OCHEM exam 4

anti and syn

hydrohalogenation of alkene produces

anti and syn

hydration of alkene produces

anti

halohydrin of alkene produces

syn

Hydroboration/oxidation of alkene produces

syn

hydrogenation of alkene with a metal produces

Z

The highest priority ligands on on the same side of the alkene

E

The highest priority ligands on the alkene are on opposite sides

Primary carbocations

Not stable and high in energy

Markovnikov’s rule

Hydrogen adds to the carbon with the most hydrogens, halogen adds to the carbon with the least hydrogens.

Anti-Markovnikov

When a halogen is mixed with hydrogen peroxide

Hydroboration-oxidation

Which reaction follows anti-markovnikov rule?

H2SO4 or HgSO4

What other reagent is needed in Hydration of Alkyne?

Keto group

Hydroboration-oxidation of Alkyne tautomerizes an OH to

Use strong base

How to make Acetylide from acetylene?

The one with the most H

Which carbon do Acetylides attack?

Enols

Tautomerize to Keto group

NaBH4

Replaces mercury with H

Mercury

Forms bridge on Alkene for water to attack more substituted carbon

Lindlar’s catalyst

Alkynes to Alkenes Syn addition

Na/NH3

Trans Addition Alkyne to Alkene

LiAlH4 To Alkyl Halides

SN2 X to H

LiAlH4 to Epoxides

Attack less substituted carbon with H, Water adds H to negative Oxygen

R-CO3H or MCPBH

Forms epoxides on Alkenes

H2O after MCPBH

Forms Anti -OH additions on alkene

Os and HSO3

Forms Syn OH groups on alkene

O3

Cuts Alkene or Alkyne adds O

O3 and Zn on Alkyne

adds O and H (aldyhyde)

O3 on alkyne

Adds O and OH (carboxylic acid)

Forms aldehyde

Primary alcohol with PCC or HCrO4

Forms Carboxylic acid

primary alcohol with CrO3+H2O+H2SO4

Forms ketones

Secondary alcohol with PCC or HCrO4

Diene

Two alkenes

Most stable diene

1 alkane between the two alkenes, (conjugated)