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DAT Bootcamp Reaction Summary Sheet .pdf


Original filename: DAT Bootcamp - Reaction Summary Sheet.pdf
Author: wesley son

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DAT Organic Chemistry Reaction Summary Sheet
Alkene Reactions
Hydrohalogenation

Hydrohalogenation
(with Rearrangement)
Halogenation

Hydrobromination with
Peroxide
Hydration
Hydration (with
Rearrangement)
Bromination in H2O

OxymercurationDemurcuration
HydroborationOxidation
Syn-Hydroxylation

Syn-Hydroxylation

Anti-Hydroxylation

Addition of an Alcohol
Bromination in Alcohol

AlkoxymercurationDemurcuration
Epoxidation

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Catalytic Hydrogenation
Ozonolysis (Reducing
Conditions)
Ozonolysis (Oxidizing
Conditions)
Oxidative Cleavage

Alkyne Reactions
Catalytic
Hydrogenation
(Catalytic Reduction)
Reduction to CisAlkene
Reduction to TransAlkene
Hydrohalogenation
with HBr (Terminal
Alkyne)
Hydrohalogenation
with HBr (Internal
Alkyne)
Halogenation with Br2

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
SN2 Addition of an
Acetylide Ion to a
Ketone
SN2 Addition of an
Acetylide Ion to an
Epoxide

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Ozonolysis

Oxidative Cleavage

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Free Radical Halogenation Reactions
Free Radical Halogenation
using Bromine (more
selective)
Free Radical Halogenation
using Chlorine (less
selective)

Br

Br2
hv or Δ
Cl

Cl

Cl2

Cl

hv or Δ

Cl

Allylic/Benzylic Bromination

NBS
hv or Δ
or ROOR

Br

NBS
hv or Δ
or ROOR

Br
Br

Diels Alder Reactions
Diene Addition to a
Dienophile (Alkene)

hv or

Diene Addition to a
Dienophile (Alkyne)

hv or

Diene Addition to a cis
Dienophile

hv or
same

Diene Addition to a trans
Dienophile

hv or
enantiomers

Diene Addition to a
substituted Dienophile

H

O
hv or

H

endo
(Major)
O

O

H
H

H
H

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O

H

O
exo
(Minor)

H
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Grignard Reactions
Addition of a Grignard
Reagent to an Aldehyde

O

1.
H

Addition of a Grignard
Reagent to a Ketone

O

OH

MgX , Ether

2˚Alcohol

2. H3O+
1.

MgX , Ether

HO
3˚Alcohol

2. H3O+
Addition of a Grignard
Reagent to an Ester

O

1. 2 eq.
O

Addition of a Grignard
Reagent to an Acyl Chloride

MgX, Ether

HO

O

1. 2 eq.
Cl

MgX, Ether

HO

2. H3O+

Addition of a Grignard
Reagent to CO2

3˚Alcohol

O
MgX

1. CO2, Ether

OH

2. H3O+
Addition of a Grignard
Reagent to an Epoxide (adds
to the less subs. side)

Addition of a Grignard
Reagent to a Carboxylic Acid

3˚Alcohol

2. H3O+

O

1.

MgX , Ether

Carboxylic Acid

OH

2. H3O+

O

1.
OH

MgX , Ether

O
O

2. H3O+

MgX

Carboxylate
Addition of a Grignard
Reagent to an Amide

O

MgX , Ether

1.
NH2

O
NH MgX

2. H3O+

Deprotonated Amide
Addition of a Grignard
Reagent to a Nitrile

N

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1.

