Organic Chemistry- Reactions Flashcards
Hydrohalogenation Alkene
HX, Treatment with an alkene gives a Markov Add of H and X
Hydrobromination Alkene
HBr, ROOR
Treatment of alkene gives anti Markov Add of H and Br
Acid Catalyzed Hydration Alkene
H3O+
Treatment of alkene gives Markov Add of H and OH. OH at more sub.
Oxymerc-demercuration Alkene
1)Hg(OAc)2, H2O
2) NaBH4
Treatment of alkene gives Markov Add of H and OH. No carbocation rearrange
Hydroboration Oxidation Alkene
1) BH3 THF
2) H2O2 NaOH
Treatment with alkene gives anti Markov add of H and OH. Syn addition + En
Hydrogenation Alkene
H2, Pt
Treatment of alkene gives syn add of H and H
Bromination Alkene
Br2
Treatment of alkene gives an anti addition of Br and Br. + En
Halohydrin formation Alkene
Br2, H20
Treatment of alkene gives anti add of Br and OH. OH at more subbed. + En
Anti Dihydroxylation Alkene
1)RCO3H 2) H3O+
Treatment of alkene converts it to an epoxide, which converts to a trans diol. + En
Syn Dihydroxylation #1 Alkene
KMnO4, NaOH, cold
With alkene gives a syn add of OH and OH. +En
Syn Dihydroxylation #2 Alkene
1) OsO4 2) NaHSO3, H2O
With alkene gives a syn add of OH and OH. + En
Ozonolysis Alkene
1) O3 2) DMS
With alkene cleaves C=C bond, giving two compounds each with C=O bond.
Which addition reactions give Markov products? Alkene
Hydrohalogenation, Acid Catalyze Hydration, and Oxymerc-demerc.
Which addition reactions give Anti-Markov products? Alkene
Hydrobromination and Hydroboration-oxidation
Which addition reactions give Syn addition products? Alkene
Hydrogenation and Syn Didroxylation
Which addition reactions give Anti addition products? Alkene
Bromination and Halohydrin formation
Which addition reaction gives Trans product? Alkene
Anti dihydroxylation
Elimination Alkyne
1) xs NaNH2
2) H20
A vicinal or geminal dibromide alkane is converted to an alkyne
Hydrohalogenation Alkyne
HX
Alkyne goes Markov addition x2 forming geminal dihalide.
Acid Catalyze Hydration Alkyne
H2SO4, H2O, HgSO4
Terminal alkyne undergoes Markov add of H and OH forming an enol, tautomerizes to ketone.
Hydroboration oxidation alkyne
1)R2BH 2) H2O2, NaOH
Terminal alkyne go anti Markov add of H and OH to enol, which tautomerizes to an aldehyde.
Halogenation Alkyne
X2, CCl4
Alkyne undergoes add of X and X (xs X2 gives tetrahalide).
Ozonolysis Alkyne
1)O3
2)H20
Alkyne is oxidatively cleaves C trip C bond. Internal alkynes are split into two carboxylic acids, while terminal alkynes are converted into a carboxylic acid and carbon dioxide.
Hydrogenation alkynes #1
H2, Lindlar’s Catalyst
Internal alkyne goes cis alkene
Hydrogenation alkynes #2
H2, Pt
Alkyne goes to alkane
Dissolving metal reduction
Na, NH3(l)
Internal alkyne is converted to trans alkene.
Alkylation
1) NaNH2
2) RX
Terminal alkyne goes to internal alkyne.
Radical bromination
Br2, hv
Alkane undergoes bromination where Br is installed at the most subbed.
Radical chlorination
Cl2, hv
Alkane is chlorinated. Less selective than bromination (but faster). Better for situations where one regiochemical outcome is possible.
Hydrobromination
HBr, ROOR
Alkene undergoes anti Markov add of H and Br
Allylic bromination
NBS, hv
Br installed at allylic position of an alkene
