Organic Chemistry Flashcards
Addition of a gringnard reagent to CO2
Side-Chain Oxidation of
Benzene to form Benzoic
Acid
No Rxn (Requires free Hydrogen at
Benzylic position)
Hydrohalogenation
with HBr (Terminal
Alkyne)
Conversion of a 1°/2°Alcohol to an alkyl
bromide via SN2
Hydrohalogenation
with HBr (Internal
Alkyne)
Acetylation of Aniline using Acetic Anhydride
Formation of Aryl fluoride from a Diazonium salt
Alpha Halogenation in Basic Conditions
Formation of Aryl iodide from a Diazonium salt
Addition of a 1° Amine to an Aldehyde or
Ketone forming an Imine (Reversed by
H3O+)
Formation of Aryl cyanide (nitrile) from a Diazonium salt
Ester to Carboxylic Acid
Mixed Aldol
Condensation
and Enone
Formation Step 2:
Acid Anhydride to Amide
Diene Addition to a Dienophile (Alkene)
Formation of Phenol from a Diazonium salt
Acyl Chloride to Carboxylic Acid
Alkyne Formation from Double Elimination of a Vicinal Dihalide (step one)
Acid-catalyzed addition of Ethylene
Glycol to an Aldehyde or Ketone forming
a Acetal/Ketal (Protecting Group,
reversed by H3O+)
Carboxylic Acid to Acyl Chloride
Oxidative Cleavage of a asymmetric 1,2 Diol
Formation of Aryl chloride/bromide from a Diazonium salt
Amide to Carboxylic Acid
Amide to Carboxylate
Acid Anhydride to Carboxylate
Acyl Chloride to Ester
Addition of a 2° Amine to an Aldehyde or
Ketone forming an Enamine (Reversed
by H3O+)
Acyl Chloride to Carboxylate
Diene Addition to a Dienophile (Alkyne)
Alkyne Formation from Double Elimination of a Vicinal Dihalide (step two)
Diene Addition to a trans Dienophile
Reduction of a diazonium salt
Diene Addition to a cis Dienophile
Ozonolysis/Oxidative Cleavage on a Terminal Alkyne (Terminal carbon becomes carbon dioxide)
hydroboration - oxidation
(exo product)
Diene Addition to a substituted Dienophile
Ozonolysis/Oxidative Cleavage on an Internal Alkyne
Williamson Ether Synthesis via SN2 Step 2:
Ozonolysis/Oxidative Cleavage on an Internal Alkyne
SN2 formation of Nitriles using Cyanide and Alkyl Halides
Acid Anhydride to Ester
Acid-catalyzed addition of an Alcohol
to an Aldehyde or Ketone forming a
Acetal/Ketal (Protecting Group, reversed
by H3O+)
Acyl Chloride to Acid Anhydride reaction
Ester to Carboxylate
Haloform reaction (* A methyl group is required for this reaction)
Ester to Amide
Oxidative cleavage of a symmetric 1,2 Diol
Ozonolysis/Oxidative Cleavage on a Terminal Alkyne (Terminal carbon becomes carbon dioxide)
Acyl Chloride to Amide
Formation of Dazonium Salt from Aromatic Amine
Reduction of an Acyl Chloride to an Alhdehyde
Acid-catalyzed Hydrolysis of a Nitrile
swern oxidation
Cyanohydrin Formation using Aldehydes/Ketones and Cyanide
(endo product)
Diene Addition to a substituted Dienophile
Alpha Halogenation in Acidic Conditions
Hydration of an
Internal Alkyne
Hydration of a
Terminal Alkyne
(Markovnikov)
Hydration of a
Terminal Alkyne
(Anti-Markovnikov)
SN2 Addition of an
Acetylide Ion to an
Alkyl Halide Step 1:
SN2 Addition of an
Acetylide Ion to an
Alkyl Halide Step 2:
SN2 Addition of an
Acetylide Ion to a
Ketone Step 1:
SN2 Addition of an
Acetylide Ion to a
Ketone Step 2:
SN2 Addition of an
Acetylide Ion to an
Epoxide Step 1:
SN2 Addition of an
Acetylide Ion to an
Epoxide Step 2:
Free Radical Halogenation
using Bromine (more
selective)
Free Radical Halogenation
using Chlorine (less
selective)
Allylic/Benzylic
Bromination
Allylic/Benzylic
Bromination
Addition of a Grignard
Reagent to an Aldehyde
Addition of a Grignard
Reagent to a Ketone
Addition of a Grignard
Reagent to an Ester
