DAT Bootcamp - Reaction Summary Sheet PDF

DAT Organic Chemistry Reaction Summary Sheet
Alkene Reactions
Hydrohalogenation
Hydrohalogenation
(with Rearrangement)
Halogenation
Hydrobromination
with Peroxide
Hydration
Hydration (with
Rearrangement)
Bromination in H2O
Oxymercuration-
Demurcuration
Hydroboration-
Oxidation
Syn-Hydroxylation
Syn-Hydroxylation
Anti-Hydroxylation
Addition of an Alcohol
Bromination in Alcohol
Alkoxymercuration-
Demurcuration
Epoxidation
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Catalytic
Hydrogenation
*Pt can also be used*
Ozonolysis (Reducing
Conditions)
Ozonolysis (Oxidizing 1. O3
2. H2O2
Conditions)/Oxidative O
Cleavage or O OH
1. KMnO4/heat
2. H3O+
Alkyne Reactions
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
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
Ozonolysis/Oxidative 1. O3
Cleavage on an 2. H2O2 O O
Internal Alkyne or OH HO
1. KMnO4/heat
2. H3O+
Ozonolysis/Oxidative 1. O3
Cleavage on a 2. H2O2 O
Terminal Alkyne CO2
or
OH
1. KMnO4/heat Terminal carbon becomes CO2
2. H3O+
Free Radical Halogenation Reactions
Free Radical Halogenation

Br
using Bromine (more Br2
selective) hv or Δ
Free Radical Halogenation

using Chlorine (less Cl
selective) Cl
Cl2
hv or Δ Cl
Cl
Allylic/Benzylic
Bromination NBS Br
hv or Δ
or ROOR
NBS Br
hv or Δ
or ROOR Br
Diels Alder Reactions
Diene Addition to a
hv or
Dienophile (Alkene)
Diene Addition to a
hv or
Dienophile (Alkyne)
Diene Addition to a cis

hv or
Dienophile
same
Diene Addition to a trans
hv or
Dienophile
enantiomers
Diene Addition to a H O
substituted Dienophile H
endo
(Major)
O H O
hv or H
H O
O
H
exo
(Minor)
H
H
Grignard Reactions
Addition of a Grignard O OH
1. MgX , Ether
Reagent to an Aldehyde
H 2. H3O+ 2˚Alcohol
Addition of a Grignard
O HO
Reagent to a Ketone 1. MgX , Ether
2. H3O+ 3˚Alcohol
Reagent to an Ester O 1. 2 eq. MgX, Ether HO
O 3˚Alcohol
2. H3O+
Reagent to an Acyl Chloride O 1. 2 eq. MgX, Ether HO
Cl 2. H3O+ 3˚Alcohol
O
Reagent to CO2
MgX 1. CO2, Ether
OH
2. H3O+ Carboxylic Acid
Addition of a Grignard OH
O 1. MgX , Ether
Reagent to an Epoxide
(adds to the less subs. side) 2. H3O+
Addition of a Grignard O O
1. MgX , Ether
Reagent to a Carboxylic Acid
OH O MgX
2. H3O+
Carboxylate
Addition of a Grignard O O
1. MgX , Ether
Reagent to an Amide
NH2 NH MgX
2. H3O+
Deprotonated Amide
Reagent to a Nitrile O
1. MgX , Ether
N Ketone
2. H3O+
Electrophilic Aromatic Substitution (EAS) Reactions
Friedel-Crafts Alkylation Cl
(Rearrangement Possible)
AlCl3
Cl
AlCl3
Friedel-Crafts Acylation O O
(No Rearrangement
Possible) Cl
AlCl3
Bromination
Br
Br2
FeBr3
Chlorination
Cl
Cl2
FeCl3
Nitration
NO2
HNO3
H2SO4
Sulfonation SO3H
SO3
H2SO4
H2SO4/Δ
Formylation
O
CO, HCl H
AlCl3
EAS with an ortho/para- O/P O/P O/P
directing group on Substituent
Substituent
Benzene
Substituent
EAS with a meta-directing M M
group on Benzene
Substituent
Substituent
Friedel-Crafts M O
Alkylation/Acylation with a
R Cl or Cl R
meta-directing group or No Reaction
an amine on Benzene AlCl3
NH2/NRH/NR2 O
R Cl or Cl R No Reaction
AlCl3
Benzene Side-Chain Reactions
Side-Chain Oxidation of R O
1. KMnO4, -OH
Benzene to form Benzoic
2. H3O+, Heat
Acid R R OH
or or or
Na2Cr2O7
H2SO4
1. KMnO4, -OH
2. H3O+, Heat
No Reaction (Requires free Hydrogen
or
at Benzylic position)
Na2Cr2O7
H2SO4
Wolff-Kishner Reduction O
H2NNH2 or N2H4, -OH, Heat
Clemmensen Reduction O
Zn(Hg), HCl, Heat
NO2 Zn(Hg), HCl, Heat NH2
*can also use H2/Pd, C in place of Zn(Hg), HCl, Heat for both reactions above
Acetylation of Aniline using
H
Acetic Anhydride NH2 O O N
O O
pyridine
Anilene Acetanilide
Hydride Reduction Reactions
Reduction of an Aldehyde to O 1. NaBH4, EtOH OH

