Organic Chemistry: Addition Reactions

hydrohalogenation (markovnikov edition)

reagents: HX

hydrohalogenation (anti-markovnikov edition)

reagents: HBr, ROOR

acid catalyzed hydration

regeants: H3O+

oxymercuration-demercuration

reagents:

1) Hg(OAc)2, H2O

2) NaBH4

hydroboration oxidation

reagents:

1) BHS * THF

2) H2O2, NaOH

catalytic hydrogenation

reagents: H2, metal catalyst

halogenation

reagents: X2 (X = Br or CL)

halohydrin formation

reagents: X2, H2O

anti-dihydroxylation

reagents:

1) RCO3H or MCPBA or peroxyacetic acid

2)H2O

syn-dihydroxylation

reagents:

1) KMnO4, NaOH (cold)

or

1) OsO4

2) NaHSO3, H2O

ozonolysis

reagents:

1) O3

2) DMS

ROOR/peroxides

what reagent will result in the anti-markovnikov edition of hydrohalogenation

hydrohalogenation

reagents: xs HX or (1 equivalent) HX

acid-catalyzed hydration

reagents:

1) H2SO4, H2O

2) HgSO4

hydroboration oxidation

reagents:

1) R2BH or 9-BBN or disiamylborane

2) H2O2, NaOH

poisoned catalytic hydrogenation

reagents: H2, Lindlar’s catalyst/Ni2B

dissolving metal reduction

reagents: Na, NH3 (l)

catalytic hydrogenation

reagents: H2, Pt/Pd/Ni

halogenation

reagents: X2 (1 equivalent) or xs X2, CCL4

ozonolysis

reagents:

1) O3

2) H2O

alkylation

reagents:

1) NaNH2

2) RX

ozonolysis

reagents:

1) O3

2) H2O

elimination

reagents:

1) xs NaNH2

2) H2O

H and X

what groups does hydrohalogenation add

H and Br

what groups does the anti-markovnikov version of hydrohalogenation add

H and OH

what groups does acid-catalyzed hydration add

H and OH

what groups does oxymercuration-demercuration add

H and OH

what groups does hydroboration oxidation add

H and H

what groups does catalytic hydrogenation add

X and X

what groups does halogenation add

X and OH

what groups does halohydrin formation add

OH and OH

what groups does anti-dihydroxylation add

OH and OH

what groups does syn-dihydroxylation add

O and O (carbonyl)

what groups does ozonolysis add

keto-enol tautomerization

what mechanism converts a ketone group into an enol