Diels-Alder Reactions
Diene Addition to a
Dienophile (Alkene)
Diene Addition to a
Dienophile (Alkyne)
Diene Addition to a cis
Dienophile
Diene Addition to a trans
Dienophile
Diene Addition to a
substituted Dienophile
Grignard Reactions
Addition of a Grignard
Reagent to an Aldehyde
2˚Alcohol
Addition of a Grignard
Reagent to a Ketone
3˚Alcohol
Addition of a Grignard
Reagent to an Ester
3˚Alcohol
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Addition of a Grignard
Reagent to an Acyl Chloride
3˚Alcohol
Addition of a Grignard
Reagent to CO2
Carboxylic Acid
Addition of a Grignard
Reagent to an Epoxide (adds
to the less subs. side)
Addition of a Grignard
Reagent to a Carboxylic Acid
Carboxylate
Addition of a Grignard
Reagent to an Amide
Deprotonated Amide
Addition of a Grignard
Reagent to a Nitrile
Ketone
Electrophilic Aromatic Substitution (EAS) Reactions
Friedel-Crafts Alkylation
(Rearrangement Possible)
Friedel-Crafts Acylation
(No Rearrangement
Possible)
Bromination
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Chlorination
Nitration
Sulfonation
Formylation
EAS with an
ortho/para-directing
group on Benzene
EAS with a meta-directing
group on Benzene
Friedel-Crafts
Alkylation/Acylation with a
meta-directing group or
an amine on Benzene
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Benzene Side-Chain Reactions
Side-Chain Oxidation of
Benzene to form Benzoic
Acid
Wolff-Kishner Reduction
Clemmensen Reduction
*can also use H2/Pd, C
*can also use H2/Pd, C or Sn/HCl
Acetylation of Aniline using
Acetic Anhydride
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Diazonium Salt Reactions
Hydride Reduction Reactions
Reduction of an Aldehyde to
a 1˚Alcohol
Reduction of a Ketone to a
2˚Alcohol
Reduction of a Carboxylic
Acid to a 1˚Alcohol
Reduction of an Ester to a
1˚Alcohol
Reduction of an Ester to an
Aldehyde
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Reduction of an Acyl
Chloride to a 1˚Alcohol
Reduction of an Acyl
Chloride to an Aldehyde
Reduction of an Amide to an
Amine
Hofmann Rearrangement
Reduction of a Nitrile to an
Amine
Alcohol Reactions
Conversion of a 2˚/3˚Alcohol to an alkyl
halide via SN1
Conversion of a 1˚/2˚Alcohol to an alkyl
bromide via SN2
Conversion of a 1˚/2˚Alcohol to an alkyl
chloride via SN2
Conversion of an Alcohol to a Tosylate Ester
(OTs) Retention of Stereochemistry
Acid-catalyzed Dehydration of an Alcohol
Zaitsev’s Rule
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Chromic Acid Oxidation of a 1o Alcohol to a
Carboxylic Acid
Chromic Acid Oxidation of a 2o Alcohol to a
Ketone
Chromic Acid Oxidation of an Aldehyde to a
Carboxylic Acid
PCC or DMP Oxidation of a 1o Alcohol to an
Aldehyde
PCC or DMP Oxidation of a 2o Alcohol to a
Ketone
Oxidative Cleavage of a 1,2 Diol
Swern Oxidation
Ether and Epoxide Reactions
Williamson Ether Synthesis via SN2
Acid-catalyzed Cleavage of Ethers when
one side is 2˚/3˚ (Nucleophile attacks
more substituted side via SN1)
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Acid-catalyzed Cleavage of Ethers
when neither side is 2˚/3˚ (Nucleophile
attacks less substituted side via SN2)
Acid-catalyzed Ring Opening of Epoxides
(Nucleophile attacks more substituted
side)
Base-catalyzed Ring Opening of
Epoxides (Nucleophile attacks less
substituted side)
Aldehyde and Ketone Reactions
Nucleophilic Addition to an Aldehyde or
Ketone
Addition of water to an Aldehyde or
Ketone forming a Hydrate
Base-catalyzed addition of an Alcohol
to an Aldehyde or Ketone forming a
Hemi-acetal/Hemi-ketal
Acid-catalyzed addition of an Alcohol
to an Aldehyde or Ketone forming a
Acetal/Ketal (Protecting Group, reversed
by H3O+)
Acid-catalyzed addition of Ethylene
Glycol to an Aldehyde or Ketone forming
a Acetal/Ketal (Protecting Group,
reversed by H3O+)
Addition of a 1˚ Amine to an Aldehyde or
Ketone forming an Imine (Reversed by
H3O+)
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Addition of a 2˚ Amine to an Aldehyde or
Ketone forming an Enamine (Reversed
by H3O+)
Double bond forms on less substituted end for ketones
Addition of a Wittig Reagent to an
Aldehyde/Ketone
Michael Addition to an α, β Unsaturated
Ketone
Michael Addition to an α, β Unsaturated
Ketone with a Gilman Reagent
(Organocuprates)
Nitrile Reactions
Acid-catalyzed Hydrolysis of a Nitrile
SN2 formation of Nitriles using Cyanide
and Alkyl Halides
Cyanohydrin Formation using
Aldehydes/Ketones and Cyanide
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Carboxylic Acid Derivative Reactions
Alpha Addition/Substitution Reactions
Self Aldol
Condensation
and Enone
Formation
Mixed Aldol
Condensation
and Enone
Formation
Self Claisen
Condensation
Mixed Claisen
Condensation
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Dieckmann
Cyclization
(Intramolecular
Claisen
Condensation)
Acetoacetic
Ester Synthesis
Malonic Ester
Synthesis
Alpha
Halogenation
In Basic
Conditions
Alpha
Halogenation in
Acidic
Conditions
Haloform
Reaction
*A methyl group is required for this reaction
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