a 1˚Alcohol
H 2. H3O+ H
O 1. LiAlH4, EtOH OH
H 2. H3O+ H
Reduction of a Ketone to a O 1. NaBH4, EtOH OH
2˚Alcohol
2. H3O+
O 1. LiAlH4, EtOH OH
2. H3O+
Reduction of a Carboxylic O OH
1. LiAlH4, EtOH
Acid to a 1˚Alcohol
OH 2. H3O+ H
Reduction of an Ester to a OH
O 1. LiAlH4, EtOH
1˚Alcohol
H OH
O 2. H3O+
Reduction of an Ester to an
Aldehyde O 1. DIBAL-H, -78°C O
O 2. H2O H
Reduction of an Acyl
O OH
Chloride to a 1˚Alcohol 1. LiAlH4, EtOH
Cl 2. H3O+ H
Reduction of an Acyl O
LiAlH[OC(CH3)3]3 O
Chloride to an Aldehyde
Cl H
Reduction of an Amide to an
O 1. LiAlH4, EtOH
Amine
NH2 2. H3O+ NH2
Hoffmann Rearrangement O
1. Br2
NH2 NH2
2. NaOH
Reduction of a Nitrile to an
1. LiAlH4, EtOH
Amine N NH2
2. H3O+
Alcohol Reactions
Conversion of a 2˚/3˚Alcohol to an alkyl OH X

HX
halide via SN1
OH HX X
Conversion of a 1˚/2˚Alcohol to an alkyl OH Br

PBr3
bromide via SN2
H H
OH PBr3 Br
Conversion of a 1˚/2˚Alcohol to an alkyl OH SOCl2 Cl

chloride via SN2
H Pyridine H
OH SOCl2 Cl
Pyridine
Conversion of an Alcohol to a Tosylate Ester

OH TsCl OTs
(OTs) Retention of Stereochemistry
Acid-catalyzed Dehydration of an Alcohol

OH
H3O+ Zaitsev’s Rule
Chromic Acid Oxidation of a 1o Alcohol to a

Carboxylic Acid Na2Cr2O7
or
OH CrO3 O
H H2SO4 OH
o
Chromic Acid Oxidation of a 2 Alcohol to a
Ketone Na2Cr2O7
or
OH CrO3 O
H2SO4
Chromic Acid Oxidation of an Aldehyde to a
Carboxylic Acid Na2Cr2O7
or
O CrO3 O
H H2SO4 OH
PCC or DMP Oxidation of a 1o Alcohol to an
OH O
Aldehyde PCC or DMP
H H
PCC or DMP Oxidation of a 2o Alcohol to a
OH PCC or DMP O
Ketone
Oxidative Cleavage of a 1,2 Diol HO OH O O

HIO4
H H
HO OH O O
HIO4
H
Ether and Epoxide Reactions
Williamson Ether Synthesis via SN2

