CHEM 333 - Reactions

SN1

- 2º or 3º
- weak/weak
- replace with nuc
-2 types of stereochem

SN2

- methyl, 1º, or 2º
- strong/strong
- strong/weak
- replace with nuc
- invert stereochem

E1

- 2º or 3º
- weak/weak
- add double bond on beta carbons

E2

- 1º, 2º, or 3º
- weak/strong
-strong/strong
- add double bond on beta carbons

HX addition to alkenes

- HI, HBR, HCl
- break double bond
- H on less, X on more
- both sides

Acid catalyzed Hydration of alkenes

- H2O, cat.H2SO4
- break double bond
- OH on more, H on less
- both sides

Br2/Cl2 Addition to alkenes

- Br2, Cl2
- break double bond
- opposite sides

Hydrobromination of Alkenes

- H2O, Br2
- break double bond
- OH on more, Br on less
- opposite sides

Metal Catalyzed Hydrogenation

- H2, Ni, Pd, Pt
- break double bond
- same side

Radical Halogenation of Alkenes

- Br2, light
- replace C-H bonds with C-Br bonds

Radical Addition to Alkenes

- HBr, ROOR, light
- break double bond
- H on more, Br on less
- both sides

Hydroboration / Oxidation

- BH3, NaOH, HOOH
- break double bond
- OH on less, H on more
- same side

Oxidation of Alcohols

- 1º or 2º OH
- replace C-H bonds with C-O bonds

SN1 Epoxide Reaction

- cat. H2SO4, H-nuc
- break O triangular ring
- nuc on more, OH on less
- both sides

SN2 Epoxide Reactions

- H3o+
- break O triangular ring
- replace with OH and nuc

Epoxides

- RO3H
- break double bond
- replace with O triangular ring

Hydrolysis of Ethers

- H2O, cat. H2SO4
- 2º or 3º
- break O bond
- add OH + new molecule

Acid Catalyzed Addition of Alcohols to Alkenes

- OH, cat.H2SO4
- break double bond
- OR on more, H on less
- same side

Acid Catalyzed Dehydration of Alcohols

- cat.H2SO4
- Replace OH with O
- add mirrored molecule

Dehydration of Alcohols

- cat. H2SO4, cat. TsOH
- break double bond
- OH on more

ROH to Tosylates

- TsCl, pyridine
- replace OH with OTs

PBr3 Reaction with ROH

- PBr3
- 1º or 2º
- replace OH with Br
- invert stereochem

E1 Elimination with H3PO4

- H3PO4
- replace beta carbons with double bonds

ROH reacts with HX to make R-X

- HBr, HI, HCl
- 2º or 3º
- replace OH with X

Oznolysis

- O3, Me2S
- break double bond
- fill with oxygen

dihydration

- OSO4, NaHSO3, H2O
- break double bond
- OH on both ends
- same side

Cyclopropanation

- CHCl3, NaOH
- break double bone
- add cuclochloro ring