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DAT Organic Chemistry Reaction Summary Sheet
Typology: Cheat Sheet
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Hydrohalogenation
Hydrohalogenation
(with Rearrangement)
Halogenation
Hydrobromination
with Peroxide
Hydration
Hydration (with
Rearrangement)
Bromination in H 2 O
Oxymercuration-
Demurcuration
Hydroboration-
Oxidation
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 Br 2
Hydration of an
Internal Alkyne
Hydration of a
Terminal Alkyne
(Markovnikov)
Hydration of a
Terminal Alkyne
(Anti-Markovnikov)
SN 2 Addition of an
Acetylide Ion to an
Alkyl Halide
SN 2 Addition of an
Acetylide Ion to a
Ketone
SN 2 Addition of an
Acetylide Ion to an
Epoxide
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
Addition of a Grignard
Reagent to an Acyl Chloride
3˚Alcohol
Addition of a Grignard
Reagent to CO 2
Carboxylic Acid
Addition of a Grignard
Reagent to an Epoxide
(adds to the less subs. side
forming the less subs.
alcohol)
2˚Alcohol (less subs. alcohol)
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
MgX
MgX
MgX
MgX
MgX
MgX
MgX
Cl
MgX
Friedel-Crafts Alkylation
(Rearrangement Possible)
Friedel-Crafts Acylation
(No Rearrangement
Possible)
Bromination
Chlorination
Nitration
Sulfonation
Formylation
EAS with an ortho/para-
directing group on
Benzene
EAS with a meta-directing
group on Benzene
Cl
AlCl 3
Cl
AlCl 3
FeCl 3
Cl Cl 2
Substituent
Substituent
Substituent
Substituent
Substituent
Cl
AlCl 3
2
4
AlCl 3
CO, HCl
FeBr 3
Br Br 2
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
Reduction of an Acyl
Chloride to a 1˚Alcohol
Reduction of an Acyl
Chloride to an Aldehyde
Reduction of an Amide to an
Amine
Hoffmann Rearrangement
Reduction of a Nitrile to an
Amine
Cl
LiAlH[OC(CH 3
3
3
Cl
2
Conversion of a 2˚/3˚Alcohol to an alkyl
halide via SN 1
Conversion of a 1˚/2˚Alcohol to an alkyl
bromide via SN 2
Conversion of a 1˚/2˚Alcohol to an alkyl
chloride via SN 2
Conversion of an Alcohol to a Tosylate Ester
(OTs) Retention of Stereochemistry
Acid-catalyzed Dehydration of an Alcohol
Zaitsev’s Rule
Chromic Acid Oxidation of a 1
o Alcohol to a
Carboxylic Acid
Chromic Acid Oxidation of a 2
o Alcohol to a
Ketone
Chromic Acid Oxidation of an Aldehyde to a
Carboxylic Acid
PCC or DMP Oxidation of a 1
o Alcohol to an
Aldehyde
PCC or DMP Oxidation of a 2
o Alcohol to a
Ketone
PBr 3
Br
SOCl 2
Cl
Pyridine
PBr 3
Br
SOCl 2
Cl
Pyridine
Na 2 Cr 2 O 7
or
CrO 3
Na 2 Cr 2 O 7
or
CrO 3
Na 2 Cr 2 O 7
or
CrO 3
TsCl
OTs
PCC or DMP
PCC or DMP
Addition of a 1˚ Amine to an Aldehyde or
Ketone forming an Imine (Reversed by
)
Addition of a 2˚ Amine to an Aldehyde or
Ketone forming an Enamine (Reversed
by H 3 O
)
Double bond forms on more substituted end for Ketones
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)
C or H
C or H
C or H
C or H
C or H
C or H
PPh 3
or
HSR etc.