MgX , Ether

2. H3O+

O
Ketone

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Electrophilic Aromatic Substitution (EAS) Reactions
Friedel-Crafts Alkylation
(Rearrangement Possible)

Cl
AlCl3

Cl
AlCl3
Friedel-Crafts Acylation
(No Rearrangement
Possible)

O

O

Cl
AlCl3

Bromination

Br2

Br

FeBr3
Chlorination

Cl2

Cl

FeCl3
Nitration

HNO3

NO2

H2SO4
Sulfonation

Formylation

O
CO, HCl

H

AlCl3
EAS with an ortho/paradirecting group on Benzene

O/P

O/P

O/P
Substituent

Substituent

Substituent
EAS with a meta-directing
group on Benzene

M

M
Substituent
Substituent

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Friedel-Crafts
Alkylation/Acylation with a
meta-directing group or an
amine on Benzene

M

O
R Cl

or Cl

R

No Reaction

AlCl3
NH2/NRH/NR2

O
R Cl

or Cl

R

No Reaction

AlCl3

Benzene Side-Chain Reactions
Side-Chain Oxidation of
Benzene to form Benzoic Acid

R
or

R

or

1. KMnO4, -OH
2.

R

H3O+,

Heat

O
OH

or
Na2Cr2O7
H2SO4

Wolff-Kishner Reduction

O
H2NNH2 or N2H4, -OH, Heat

Clemmensen Reduction

*can also use H2/Pd, C to achieve full reduction of carbonyl (C=O)
O

Zn(Hg), HCl, Heat

NO2

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Zn(Hg), HCl, Heat

NH2

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Hydride Reduction Reactions
Reduction of an Aldehyde to
a 1˚Alcohol

O

1. NaBH4, EtOH
H

O

1. LiAlH4, EtOH
H

Reduction of a Ketone to a
2˚Alcohol

2. H3O+

O

2. H3O+
1. NaBH4, EtOH

OH
H

OH
H
OH

2. H3O+

O

1. LiAlH4, EtOH

OH

2. H3O+
Reduction of a Carboxylic
Acid to a 1˚Alcohol

O

1. LiAlH4, EtOH
OH 2. H3O+

Reduction of an Ester to a
1˚Alcohol

O

1. LiAlH4, EtOH
O

Reduction of an Ester to an
Aldehyde

O

H
OH

O

O
H

2. H2O

1. LiAlH4, EtOH
Cl

OH

H

1. DIBAL-H, -78°C
O

Reduction of an Acyl Chloride
to a 1˚Alcohol

2. H3O+

OH

2. H3O+

OH
H

Reduction of an Acyl Chloride
to an Aldehyde
Reduction of an Amide to an
Amine

O

1. LiAlH4, EtOH
NH2

NH2 2. H3O+
Hoffmann Rearrangement

O

1. Br2
NH2 2. NaOH

Reduction of a Nitrile to an
Amine

N

1. LiAlH4, EtOH
2. H3O+

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NH2

NH2

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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

OH

HX

X

OH

HX

X

OH

PBr3

H

H
OH

Conversion of a 1˚/2˚Alcohol to an alkyl
chloride via SN2

SOCl2
H Pyridine

Conversion of an Alcohol to a Tosylate Ester
(OTs)

OH

OH

Chromic Acid Oxidation of a 1o Alcohol to a
Carboxylic Acid

OH
H

Br

PBr3

OH

OH

Acid-catalyzed Dehydration of an Alcohol

Br

Cl
H
Cl

SOCl2
Pyridine

OTs

TsCl

H3O+

Na2Cr2O7
or
CrO3

Retention of Stereochemistry

Zaitsev’s Rule

O

H2SO4

OH

o

Chromic Acid Oxidation of a 2 Alcohol to a
Ketone

OH

Na2Cr2O7
or
CrO3

O

H2SO4
Chromic Acid Oxidation of an Aldehyde to a
Carboxylic Acid

Na2Cr2O7
or
CrO3

O
H
PCC or DMP Oxidation of a 1o Alcohol to an
Aldehyde

OH

H2SO4
PCC or DMP

O
OH
O

H

H

o

PCC or DMP Oxidation of a 2 Alcohol to a
Ketone

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OH

PCC or DMP

O

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