Cyanohydrin Reaction

 

Diels-Alder Reaction: cyclopentadiene + ethene

 

Diels-Alder Reaction: cyclopentadiene + maleic anhydride

 

Diels-Alder Reaction: general mechanism

 

E1 Elimination

 

E1cb Elimination

 

E2 Elimination

 

Electron Configuration

 

Electrophilic Aromatic Substitution: Friedel-Crafts acylation

 

Electrophilic Aromatic Substitution: Friedel-Crafts alkylation

 

Electrophilic Aromatic Substitution: general mechanism

 

Electrophilic Aromatic Substitution: halogenation

 

Electrophilic Aromatic Substitution: nitration

 

Electrophilic Aromatic Substitution: sulfonation

 

Enolate Alkylation

 

Epoxidation (with peracid)

 

Epoxide Opening (acidic conditions)

 

Epoxide Opening (basic conditions)

 

Ester Hydrolysis (acidic conditions)

 

Ester Hydrolysis (basic conditions)

 

Esterification (via acid chloride)

 

Fischer Esterification

 

Functional Group Explorer

 

Grignard Reaction of Aldehydes/Ketones

 

Halogenation of Alkenes

 

Halohydrin Formation

 

Henderson-Hasselbalch Equation

 

Hybridization: sp

 

Hybridization: sp2

 

Hybridization: sp3

 

Hydration of Alkenes

 

Hydration of Aldehydes/Ketones (acidic conditions)

 

Hydration of Aldehydes/Ketones (basic conditions)

 

Hydroboration-Oxidation of Alkenes

 

Hydrohalogenation of Alkenes

 

Imine Formation

 

Intramolecular Hemiacetal Formation (acidic conditions)

 

Lewis Structure: bromoethane

 

Lewis Structure: ethanal

 

Lewis Structure: ethane

 

Lewis Structure: ethanimine

 

Lewis Structure: ethanitrile

 

Lewis Structure: ethanoate anion

 

Lewis Structure: ethanol

 

Lewis Structure: ethene

 

Lewis Structure: ethyne

 

Lewis Structure: ethenyl carbanion

 

Lewis Structure: ethyl carbocation

 

Lewis Structure: ethyl carbanion

 

Lewis Structure: methanol

 

Lewis Structure: methanol (protonated)

 

Lewis Structure: methylamine anion

 

Lewis Structure: methylammonium cation

 

Lewis Structure: methoxide anion

 

Lewis Structure: nitromethane

 

Lewis Structure: propynyl carbanion

 

LiAlH4 Reduction of Aldehydes/Ketones

 

Localized Molecular Orbital Explorer: ethane

 

Localized Molecular Orbital Explorer: ethene

 

Localized Molecular Orbital Explorer: ethyne

 

Michael Reaction

 

Molecular Orbitals: LCAO theory

 

Molecular Orbitals: C–C sigma bonds

 

Molecular Orbitals: C–H sigma bonds

 

Molecular Orbitals: pi bonds

 

NaBH4 Reduction of Aldehydes/Ketones

 

Nucleophilic Aromatic Substitution

 

Oxidation of Alcohols

 

Oxymercuration-Reduction

 

[2+2] Photoaddition

 

Proton Transfer: B + H–A

 

Proton Transfer: B + H–A

 

Proton Transfer: B + H–A+

 

Resonance: acylium ion

 

Resonance: alkoxyalkyl carbocation

 

Resonance: allyl carbanion

 

Resonance: allyl carbocation

 

Resonance: amide

 

Resonance: benzene

 

Resonance: carbonyl group

 

Resonance: carbonyl group (protonated)

 

Resonance: carboxylate anion

 

Resonance: enolate anion

 

Resonance: ethanitrile anion

 

Resonance: formate anion

 

Resonance: nitrile (protonated)

 

Resonance: 1,3-pentadienyl carbocation

 

Resonance: 1,3-pentadienyl carbanion

 

Resonance: propynyl carbanion

 

Resonance: ynolate anion

 

Resonance: ortho-xylene

 

[1,3] Sigmatropic Rearrangement: alkyl shift

 

[1,3] Sigmatropic Rearrangement: hydride shift

 

[3,3] Sigmatropic Rearrangement: Claisen rearrangement

 

[3,3] Sigmatropic Rearrangement: Cope rearrangement

 

Skeletal Structure: codeine

 

Skeletal Structure: cholesterol

 

Skeletal Structure: clovene

 

SN1 Reaction: general mechanism

 

SN1 Reaction: AcO + R3CCl

 

SN1 Reaction: tBuOH + HCl

 

SN2 Reaction: CH3Cl + OH

 

SN2 Reaction: 2-chlorobutane + OH

 

SN2 Reaction: general mechanism

 

SN2 Reaction: Williamson ether synthesis

 

SN2' Reaction

 

Substitution at Carbonyl: general mechanism (acidic conditions)

 

Substitution at Carbonyl: general mechanism (basic conditions)

 

Tautomerization of Ketones (acidic conditions)

 

Tautomerization of Ketones (basic conditions)

 

Transesterification (basic conditions)

 

Wittig Reaction

 

Copyright © 2007, Ghislain Deslongchamps