University:
York University
Course:
CHEM 2021 | Introductory Organic Chemistry II
Academic year:

2023
Views:

362

Pages:

3
Author:

Niklas

Diagram: Top Left: A resonance structure of a carbonyl group, showing the delocalization of the pi electrons between the carbon and oxygen atoms. Top Right: An energy level diagram with two orbitals labeled "HOMO (Nu)" and "LUMO (E*)". Arrows indicate transitions between the orbitals. Bottom Left: A reaction mechanism showing a nucleophile (Nu:) attacking the carbonyl carbon of a carbonyl compound, followed by proton transfer. Bottom Right: A similar reaction mechanism, but the nucleophile attacks a protonated carbonyl group. Additional Text: Top Right: "come From 2sp²" "come From 2p" Bottom Left: "Act as E (π*)" "Nu:" Bottom Right: "*Act as Nu:" "E*" "H+" Example 1: Reactants: Ph-CH2-CH3 (phenyl group with an ethyl side chain) CH3MgBr (methyl magnesium bromide) Reagents: THF (tetrahydrofuran) H3O+ (acidic workup) Product: Ph-CH2-CH2-CH3 (phenyl group with a propyl side chain) Example 2: Reactants: Ph-CH2-CH3 NaBH4 (sodium borohydride) Reagents: LiAlH4, THF (lithium aluminum hydride in tetrahydrofuran) H3O+ Product: Ph-CH2-CH2-OH (phenyl group with an alcohol group) Example 3: Reactants: Ph-CH2-CH3 Ph-Li (phenyl lithium) Intermediate: Ph-CH=CH2 (phenyl group with a double bond) Product: Ph-CH2-CH2-Ph (two phenyl groups connected by a chain) Example 4: Reactants: Ph-CH2-CH3 Ph-Li Intermediate: Ph-CH=CH-Ph (two phenyl groups connected by a double bond) Reagents: H+ (acidic workup) Product: Ph-CH2-CH(Ph)-Ph (two phenyl groups connected to a carbon with a third phenyl group) Example 1: Reactant: CH3-CHO (aldehyde) Label: *MOST REACTIVE Note: *Highest 8+ on C Example 2: Reactant: CH3-CO-CH3 (ketone) Label: *LEAST REACTIVE Example 3: Reactant: Benzaldehyde (benzene ring with a CHO group) Label: *RESONANCE Note: *inductive effect