Organic Chemistry Reactions *Alkenes and Alkynes

Oxymercuration Demurcuration

• Markovnikov addition of OH

• No rearrangements

• Anti addition

Reagents:

Hg(OAc)2, H20, THF

NaBH4, OH-

Halogenation

• always anti addition

• No hydride or methyl shifts

Reagents:

X2/CCl4 (un reactive solvent, CHCl2 - with chlorine in it)

X2/H2O2

• X goes to less subsituted carbon

• Anti markovnikov addition

X2/H20 (reactive solvent)

• OH always ends up on the more substituted Carbon (H20 attacks more substituted carbocation)

• X on the less substituted Carbon

Hydrobormination with ROOR (H202)

• ANTI - Markovnikov addition

• No rearrangements

Where on an epoxide will be attacked?

If step one is a basic (negatively charged thing)

• then epoxide will be attacked at the LESS subsituted Carbon

• Easier to attack carbon

H2/Pd-C

Syn addition

• removes all double or triple bonds

Lindlar’s catalys

• removes only one bond

Na, NH3

• Anti addition

Hydroboration Oxidation

Forms anti - markovnikov product

Sodamide NaNH2 is used for?

• often used for forming alkynes for di-halides

What best describes the regioselectivity and stereoselectivity in the hydroboration-oxidation of an alkene?

Markovnikov vs not

Syn vs anti

Which best describes the regioselectivity and stereospecificity in the oxymercuration-demercuration of an alkene?