CHEM 232 Reagents Exam 4

Hydrogenation (Reagents / Addition / End Product)

H2, Pd/C or Pt / SYN / alkane

Alkene Hydrohalogenation (Reagents / Regiochem / Intermediate / adds…)

HX / Markovnikov / C+ / X

Alkene Hydration (Reagents / Regiochem / Intermediate / adds…)

H2SO4 / Markovnikov / C+ / OH

Alkene Isomerization (Reagents / regiochem)

H2SO4 / Markovnikov

Alkene Halogenation (Reagents / addition / adds…)

X2 / ANTI / X

Halohydrin synthesis (Reagents / addition / adds…)

X2 / ANTI / OH

Oxymercuration-Reduction (Reagents, regiochem, avoids…, adds…)

1. Hg(OAc)2, HOH/HOR 2. NaBH4, NaOH / Markovnikov / C+ / OH or OR

Hydroboration Oxidation (Reagents, addition, regiochem, avoids…, adds…)

1. BH3 2. H2O2, NaOH / SYN / anti-Markovnikov / C+ / OH

Epoxidation (Reagents, addition)

pereoxycarboxylic acid (mcPBA) / SYN

Syn-dihydroxylation (Reagents, addition)

OsO4 w/ amine oxide (TMAO) / SYN

Ozonolysis (Types, reagents, intermediate)

Reductive or oxidative / 1. O3 2. S(CH3)2 or 1. O3 2. H2O2, H2O / molozonide

SN2 w/ Alkyl Halides (Reagents / mechanism)

acetylide, electrophile / SN2

Reduction via Catalytic Hydrogenation (Reagents, addition, end product)

H2, Pd/C, Pt / SYN / alkane

Partial Reduction: Hydrogenation w/ Lindlar’s Catalyst (Reagents, addition, end product)

H2, Pd/CaCO3, Pb(OAc)2, quinoline / SYN / cis alkene

Partial Reduction: Hydrogenation w/ Sodium Metal in Ammonia (Reagents, addition, end product)

Na radical, NH3 / ANTI / trans alkene

Alkyne Hydrohalogenation (Reagents / regiochem)

HX / Markovnikov

Alkyne Halogenation (Reagents / additon)

X2 / anti

Hydration w/ Catalytic Hg2+ (Reagents, regiochem)

HgSO4, H2SO4, H2O / Markovnikov

Hydration w/ Hydroboration-Oxidation (Reagents / regiochem)

1. HB(bulky R) 2. H2O2, NaOH / Anti-Markovnikov