Solvents Updated

Dehydration (starting material)

alcohol

Dehydration (Solvent)

Acid (H3O)

Dehydration (Product)

Hofmann Alkene

Hydration of alkenes (starting material)

alkene

hydration of alkenes (solvent)

acid (h3o)

hydration of alkenes (product)

alcohol group at most substituted C

hydrohalogenation (starting material)

alkene

hydrohalogenation (solvent)

H-X

Hydrohalogenation (product)

addition of X group at more substituted C

halogenation (starting material)

alkene

halogenation (solvent)

X2

halogenation (product)

anti addition of 2 halogen groups

halohydrin (starting material)

alkene

halohydrin (solvent)

X2, H2O

halohydrin (product)

Anti addition, OH on the more substituted, Br on the least substituted

oxymercuration (starting material)

alkene

oxymercuration (solvent)

1.Hg(OAC)2, H2)

2. NaBH4

oxymercuration (product)

addition of an OH group on a more substituted C

Radical Hydrohalogenation (starting material)

alkene

radical hydrohalogenation (solvent)

H-X, EtooEt, heat

radical hydrohalogenation (product)

addition of halogen on the least substituted C

Alkoxymercuration (starting Material)

alkene

alkoxymercuration (solvent)

1. Hg(OAC)2, HOCH3

2. NaBH4

alkoxymercuration (product)

addition of OCH3 to more substituted C

hydroboration (starting material)

alkene

hydroboration (solvent)

1. BH3, THF

2. H2O2, NaOH

hydroboration (product)

addition of an alcohol group to the less substituted OH

dihydroxylation (starting materials)

alkene

dihydroxylation (solvent)

OsO4, H2O2

dihydroxylation (product)

syn addition of two alcohol groups

hydrogenation (starting products)

alkene

hydrogenation (solvent)

H2 + metal catalyst (Pt, Pd)

hydrogenation (product)

syn addition to the two hydrogen

Osonolysis (starting material)

alkene

osonolysis (solvent)

1. O3

2. (Ch3)2S or H2O2

osonolysis (product)

Oxygens get added to fragments after double bonds break, and if H2O2, OH groups get added as well. Also CO2

making acetylide ions (starting materials)

alkyne

making acetylide ions (solvent)

strong base (NaNH2)

making acetylide ions (product)

negatively charged terminal alkyne with a lone pair

synthesis of an alkyne: acetylide + alkyl halide (starting material)

acetylide ion

synthesis of an alkyne: acetylide + alkyl halide (solvent)

R-X

synthesis of an alkyne: acetylide + alkyl halide (product)

internal Alkyne

synthesis of an alkyne: double elimination (starting materials)

geminal or vicinal dihalide (alkane)

synthesis of an alkyne: double elimination (solvent)

NaNH2

synthesis of an alkyne: double elimination (product)

internal alkyne

hydration of alkyne: Mercury + Acid (starting material)

alkyne

hydration of alkyne: Mercury + Acid (solvent)

1. HgSO4 2.H2O 3.H+

hydration of alkyne: Mercury + Acid (product pt.1)

alkene with an alcohol group at the most substituted C, Hg at the less substituted C --> replaced by H (enol)

hydration of alkyne: Mercury + Acid (product pt.2)

tautomerization, enol --> keto (double bond on C breaks and turns to O, H moves)

hydration of alkene: boron + base (starting material)

alkyne

hydration of alkene: boron + base (solvent)

1. Sia2BH

2. H2O2, NaOH

Halogenation of alkynes (starting material)

alkyne

halogenation of alkynes (solvent)

X2

halogenation of alkynes (product 1eq)

alkene, anti or syn addition of 2 X groups

halogenation of alkynes (product 2 eq)

alkane, addition of 4 x groups

Hydrogenation of Alkynes (starting material)

alkyne

hydrogenation of alkynes: metal catalyst (solvent)

H2 + Pt, Pd, Ni

hydrogenation of alkynes: metal catalyst (product)

2 syn additions of hydrogen, alkane

hydrogenation of alkynes: "poisoned" metal catalyst (solvent)

1. H2, Pd/BaSO4

2. Quinoline (Lindlar's catalyst)

hydrogenation of alkynes: "poisoned" metal catalyst (product)

cis alkene, 2 syn additions

hydrogenation of alkynes: dissolved electrons (solvent)

Na/NH3

hydrogenation of alkynes: dissolved electrons (product)

trans alkene

ozonolysis of alkynes (starting material)

alkyne

ozonolysis of alkynes (solvent)

1. O3

2. H20

ozonolysis of alkynes (product)