NaH, Na, or K Cl
OH O O
Acid-catalyzed Cleavage of Ethers when

HBr
one side is 2˚/3˚ (Nucleophile attacks Br
O HO
more substituted side via SN1)
HBr
O Br HO
Acid-catalyzed Cleavage of Ethers

when neither side is 2˚/3˚ (Nucleophile O HBr OH
attacks less substituted side via SN2) Br
Acid-catalyzed Ring Opening of Epoxides

Cl
(Nucleophile attacks more substituted O HCl
OH
side)
OH
O H3O+
OH
Base-catalyzed Ring Opening of OH

Epoxides (Nucleophile attacks less O OCH3
O
substituted side) HOCH3
Aldehyde and Ketone Reactions
Nucleophilic Addition to an Aldehyde or O

Nucleophile HO Nucleophile
Ketone
C or H H3O+ C or H
Addition of water to an Aldehyde or O HO OH
Ketone forming a Hydrate H 2O
C or H C or H
H3O+ or -OH
Base-catalyzed addition of an Alcohol O HO O
O
to an Aldehyde or Ketone forming a
C or H C or H
Hemi-acetal/Hemi-ketal HO
Acid-catalyzed addition of an Alcohol O
H3O+ O O
to an Aldehyde or Ketone forming a
C or H C or H
Acetal/Ketal (Protecting Group, reversed HO
by H3O+)
H3O+
Acid-catalyzed addition of Ethylene OH
O HO O O
Glycol to an Aldehyde or Ketone forming
a Acetal/Ketal (Protecting Group, C or H C or H
H3O+
reversed by H3O+)
H3O+
Addition of a 1˚ Amine to an Aldehyde or O N

H 2N
Ketone forming an Imine (Reversed by
H3O+) C or H H3O+ C or H
H3O+
Addition of a 2˚ Amine to an Aldehyde or N

O N
Ketone forming an Enamine (Reversed H
by H3O+) C or H H3O+ C or H
H3O+
Double bond forms on more substituted end for Ketones

Addition of a Wittig Reagent to an
O PPh3
Aldehyde or Ketone
C or H C or H
Michael Addition to an α, β Unsaturated O O

Ketone O O
or -CN, HNR2,
HSR etc.
O
O
Michael Addition to an α, β Unsaturated
O O
Ketone with a Gilman Reagent (CH3CH2CH2)2CuLi
(Organocuprates)
Carboxylic Acid Derivative Reactions
Formation of an Acyl Chloride from a

Carboxylic Acid via SOCl2 O O
SOCl2
OH Cl
Fischer Esterification O O O
or H3O+/CH3CH2OH
OH Cl O
H3O+
Alpha Addition/Substitution Reactions
Self Aldol O O OH
-OH, H 2O H3O+, NaOH O
Condensation
2 H Δ
and Enone H H
Formation
O O O
-OH, H 2O OH H3O+, NaOH
2 Δ
Mixed Aldol O O O OH
-OH, H3O+, NaOH O
Condensation H 2O
H Δ
and Enone
Formation
O O
O O -OH, H 2O H3O+, NaOH
Δ
HO
Self Claisen
Condensation O O O
1. O
2 O O
2. H3O+
Mixed Claisen
Condensation O O O O
1. O
O 2. H3O+
Dieckmann
Cyclization O O O O
1. O
(Intramolecular O O O
Claisen 2. H3O+
Condensation)
Acetoacetic O O O
Ester Synthesis 1. O
O CO2 HO
2. Cl
3. O
4. Cl
5. H3O+, Δ
Malonic Ester O O O
Synthesis 1. O
O O HO CO2 2 HO
2. Cl
3. O
4. Cl
5. H3O+, Δ
DAT Organic Chemistry Reaction Details Sheet
Rearrangements Details
When carbocations form, H’s and CH3’s can do a 1,2-shift to generate a more stable carbocation intermediate
1,2-Hydride Shift
1,2-Methyl Shift
Alkene Reaction Details
Hydrohalogenation
What’s added: H+ and Br-

Regioselectivity: Markovnikov
Stereoselectivity: N/A
Intermediate: Carbocation
Rearrangement: Possible (methyl and hydride shifts)
Mechanism:
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
Intermediate: Radical
Mechanism:
Hydration
What’s added: H+ and OH-

