All Orgo Reactions - Orgo Synthesis Reaction Cheat Sheet PDF

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Summary

Orgo Synthesis Reaction Cheat Sheet...

Description

Reaction Halogenation

Reactants

Product

Mark/Anti

Intermediate

Stereochem?

Rearrange?

None X on each side of bond

Bridged ion

Trans halides

No

Alkene X2 in apolar (CCl4, CH2Cl2)

Alkane

Dehydrohalogenation (E2)

Alkane

Alkene

Zaitsev unless bulky, then Hofmann

None

Anti-coplanar (β hydrogen and LG are 180˚ apart)

No

Double Dehydrohalogenation

Alkane

Alkyne

Mark

None

Unknown

No

Alkyne

Alkyne

Alkane

None

Bridged ion

Trans dihalides

No

Halogenation

X2 1 equiv.

Tetrahalide (2 vicinal)

2 X on each side of bond

Hydrohalogenation

Vicinal dihalides

Alkyl Halide w Base

Dihalide w Bulky Base

Alkene

Alkane

H—X

Alkyl Halide

Carbocation

None

Yes

Anti-mark addition of halide

Radical

None

Yes

Carbocation

None

No

Carbocation

None… but:

Yes

Alkane

Alkyne Alkyne Hydrohalogenation HX in excess

Alkane Geminal Dihalide

Mark addition of halide

Conjugated Diene Hydrohalogenation HX

Alkene

None

Halohydrin Formation

Alkene

Alkane

X2 in polar (H2O)

X & OH

Alkene

Alkane

Br2 in heat (Δ) or light

Allyl Bromide

Alkene

Alkane

Cl2 in heat (Δ) or light

Allyl Chloride

Allylic Bromination

Allylic Chlorination

X X

Mark addition of halide

Hydrohalogenation Alkene with peroxide HBr in ROOR

Alkyl Halide

X X

Allyl Br/Cl

>40˚=1,4 product...