Alkene Reagents and Solvents

Dihalogenation

Reagent: Br₂ or Cl₂

Solvent: CCl₄

hydrohalogenation

Reagent: HX (X= halogen)

• adding the ROOR (peroxide) reagent gives the anti-Markonikov

• rearrangement possible (in Markovnikov)

Halohydrination

Reagents: Br₂ / H₂O

Adds: Br and OH (OH to more substituted)

Hydroboration Oxidation

Reagents:

• Step 1: BH₃ + THF

• Step 2: H₂O₂ + NaOH (aq) + H₂O

Adds: H + OH (OH → less substituted)

Oxymercuration Demurcuration

Reagents

• Step 1: Hg(OAc)_2, H₂O

• Step 2: NaBH₄

Adds: H + OH (OH → more substitued)

Hydrogenation

Reagent: H₂

Catalyst: Pd/C, Pt, or Ni

Adds: H + H

Anti Dihydroxylation

• Step 1: mCPBA

• Step 2: H₃O⁺

Adds: OH + OH (anti)

Syn Dihydroxylation

Reagents: O_sO₄ / Na₂SO₃, H2O

OR KmNO₄ (cold) / NaOH

Oxidative Cleavage

Reagents

1. O₃

2. DMS

Acid-Catalyzed Hydration

Reagent: H₃O⁺ (often written as H₂SO₄ + H₂O)

alkyne → cis alkene

H₂ / Lindlar’s catalyst

alkyne → trans alkyne

Na / NH₃ (l)

Alkyne → aldehyde

9-BBN / H₂O₂, NaOH, H₂O

Alkyne → ketone

H_gSO₄ , H₂O / H₂SO₄

alkyne → carboxlic acid

O₃ / H₂O

Which Reaction can Undergo a Carbocation Rearrangement?

E1, SN1, Acid catalyzed, hydrohalgenation

Alkyne full reduction

H₂ / Pd

What reactions behave the same for both alkenes and alkynes?

Hydrogenation, Halogenation, hydrohalogenation

What is epoxidation

A 3 membered ring with O

• reagent mCPBA

only happens with alkenes

SN2 kinetics, thermodynamics, and energy diagram

Kinetics: rate = k[substrate][nucleophile]

Thermodynamics

Explain how many products each reaction usually gives

SN₂ → always only one product

SN1 → two products if chiral center is formed

E₂ → never enantiomers sometimes distereoisomers (E vs Z)

E₁ → never enantiomers, sometimes distereoisomers