Rearrangement: Possible (methyl and hydride shifts)
Mechanism:
Bromination in H2O
What’s added: Br+ and OH-

Mechanism:
Oxymercuration-Demercuration

Intermediate: Mercurinium ion bridge
Mechanism: You do not need to know the mechanism for this reaction
Hydroboration-Oxidation

Stereoselectivity: Syn
Intermediate: Hydroxy-boranes
Syn-Hydroxylation
or
What’s added: 2 OH groups

Intermediate: N/A
Mechanism:
Anti-Hydroxylation
What’s added: 2 OH groups

Intermediate: N/A
Mechanism: Epoxidation then reaction with aqueous acid or base.
In acidic conditions, the H2O attacks the more highly-substituted C:
In basic conditions, H2O attacks the less highly-substituted C:
Addition of an Alcohol
What’s added: H+ and OR-

Rearrangement: Possible
Mechanism:
Bromination in Alcohol
What’s added: Br+ and OR-

Mechanism:
Alkoxymercuration-Demercuration
What’s added: H+ and OCH3-

Intermediate: Mercurinium ion
Epoxidation
What’s added: O
Intermediate: N/A
Do know that a commonly-used peroxy acid is m-CPBA:
Catalytic Hydrogenation
What’s added: 2 H atoms

Intermediate: N/A
Note: You may see Pt used as well. This is just the catalyst and does not change the outcome of the products.
Ozonolysis in Reducing Conditions
What’s added: 2 O atoms

Intermediate: N/A
Rearrangement: N/A
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: (CH3)2S is often abbreviated “DMS” for dimethyl sulfide.
Ozonolysis in Oxidizing Conditions/Oxidative Cleavage
1. O3
2. H2O2 O
or O OH
1. KMnO4/heat
2. H3O+
What’s added: Multiple O atoms

Intermediate: N/A
Rearrangement: N/A
1. O3
2. H2O2 O
or O OH
1. KMnO4/heat
2. H3O+
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. Any
H’s attached to the alkene C’s get replaced by an –OH group since we are under oxidizing conditions/hot KMnO4.
Unlike reducing conditions which would have formed aldehydes, oxidizing conditions produces carboxylic acids
instead.
Alkyne Reaction Details
Catalytic Hydrogenation

Intermediate: N/A
Mechanism: You do not need to know the mechanism for this reaction.
Note: You may see Pt used as well. This is just the catalyst and does not change the outcome of the products.
Reduction to Cis-Alkene

Intermediate: N/A
Reduction to Trans-Alkene

Intermediate: N/A
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
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
Mechanism: Same as for terminal alkynes, but yields a mixture of two products because both intermediates are equally
stable
Halogenation with Br2
What’s added: 2 halogen atoms (can be F, Br, I, or Cl)

Mechanism:
Hydration of an Internal Alkyne
What’s added: 1 O atoms

Intermediate: N/A
Do know that this reaction produces enols, which then tautomerize to form ketones.
Hydration of a Terminal Alkyne (Markovnikov)
What’s added: 1 O atom

Intermediate: N/A
Do know that this reaction produces Markovnikov enols, which then tautomerize to form ketones.
Hydration of a Terminal Alkyne (Anti-Markovnikov)
What’s added: 1 O atom

Intermediate: N/A
Do know that this reaction produces Anti-Markovnikov enols, which then tautomerize to form aldehydes.
SN2 Addition of an Acetylide Ion to an Alkyl Halide
What’s added: additional C atoms (-R of alkyl halide)

Intermediate: Acetylide Ion
Mechanism: Deprotonation, then alkylation via SN2 reaction
SN2 Addition of an Acetylide Ion to a Ketone
What’s added: 2 additional alkyl groups and 1 –OH group

Mechanism: Deprotonation, then addition of a ketone via SN2 reaction
SN2 Addition of an Acetylide Ion to an Epoxide
What’s added: 2-hydroxylpropane (from epoxide)

