Reactions, Reagents, and Products

Alcohols to Alkyl Halides (Rearrangement)

Heat and HX (Best for tertiary alcohols) [also H2SO4 and NaX may be used]; Uses Sn1 and Sn2 processes (Umbrella Flipping)

Alcohols to Alkyl Halides (NO rearrangement)

SOX2 (best method for 1 and 2 alkyl chlorides); PX3 (Best method for 1 and 2 alkyl bromides; P/I2 for 1 and 2 alkyl iodides)

Alkanes to Alkyl Halides

X2 and Heat or Light (hv); Uses radical process (can be sped up by peroxides); too difficult for F2 and I2, only Cl2 and Br2 really

Alkanes to Alkyl Bromides (to avoid using Br2)

NBS (See reaction notebook) and heat or light (hv)

Alkyl Halides to Alkenes (E1)

Weak Base (H2O, CH3OH) and heat; Good for 2 and 3 halides

Alkyl Halides to Alkenes (E2)

Strong Base (-NH2, NaOCH2CH3 for Zeitsev Product; KOC(CH3)3 for Non-Zeitsev Product); Exclusive process for 1 halides

Alcohols to Alkenes (E1)

H3PO4 or H2SO4 (To avoid halide side products) and Heat

Alcohols to Alkenes (E2)

H3PO4 or H2SO4 (To avoid halide side products) and Heat

Alkenes to Alkanes (Favoring Syn Addition)

Catalyst Metal (Pt, Pd, Ru, Ni), Heat, and Pressure

Alkenes to Alkyl Halides (Markovnikov Product)

HX

Alkenes to Alcohols

H2O and H2SO4 or H3PO4 (In solution, these become H3O+ and HSO4- or H2PO4-)

Alkenes to Alkyl Dihalides (anti-stereoselectivity)

X2

Alkenes to Alkyl Halides (anti-Markovnikov product)

HX, Peroxide, and heat or light (hv)

Alkenes to Halohydrins

X2 (Low concentration) and H2O (High concentration)

Halohydrins to Epoxides

Strong Base (NaOH)

Alkenes to Alcohols or Ethers

1. Hg(OAc)2; H2O or ROH
2. NaBH4

Alkenes to Diols (Syn addition)

OsO4, NaHSO3, and H2O

Alkenes to Aldehydes or Ketones

1. O3
2. H3C--S--CH3 (DMS: Dimethyl Sulfide)

Alkenes to Alcohols (anti-Markovnikov; syn addition)

1. BH3 (Found as B2H6 dissolved in THF--Tetrahydrofuran)
2. H2O2, NaOH

Alkenes to Epoxides (w/o halohydrin)

Peroxy acids (m-chloroperoxybenzoic acid, peroxyacetic acid for organic solns; Mg monoperoxyphthalate for aq. solns.) or Ag and O2 (will NOT work on lower mol. wt. compounds-exception is ethylene)