Reactions + Reagents/Products (Alkene Nucleophiles)

Alkene Nucleophiles —> Acid Initiated

Electrons from double bond = Nucleophile —> attack acidic H from top/bottom = racemic

Negative Conjugate Base group attach to most substituted carbon

• Stabilizing due to hyperconjugation

Hydration

Reagents: H2SO4, H2O excess

Products: OH on most substituted carbon of once-alkene and H on least substituted carbon of once-alkene

Addition to ALKYNE

Reagent: H-X (excess) [X: Br, Cl, etc)

Product: Hydrogens Attach to one carbon of once-alkyne, 2 X atoms bonded to carbon of once alkyne

Hydration of Alkyne

Reagents: H2SO4, H2O

Products: RC=OMe

Carbocation Rearrangements —> Ring Expansion

Reagents: H-X [X:Cl, Br, I] strong acid

Product: Ring expanded one more side

Carbocation Rearrangement —> rearranged to form more substituted carbocation

Reagents: H2SO4, H2O

Products: Carbon ring containing alkene —> Alkene replaced with Me group on one carbon (shifted Me from different carbon ring “alkyl migration”) and Hydrogen the other; Migrated Alkyl replaced with OH group

Rearrangement for resonance stability

Reagents: H-I (Strong Acid)

Product: Alkene group —> H on least substituted carbon, H from neighboring beta carbon shifts onto other carbon forming cation on beta carbon which attracts -I

Alkene Nucleophiles Electrophile Inititated

result in ANTI addition (Added Electrophile and Nucleophile groups anti of each other)

• What was trans originally is ANTI

• what was cis originally is SYN

Electrophile attract electrons from double bond and donate lone pair to one of the carbons in double bond to form 3 member ring

Dihalogenation

Reagent: X2 [X: Cl, Br]

Product: Anti X with same orientation on each carbon

Halohydrin Formation

Reagents: Br2/I2/Cl2, H2O

Product: Anti X and OH groups

EPOXIDATION

reagent: 1. mCPBA, CH2Cl2 2. NaOH, H2O

Product: Anti OH groups

Iodolactones

Reagent: 1. I2, H2O

Products: see image

Alkene Nucleophiles —> Syn Addition

Added groups on same side

• What was trans originally is ANTI

• what was cis originally is SYN

Hydroboration-Oxidation

Reagents: 1. BH3, THF (solvent) 2. NaOH, H2O2, H2O

Product: Cis Groups of H and OH

Alkyne Hydroboration-Oxidation

Reagents: 1. BH3, THF 2. NaOH, H2O2, H2O

Product: Alkyne —> Aldehyde

Hydrogenation

Reagents: H2, EtOH, Pd/C or Pd/I

Product: Cis H atoms bonded to each carbon

Alkyne Hydrogenation

Reagents:

• H2, EtOH, Pd/C —> Goes all the way to Alkane

• H2, EtOH, Pd/C, Pb+2, Purine —> goes only to alkene

Dihydroxylation

Reagent: OsO4, NaHSO3, H2O

Products: Cis groups of OH

Ozonolysis

Reagent: 1. O3, CH2Cl2 2. Me2S

Product: 2 Ketones

Radicals

Unpaired electrons formed by homolyzing a weak bond with heat or light

STABILIZERS:

• Sterics (More steric hinderance around radical = more stable)

• Electronegativity (less Electronegative the atom = more stable)

• Hyperconjugation (the more substituted the atom = more stable)

• Resonance (more resonance it can participate in = more stable; sp2 electrons)

Radical Chain Reaction

Reagent: RO-OR or X2 (Cl,Br)

1. Initiation: Homolyze weak bond of reagent with light/heat to create radical

2. Propogation: React with alkene

3. Termination: remaining radicals form a bond to end the reaction