Organic Chemistry - Reaction Types

Dehydration Reactions

• Tertiary and Secondary alcohols undergo E1

  • Can have alkyl and halide shifts

• Methyl and primary alcohols undergo E2

  • POCl3 is always E2

• ALWAYS E2

• Tertiary and Secondary alcohols undergo SN1

• Methyl and primary alcohols undergo SN2

• Alkoxide formation for ether synthesis

• Always SN2

• Only work with methyl and primary alcohols

• Always SN2

• Only work with methyl and primary alcohols

• No stereochemical change

• Creates good LG

• SN1 if R is secondary or tertiary

• SN2 if R is primary

Epoxide Rule with opticality

• Optically inactive reactants product optically inactive products

• In an unsymmetrical epoxide, the nucleophile attacks the LESS substituted carbon

• In an unsymmetrical epoxide, the nucleophile attacks the MORE substituted carbon

• Follows Markovnikov’s Rule

• Always SN1

• Addition is Syn and Anti

• Follows Markovnikov’s Rule

• Always SN1

• Addition is Syn and Anti

• Creates an ring that is then opened by the second halogen

  • NO POSSIBLE CARBOCATION

• Addition is Anti ONLY

• Creates an ring that is then opened by water

  • NO POSSIBLE CARBOCATION

• Addition is Anti ONLY

• Creates an ring that is then opened by water

  • NO POSSIBLE CARBOCATION

• Addition is Anti ONLY

• Another way of adding X2/H2O

• Addition is Syn ONLY

• Anti-Markovnikov

• Addition is Syn ONLY

• Anti-Markovnikov

• Markovnikov

Tautomers

• Enols shift to form ketones for more stability

• Anti-Markovnikov

• Anti-Markovnikov

• Acetylide anion

• Reactions involving it:

  • Primary or methyl alkyl halide: SN2

  • Secondary or tertiary: E2

• Formation of an internal alkyne