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HBr

Halogen added Markovnikov across alkene

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HBr + ROOR (peroxides)

Halogen added Anti-Markovnikov across alkene

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H3O+, H2SO4, H2O

Alcohol added Markovnikov across alkene (possible shift)

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

Alcohol added Markovnikov across alkene (no shift)

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1) BH3, THF; 2) H2O2, NaOH

Alcohol added Anti-Markovnikov across alkene

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Br2

Two halogens added across alkene (anti-addition)

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Cl2, H2O

Halogen and OH added across alkene (anti-addition)

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H2, Pd/C

Alkene fully reduced to alkane

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H2, Lindlar's Catalyst

Alkyne reduced to cis-alkene

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Na/NH3

Alkyne reduced to trans-alkene

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H2SO4, H2O (acid workup)

Alkyne converted to ketone (Markovnikov hydration)

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1) BH3, THF; 2) H2O2, NaOH

• on alkynes: converted to aldehyde (Anti-Markovnikov hydration)

• on alkenes: converted to OH anti markovnikov

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Br2

Two halogens added across alkene (anti-addition)

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Cl2, H2O

Halogen and OH added across alkene (anti-addition)

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1) Br2; 2) NaNH2 (2 eq)

• alkane with two Brs (dihalide) —> alkyne

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NBS, hv

Radical bromination at allylic/benzylic position

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Br2, hv

Radical bromination at most substituted position

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SOCl2

OH —> Cl (no shift)

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PBr3

OH —> Br (no shift)

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HBr w OH

OH —> Br (possible shift)

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NaOMe

Halogen substituted with OMe

• OMe acts as nucleophile bc ionic bond

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NaBr / NaCl / NaX

Halogen substituted with another halogen

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NaNH2 or NaH

alkyne —> nucleophilic alkyne by removing H

• strong base

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NaH + aldehyde, then H2O

C-C bond formation with carbonyl group

• NaH depronates alkyne, making it a nucleophile

• aldehyde (carbonyl) is electrophile

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NaH + MeI

Methyl group added

• NaH depronates = wtv it depronates becomes nucleophile

• MeI would become an electrophile

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NaOH / NaOEt

alkane —> alkene (most substituted)

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KOtBu (bulky base)

alkane —> alkene (least substituted)

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