Addition of a Grignard
Reagent to an Acyl Chloride
Addition of a Grignard
Reagent to an Epoxide
(adds to the less subs. side
forming the less subs.alcohol)
Addition of a Grignard
Reagent to a Carboxylic Acid
Addition of a Grignard
Reagent to an Amide
Addition of a Grignard
Reagent to a Nitrile
Friedel-Crafts Alkylation
(Rearrangement Possible)
Friedel-Crafts Alkylation
(Rearrangement Possible)
Friedel-Crafts Acylation
(No Rearrangement
Possible)
Bromination
Chlorination
Nitration
Sulfonation
Formylation
EAS with an ortho/paradirecting
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
No Rxn
Friedel-Crafts
Alkylation/Acylation with a
meta-directing group or
an amine on Benzene
No Rxn
Side-Chain Oxidation of
Benzene to form Benzoic
Acid
Wolff-Kishner Reduction
Clemmensen Reduction
Clemmensen Reduction
Reduction of an Aldehyde to
a 1°Alcohol
Reduction of an Aldehyde to
a 1°Alcohol
Reduction of a Ketone to a
2°Alcohol
Hydrohalogenation
Reduction of a Ketone to a
2°Alcohol
Hydrohalogenation
(with Rearrangement)
Halogenation
Hydrobromination
with Peroxide
Hydration
Hydration (with
Rearrangement)
Bromination in H2O
Oxymercuration-
Demurcuration
Syn-Hydroxylation
Syn-Hydroxylation
Anti-Hydroxylation
Addition of an Alcohol
Bromination in Alcohol
Alkoxymercuration-
Demurcuration
Epoxidation
Catalytic Hydrogenation
Ozonolysis (Reducing
Conditions)
Ozonolysis (Oxidizing Conditions)
Oxidative cleavage
Catalytic
Hydrogenation
(Catalytic Reduction)
Reduction to cis-alkene
Reduction to Trans-
Alkene
Hydrohalogenation
with HBr (Terminal
Alkyne)
Hydrohalogenation
with HBr (Internal
Alkyne)
Halogenation with Br2
Halogenation with Br2
Reduction of a Carboxylic
Acid to a 1°Alcohol
Reduction of an Ester to a
1°Alcohol
Reduction of an Ester to an
Aldehyde
Reduction of an Acyl
Chloride to a 1°Alcohol
Reduction of an Acyl
Chloride to an Aldehyde
Reduction of an Amide to an
Amine
Hoffman Rearrangement
Reduction of a Nitrile to an
Amine
Conversion of a 2°/3°Alcohol to an alkyl
halide via SN1
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 a 1°/2°Alcohol to an alkyl
chloride via SN2
Conversion of an Alcohol to a Tosylate Ester
(OTs)
Acid-catalyzed Dehydration of an Alcohol
Chromic Acid Oxidation of a 1degree Alcohol to a
Carboxylic Acid
Chromic Acid Oxidation of a 2 degree 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
Williamson Ether Synthesis via SN2 Step 1:
Acid-catalyzed Cleavage of Ethers when
one side is 2°/3° (Nucleophile attacks
more substituted side via SN1)
Acid-catalyzed Cleavage of Ethers when
one side is 2°/3° (Nucleophile attacks
more substituted side via SN1)
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)
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
Addition of a Wittig Reagent to an
Aldehyde or Ketone
Michael Addition to an α, β Unsaturated
Ketone
Michael Addition to an α, β Unsaturated
Ketone with a Gilman Reagent
(Organocuprates)
Self Aldol
Condensation
and Enone
Formation Step 1:
Self Aldol
Condensation
and Enone
Formation Step 2:
Mixed Aldol
Condensation
and Enone
Formation Step 1:
Mixed Aldol
Condensation
and Enone
Formation Step 2:
Mixed Aldol
Condensation
and Enone
Formation Step 1:
Self Claisen
Condensation
Mixed Claisen
Condensation
Dieckmann
Cyclization
(Intramolecular
Claisen
Condensation)
Acetoacetic
Ester Synthesis
Malonic Ester
Synthesis
Hydroboration oxydation (BH3/THF.. H2O2/H2O/OH) where does the OH go??
To the less substutited carbon.
Oxymurcuration demurcuration (HgAOc2, H2O/ NaBH4) where does the OH go??
To the more substuted carbon
