Organic Chemistry: Exam 2

Catalytic Hydrogenation - Stereoselectivity

Syn-Addition

Catalytic Hydrogenation - Reagents

H₂ - Top and Pd/C - Bottom

Catalytic Hydrogenation - Products

2 Hydrogens

Hydrohalogenation - Regioselectivity

Markovnikov

Hydrohalogenation - Stereoselectivity

Syn and Anti Addition

Hydrohalogenation - Reactants

HBr, HCl, HI

Hydrohalogenation - Products

1 Halogen and 1 Hydrogen

Halogenation - Regioselectivity

“Markovnikov-Like”

Halogenation - Stereoselectivity

Anti-Addition

Halogenation - Reactants

Br₂ Typically

Halogenation - Products

2 Halogens

Bromohydrin Formation - Regioselectivity

“Markovnikov-Like”

Bromohydrin Formation - Stereoselectivity

Anti-Addition

Bromohydrin Formation - Reactants

Br₂ or NBS - Top and R-OH - Bottom

Bromohydrin Formation - Products

Bromine and OR Group

Acid-Catalyzed Hydration - Regioselectivity

Markovnikov

Acid-Catalyzed Hydration - Stereoselectivity

Syn AND Anti Addition

Acid-Catalyzed Hydration - Reactants

H₂O - Top and H₂SO₄ - Bottom

Acid-Catalyzed Hydration - Products

1 Hydrogen and 1 OH Group

Hydroboration-Oxidation - Regioselectivity

Anti-Markovnikov

Hydroboration-Oxidation - Stereoselectivity

Syn-Addition

Hydroboration-Oxidation - Reactants

BH₃-THF - Top and H₂O₂/NaOH/H₂O

Hydroboration-Oxidation - Products

1 Hydrogen and 1 OH Group

Epoxidation - Stereoselectivity

Syn-Addition

Epoxidation - Reactants

mCPBA or RCO₃H

Epoxidation - Products

Formation of Epoxide Ring

Ozonolysis - Reactants

O₃ at -78°C - Top and Zn/H₂O

Ozonolysis - Products

Catalyzed breaking of double bonds as if molecular scissors cut double bonds in half and added an oxygen on both sides

Syn-Dihydroxylation - Stereoselectivity

Syn-Addition

Syn-Dihydroxylation - Reactants

OsO₄ - Top and NaHSO₃/H₂O

Syn-Dihydroxylation - Products

2 OH Groups

Catalytic Hydrogenation (Alkynes) - Reactants

H₂ - Top and Pd/C - Bottom

Catalytic Hydrogenation (Alkynes) - Products

Alkanes

Catalytic Hydrogenation (Alkynes) with Catalyst - Reactants

H₂ - Top and Lindlar’s - Bottom

Catalytic Hydrogenation (Alkynes) with Catalyst - Products

Cis Alkene

Dissolving Metal Reduction - Reactants

Na at -78°C - Top and NH_{3 (l)} - Bottom

Dissolving Metal Reduction - Products

Trans Alkene

Alkynes: Hydrohalogenation - Regioselectivity

Markovnikov (Unless with ROOR then Anti-Mark.)

Alkynes: Halogenation - Regioselectivity

Markovnikov-Like`

Alkynes: Hydroboration-Oxidation - Regioselectivity

Anti-Markovnikov

Alkynes: Hydroboration-Oxidation - Reagents

9BBN-THF - Top and H₂O₂/NaOH/H₂O - Bottom

Alkynes: Hydroboration-Oxidation - Products

Alkene and OH Group THEN Double Bonded Oxygen and Hydrogen

Hydration of Alkynes: Acid-Catalyzed Hydration - Regioselectivity

Markovnikov

Hydration of Alkynes: Acid-Catalyzed Hydration - Reagents

H₂O - Top and H₂SO₄ - Bottom

Hydration of Alkynes: Acid-Catalyzed Hydration - Products

Enol with OH and THEN Keto with Oxygen

Alkylation of Acetylide Ions - Reactants

NaNH₂ - Top and NH₃ - Bottom

Alkylation of Acetylide Ions - Products

Connects triple bond with carbon chain through ionic charge