Mechanism: Deprotonation, then addition of 2-hydroxyl propane via SN2 reaction
Ozonolysis/Oxidative Cleavage on an Internal Alkyne
1. O3
2. H2O2 O O
or OH HO
1. KMnO4/heat
2. H3O+
What’s added: 4 O atoms and 2 H atoms

Intermediate: Don’t worry about it! J
Mechanism: Don’t worry about it! J
Know that the reaction cuts a triple bond in half, very similar to ozonolysis on an alkene. An O replaces two of the
bonds as C=O and the third lone bond becomes a bond to -OH. Unlike ozonolysis, instead of forming the C-H bond
of an aldehyde, a C-OH bond of a carboxylic acid is formed.
1. O3
2. H2O2 O O
or OH HO
1. KMnO4/heat
2. H3O+
Ozonolysis/Oxidative Cleavage on a Terminal Alkyne
1. O3
2. H2O2 O
CO2
or
OH
2. H3O+
What’s added: 4 O atoms and 1 H atom

Intermediate: Don’t worry about it! J
Mechanism: Don’t worry about it! J
Know that the reaction cuts a triple bond in half, very similar to ozonolysis on an alkene. On the internal side, an O
replaces two of the bonds as C=O and the third lone bond becomes a bond to -OH. On the terminal side, two
oxygens O replaces all the bonds on carbon, forming the most oxidized form of carbon: CO2.
1. O3
2. H2O2 O
CO2
or
OH
2. H3O+
Free Radical Halogenation Reaction Details
Free Radical Halogenation using Bromine (more selective)
Br
Br2
hv or Δ
What’s added: 1 Br atom

Regioselectivity: Most Substituted Product
Intermediate: Radical Intermediate
Mechanism: Formation of bromine and carbon radicals and them joining to create an alkyl halide
1. Initiation
hv or Δ
Br Br Br Br
2. Propagation
H
Br
HBr
Br
Br Br Br
alkyl halide
3. Termination
Br Br Br Br
Free Radical Halogenation using Chlorine (less selective)
Cl
Cl2 Cl
hv or Δ Cl
Cl
What’s added: 1 Cl atom
Intermediate: Radical Intermediate
Mechanism: Formation of chlorine and carbon radicals and them joining to create alkyl halides
1. Initiation
hv or Δ
Cl Cl Cl Cl
2. Propagation
H
H
Cl Cl
HCl HCl
Cl
Cl
Cl Cl Cl Cl Cl Cl
alkyl halide
alkyl halide
Cl H Cl
HCl HCl
Cl Cl
Cl Cl
Cl Cl
alkyl halide Cl
Cl
alkyl halide
3. Termination
Cl Cl Cl Cl
Allylic/Benzylic Bromination
NBS Br
hv or Δ
or ROOR
NBS Br
hv or Δ
or ROOR Br
What’s added: 1 Br atom

Intermediate: Allylic Radical Intermediate
Note: this reaction results in the formation of allylic radical intermediates which resonate and thus allow for the
formation of multiple products.
Br Br
NBS
hv or Δ
or ROOR allylic radical intermediates
Br
Br
Grignard Reaction Details
Addition of a Grignard Reagent to an Aldehyde/Ketone
O OH
1. MgX , Ether
H 2º Alcohol
2. H3O+
O HO
1. MgX , Ether
2. H3O+ 3º Alcohol
What’s added: R group

Intermediate: Alkoxide ion
Rearrangement: N/A
Mechanism: Grignard reagents are electron-rich and attack electrophilic species such as carbonyls. The mechanism
follows typical nucleophilic addition to a carbonyl, forming 2º or 3º Alcohols.
O O
1. MgX , Ether
O
C or H 2. H3O+ C or H C or H
alkoxide intermediate
H3 O+ HO
C or H 2º or 3º Alcohol
Note: Using R-MgX is virtually the same reaction as using R-Li (organolithium); you are using the R-group as a
nucleophile to form an alcohol.
Addition of a Grignard Reagent to an Ester/Acyl Chloride
O 1. 2 eq. MgX, Ether HO

