Organic Chemistry Reactions

Br2→light

adds Br to the more substituted position on an alkane

Cl2→Light

adds Cl to an alkene

HBr→

Replaces Alkene with Br; no stereochem preference

HBr→ROOR

Replaces Alkene with Br; Anti-markovnikov

H2SO4→H2O

Replaces Alkene with OH; no stereochem preference

Br2→Ch2Cl2

Replaces Alkene with Br on both ends of Alkene.

Cl2→H2O

Replaces an alkene with an OH and a Cl on the ends of the alkene.

1. Hg(OBc)2,H2O→

2. NBH4

Replaces an alkene with an OH on the more substituted carbon

1. BH#, THF→

2. H2O2, NaOH

Replaces an alkene with an OH on the less substituted carbon

1. OsO4→

2. H2O2,NaOH

Replaces alkene with 2 OHs on the ends of the alkene

1.O3→2. (CH3)2S

Splits alkene into 2 ketones; forms 2 molecules

H2→Pt/Pd/Ni Catalyst

removes alkene

Trace Br2→Light (NBS)

Adds Br while maintaining alkene

ROH→H catalyst

Replaces alkene with OR group

1. X2,H2O

   →

2. NaH,H2O

Replaces alkene with 2 bonds extending from both sides of the former alkene to the same O atom.

mCPBA→Ch2Cl2

Replaces alkene with 2 bonds extending from both sides of the former alkene to the same O atom

NaNH2→

Replaces H with Na

1. NaNH2

   →

2. Ch3X

Replaces H with CH3

HgSO4,H2SO4→
H2O

Transforms alkyne to a ketone

1. Sia2BH

2. H2O2,HO

Replaces alkyne with an alkene with 1 Br on each end

Br2, CCl4→ 2 eq.

Replaces alkyne with an alkene with 2 Brs on each end

H-X→1 eq.

Break alkyne into alkane and adds X onto more substitituted end

H-X→ 2 eq.

Breaks alkyne into alkane and adds 2Xs onto more substituted carbon.

H2, Cat. →

turns alkyne into alkane

H2, Lindlar →

turns alkyne into alkene with Z configuration

Na, NH3(liq)→CH3OH

turn alkyne into alkene with E configurations