addition reactions

Halohydrins

X_2, H₂O (in excess)

Halogenation

X_2, Inert solvent

Hydrohalogenation

HX, inert solvent

Acid-Catalyzed Hydration (Alkenes)

H₂O, H₂SO₄/H₃O⁺

Oxymercuration-Reduction

1. Hg(OAc)₂ / H₂O / THF (solvent)

2. NaBH₄, NaOH

Hydroboration-Oxidation (Alkenes)

1. BH₃ / THF

2. H₂O₂, NaOH

Ozonolysis

1. O₃

2. (CH₃)₂S —> ketones/aldehydes

3. H₂O₂/H₂O —> ketones/carboxylic acids

Hydroboration-Oxidation (Alkynes)

1. R₂BH

2. H₂O₂, NaOH

Acid-Catalyzed Hydration (Alkynes)

H₂O, H₂SO₄, Hg²⁺

Catalytic Hydrogenation

1. H₂

2. Lindler’s Catalyst (Pd/C) —> cis-alkene

Which additions form ketones?

1. Ozonolysis (both reagents)

2. Hydroboration-Oxidation (internal alkyne)

3. Acid-Catalyzed Hydration

Which additions form aldehydes?

1. Ozonolysis (CH₃)₂S

2. Hydroboration-Oxidation (terminal alkyne)

Which additions have carbocation intermediates?

1. Hydrohalogenation (Addition of HX)

2. Acid-Catalyzed Hydrogenation (Addition of Water)

**Can have hydride (H) or methyl (CH₃) shifts

Which additions add H2O?

1. Oxymercuration-Reduction

2. Hydroboration-Oxidation

3. Acid-Catalyzed Hydration

4. Halohydrins

Which additions form alkyl halides?

1. Hydrohalogenation

2. Halogenation

**Occur over inert solvents

What is the difference between halogenation and hydrohalogenation?

Halogenation is the concerted addition of X₂; hydrohalogenation is the stepwise addition of HX

What is the difference between acid-catalyzed hydration and oxymercuration-reduction?

Acid-catalyzed hydration is the stepwise addition of H₂O; oxymercuration-reduction is the concerted addition of H₂O