(CH 3 CH 2 CH 2 ) 2 CuLi
Self Aldol
Condensation
and Enone
Formation
Mixed Aldol
Condensation
and Enone
Formation
Self Claisen
Condensation
Mixed Claisen
Condensation
Dieckmann
Cyclization
(Intramolecular
Claisen
Condensation)
Acetoacetic
Ester Synthesis
Malonic Ester
Synthesis
, NaOH
, NaOH
3
, Δ
, Δ
, NaOH
, NaOH
Halogenation
What’s added: 2 Br atoms
Regioselectivity: N/A
Stereoselectivity : Anti
Intermediate: Bromonium ion
Rearrangement: Not possible
Mechanism:
Hydrobromination with Peroxide
What’s added: H× and Br×
Regioselectivity: Anti-Markovnikov
Stereoselectivity : N/A
Intermediate: Radical
Rearrangement: Not possible
Mechanism:
Hydration
What’s added: H
and OH
Regioselectivity: Markovnikov
Stereoselectivity : N/A
Intermediate: Carbocation
Rearrangement: Possible (methyl and hydride shifts)
Mechanism:
Bromination in H 2 O
What’s added: Br
and OH
Regioselectivity: Markovnikov
Stereoselectivity : Anti
Intermediate: Bromonium ion
Rearrangement: Not possible
Mechanism:
Oxymercuration-Demurcuration
What’s added: H
and OH
Regioselectivity: Markovnikov
Stereoselectivity : Anti
Intermediate: Mercurinium ion bridge
Rearrangement: Not possible
Mechanism: You do not need to know the mechanism for this reaction
Addition of an Alcohol
What’s added: H
and OR
Regioselectivity: Markovnikov
Stereoselectivity : N/A
Intermediate: Carbocation
Rearrangement: Possible
Mechanism:
Bromination in Alcohol
What’s added: Br
and OR
Regioselectivity: Markovnikov
Stereoselectivity : Anti
Intermediate: Bromonium ion
Rearrangement: Not possible
Mechanism:
Alkoxymercuration-Demurcuration
What’s added: H
and OCH 3
Regioselectivity: Markovnikov
Stereoselectivity : Anti
Intermediate: Mercurinium ion
Rearrangement: Not possible
Mechanism: You do not need to know the mechanism for this reaction
Epoxidation
What’s added: O
Regioselectivity: N/A
Stereoselectivity : Syn
Intermediate: N/A
Rearrangement: Not possible
Mechanism: You do not need to know the mechanism for this reaction
Do know that a commonly-used peroxy acid is m-CPBA:
Catalytic Hydrogenation
What’s added: 2 H atoms
Regioselectivity: N/A
Stereoselectivity : Syn
Intermediate: N/A
Rearrangement: Not possible
Mechanism: You do not need to know the mechanism for this reaction
Ozonolysis in Reducing Conditions
What’s added: 2 O atoms
Regioselectivity: N/A
Stereoselectivity : N/A
Intermediate: N/A
Rearrangement: N/A
Mechanism: You do not need to know the mechanism for this reaction
Do know that the C=C double bond gets “sawed” in half, and an O atom is placed on the end of each new piece.
Note: (CH 3 ) 2 S is often abbreviated “DMS” for dimethyl sulfide.
Catalytic Hydrogenation
What’s added: 4 H atoms
Regioselectivity: N/A
Stereoselectivity : Anti
Intermediate: N/A
Rearrangement: Not possible
Mechanism: You do not need to know the mechanism for this reaction
Reduction to Cis-Alkene
What’s added: 2 H atoms
Regioselectivity: N/A
Stereoselectivity : Syn
Intermediate: N/A
Rearrangement: Not possible
Mechanism: You do not need to know the mechanism for this reaction
Reduction to Trans-Alkene
What’s added: 2 H atoms
Regioselectivity: N/A
Stereoselectivity : N/A
Intermediate: N/A
Rearrangement: Not possible
Mechanism: You do not need to know the mechanism for this reaction
Hydrohalogenation with HBr (Terminal Alkyne)
What’s added: 1 H atom and 1 halogen atom (can be F, Br, I, or Cl) per equivalent of HX
Regioselectivity: Markovnikov
Stereoselectivity : N/A
Intermediate: Carbocation
Rearrangement: Possible
Mechanism: The halogen goes to the C with fewer H’s
Hydrohalogenation with HBr (Internal Alkyne)
What’s added: 1 H atom and 1 halogen atom (can be Cl or Br) per equivalent of HX
Regioselectivity: Markovnikov
Stereoselectivity : N/A
Intermediate: Carbocation
Rearrangement: Possible
Mechanism: Same as for terminal alkynes, but yields a mixture of two products because both intermediates are
equally stable
Halogenation with Br 2
What’s added: 2 halogen atoms (can be F, Br, I, or Cl)
Regioselectivity: N/A
Stereoselectivity : Anti
Intermediate: Bromonium ion
Rearrangement: Not possible
Mechanism:
Hydration of an Internal Alkyne
What’s added: 1 O atoms
Regioselectivity: N/A
Stereoselectivity : N/A
Intermediate: N/A
Rearrangement: Not possible
Mechanism: You do not need to know the mechanism for this reaction
Do know that this reaction produces enols, which then tautomerize to form ketones.