O 2. H3O+
O 1. 2 eq. MgX, Ether HO

Cl 2. H3 O+
What’s added: 2 R groups

Intermediate: Tetrahedral intermediate
Rearrangement: N/A
Mechanism: Grignard reagents are electron-rich and attack electrophilic species such as carbonyls. The mechanism
follows typical nucleophilic addition to a carbonyl with a twist; the Grignard reagent adds twice with esters and acyl
chlorides, forming 3º alcohols. Here it is shown on an ester (the same mechanism as with an acyl chloride):
O O
1. 2 eq. MgX, Ether O
O O O
2. H3O+
tetrahedral intermediate
O
O H3O+ HO
3º Alcohol
Carboxylic Acid Derivative Reaction Details
Fischer Esterification
O O O
or H3O+/CH3CH2OH
OH Cl O
H3O+
What’s added: An alcohol

Intermediate: Tetrahedral intermediate
Rearrangement: N/A
Mechanism: Essentially, this reaction substitutes the Cl or OH of an acyl chloride/ester with an alcohol:
O O OH OH
H3O+/CH3CH2OH H-OH2
HO
OH OH OH OH
H 2O
H
O O
HO O H3O+
HO O H
O O
OH OH2
tetrahedral intermediate
Notes: Notice that the reaction is reversible under H3O+/heat. The reverse reaction is how esters are cleaved into
their corresponding carboxylic acid and alcohol, an important biological process.

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DAT Organic Chemistry Reaction Summary Sheet

Free Radical Halogenation Reactions

Free Radical Halogenation

Free Radical Halogenation

Diels Alder Reactions

Diene Addition to a cis

Electrophilic Aromatic Substitution (EAS) Reactions

Benzene Side-Chain Reactions

NO2 Zn(Hg), HCl, Heat NH2

Hydride Reduction Reactions

Reduction of an Aldehyde to O 1. NaBH4, EtOH OH

Conversion of a 2˚/3˚Alcohol to an alkyl OH X

Conversion of a 1˚/2˚Alcohol to an alkyl OH Br

Conversion of a 1˚/2˚Alcohol to an alkyl OH SOCl2 Cl

Conversion of an Alcohol to a Tosylate Ester

Acid-catalyzed Dehydration of an Alcohol

Chromic Acid Oxidation of a 1o Alcohol to a

Oxidative Cleavage of a 1,2 Diol HO OH O O

Ether and Epoxide Reactions

Williamson Ether Synthesis via SN2

Acid-catalyzed Cleavage of Ethers when

Acid-catalyzed Cleavage of Ethers

Acid-catalyzed Ring Opening of Epoxides

Base-catalyzed Ring Opening of OH

Aldehyde and Ketone Reactions

Nucleophilic Addition to an Aldehyde or O

Addition of a 1˚ Amine to an Aldehyde or O N

Addition of a 2˚ Amine to an Aldehyde or N

Double bond forms on more substituted end for Ketones

Michael Addition to an α, β Unsaturated O O

Formation of an Acyl Chloride from a

Alpha Addition/Substitution Reactions

DAT Organic Chemistry Reaction Details Sheet

Alkene Reaction Details

What’s added: H+ and Br-

What’s added: 2 Br atoms

Hydrobromination with Peroxide

What’s added: H× and Br×

What’s added: H+ and OH-

What’s added: Br+ and OH-

What’s added: H+ and OH-

What’s added: H+ and OH-

What’s added: 2 OH groups

What’s added: 2 OH groups

In basic conditions, H2O attacks the less highly-substituted C:

What’s added: H+ and OR-

What’s added: Br+ and OR-

What’s added: H+ and OCH3-

What’s added: 2 H atoms

Ozonolysis in Reducing Conditions

What’s added: 2 O atoms

What’s added: Multiple O atoms

What’s added: 4 H atoms

What’s added: 2 H atoms

What’s added: 2 H atoms

Hydrohalogenation with HBr (Terminal Alkyne)

Halogenation with Br2

What’s added: 2 halogen atoms (can be F, Br, I, or Cl)

Hydration of an Internal Alkyne

What’s added: 1 O atoms

What’s added: 1 O atom

Hydration of a Terminal Alkyne (Anti-Markovnikov)

What’s added: 1 O atom