Orgo Reactants, Solvents, & Purposes

Alkynes + ? = vinylic halides & dihalides

hydrogen halides, peroxides, or Cl2, Br2

Alkynes + Hydrogen halides/peroxides/Cl2 or Br2 = ?

vinylic halides, dihalides

Alkynes + ? = ketones

Hg2+ - catalyzed hydration or hydroboration-oxidation

Alkynes + Hg2+/ catalyzed hydration/ hydroboration-oxidation = ?

Ketones

Alkynes + ? = other alkynes

NaNH3, then alkyl halide

Alkynes + NaNH3, then alkyl halide = ?

other alkynes

Alkynes + hydroboration-oxidation of 1-alkynes = ?

Aldehydes

Alkynes + ? = aldehydes

hydroboration-oxidation of 1-alkynes

Alkynes + H2/poisoned catalyst = ?

cis alkenes (from internal alkynes)

Alkynes + ? = cis alkenes

H2/poisoned catalyst

Alkynes + Na in liquid NH3 = ?

trans alkenes

Alkynes + ? = trans alkenes

Na in liquid NH3

Alkynes + H2 catalyst = ?

alkanes

Alkynes + ? = alkanes

H2 catalyst

Alkenes + ? = vinylic halides, dihalides

hydrogen halides (peroxidess)/Cl2/Br2

Alkenes + hydrgen halides/peroxides/Cl2/Br2 = ?

vinylic halides, dihalides

Alkenes + ? = halohydrins

halogens and water

Alkenes + halogens and water = ?

halohydrins

Alkenes + ? = cyclopropanes

Simmons-Smith; dihalocarbenes

Alkenes + Simmons-Smith; dihalocarbens = ?

cyclopropanes

Alkenes + ? = aldehydes or ketones

ozonolysis then Me2S

Alkenes + ozonolysis then Me2S = ?

aldehydes or ketones

Alkenes + ? = carboxylic acids or ketones

ozonolysis then H2O2

Alkenes + ozonolysis then H2O2 = ?

carboxylic acids or ketones

Alkenes + ? = alcohols

oxymercuration-reduction or hydroboration-oxidation or hydration

Alkenes + oxymercuration-reduction or hydroboration-oxidation or hydration = ?

alcohols

Alkenes + ? = alkanes

H2 catalyst

Alkenes + H2 catalyst = ?

alkanes

Alcohols + ? = alkyl halides

hydrogen halides, SOCl2, Ph3, PBr2

Alcohols + hydrogen halides, SOCl2, Ph3, PBr2 = ?

alkyl halides

Alcohols + ? = alkoxides

Na or NaH

Alcohols + Na or NaH = ?

alkoxides

Alcohols + ? = alkenes

acid-catalyzed dehydration of secondary and tertiary alcohols

Alcohols + acid-catalyzed dehydration of secondary and tertiary alcohols = ?

alkenes

Alcohols + ? = aldehydes

PCC oxidation of primary alcohols

Alcohols + PCC oxidation of primary alchols = ?

aldehydes

Alcohols + ? = ketones

oxidation of secondary alcohols

Alcohols + oxidation of secondary alcohols = ?

ketones

Alcohols + ? = carboxylic acids

oxidation of primary alcohols

Alcohols + oxidation of primary alcohols = ?

carboxylic acids

Alcohols + ? = sulfonate esters

sulfonyl chloride, pyridine

Alcohols + sulfonyl chloride, pyridine = ?

sulfonate esters

Alkoxides

conjugate bases of alcohols

Mercaptides

conjugate bases of thiols

Hydride (H-)

very strong base; reacts with alcohols to irreversibly form alkoxides

Amphoteric substances

can gain or lose a proton

H2SO4 & H3PO4

strong acids that catalyze dehydration

What kind of alcohol can’t go through dehydration?

Primary

What kind of reaction is dehydration?

E1

Oxidation

aka reducing agent; gains oxygen, loses hydrogen

Reduction

aka Oxidizing agent; loses oxygen, gains hyroge