Reagent Reaction Mechanisms

alkyl halide MeOH

uni

alkyl halide H2O

uni

alkyl halide NaOMe

E2

alkyl halide t-buOK

E2 (bulky)

alkyl halide KOEt

E2

alkyl halide NaBr

Sn2

alkyl halide

Sn2

alkyl halide NaOR

E2

alkyl halide NaNH2

E2

alkyl halide KCN

Sn2

alkyl halide ROH

uni

alkene 1)BH3,THF 2)H2O2,NaOH

substitution, anti-markov, syn, +OH +H

alkene 1) Hg(OAc)2, H2O 2)NaBH4,H2O

substitution, markov, anti, +OH +H

hydroboration-oxidation

1)BH3, THF 2)H2O2, NaOH

oxymercuration-demurcuration

1)Hg(OAc)2, H2O 2)NaBH4, H2O

hydrogenation

H2, catalyst

alkene H2, Pt

syn, +H +H

alkyl halide MeSH

uni

alkene HX

substitution, markov, nonstereo, +H +X

alkene H3O+

substitution, markov, nonstereo, +H +OH

conc. H2SO4

dehydration, -H -OH

dillute H2SO4

substitution, markov, nonstereo, +H +OH

HBr, ROOR

substitution, anti-markov, nonstereo +H +Br

X2

substitution, anti, +X +X

halogenation

X2

hydrohalogenation

HX

halohydrin formation

X2, H2O

alkene X2, H2O

substitution, OH markov, anti, +OH +X

alkene RCO3H, H3O+

substitution, anti, +OH +OH

alkene 1)OsO4, pyridine 2)NaHSO, H2O2

substitution, syn, +OH +OH

alkeme 1)KMnO4 2)H2O, OH-

substitution, syn, +OH +OH

alkene 1)MCPBA 2)H3O+

substitution, syn, +OH +OH

alkene OsO4 (catalytic) , t-buOOH

substitution, syn,+OH +OH

oxidative cleavage

1) O3 2)DMS

1) excess NaNH2 2)H2O

double elimination, geminal dihalide -X -H -X -H +H

NaNH2 (2 equivalents)

E2 E2, vicinal dihalide, -X -H -X -H

alkyne H2, Pt

+H +H +H +H

complete hydrogenation

H2, Pt

incomplete hydrogenation

H2, lindlar catalyst

alkyne H2, lindlar catalyst

cis, +H +H

alkyne 1)NaNH3(l) 2)H2O

trans, +H +H

alkyne HX

alkene alkane mixture, substitution, markov, anti, +H +X, +H +X +H +X

alkyne excess HX

substitution, markov, geminal dihalide

alkyne Na, NH3 (l)

trans, +H +H

alkyne HX, ROOR

substitution, anti-markov, E and Z, +H +X

alkyne H2SO4, H2O / HgSO4

substitution, markov, +OH +H, ketone

alkyne hydration

H2SSO4, H2O HgSO4

acid-catalyzed tautomerization

enol → ketone

alkyne 1)R2BH, THF 2)H2O2, NaOH

substitution, anti-markov, +OH +H, aldehyde

base-catalyzed tautomerization

enolate → aldehyde

alkyne excess X2

+X +X +X +X

alkyne X2 (1 equivalent)

anti major, syn minor, +X +X

alkyne 1) O3 2) H2O

+O +OH +O + OH

alkyne 1)NaNH2 2)RX

substitution, +R

alkyne 1)NaNH2 2)EtI

substiution, +Et