Alcohol+HX

-H adds to OH and makes it better leaving group

-Usually SN1 unless SOCl₂ or PBr₃ are used

-SOCl₂ and PBr₃ cause inversion (SN2)

Ether-------->alkyl halide

Ether+2HX

-ROR' splits to form two separate alkyl halides

Alkene+HX

-Adds according to Markovnikov's Rule unless HBr in presence of peroxides

Alkyl halide+^-OH

-Regular Substitution

Epoxide+Acid (HA)

-Acid attacks more substituted side

-H adds to oxygen

-OR-

Epoxide+1.STRONG Nu:^-

2.H₂O

-Nu adds to less sub side

Alkene+H₂O/H₂SO₄ (Markovnikov's Rule)

-OR-

Alkene+1.BH₃

                             2.H₂O₂/OH^-(A-MR)

Alkene+1.RCO₃H

                         2.H₂O (OH^- or H⁺)

-Epoxidation followed by ring-opening

Alkene+KMnO₄/H₂O, OH^-

-OR-

Alkene+1.OsO₄

                       2.NaHSO₃, H₂O

Alkene+X₂ in presence of H₂O

-OH attacks more sub side

Alkyl halide+1.LiAlH₄

                2.H₂O

Alkene (or alkyne)+(2)H₂ on solid Pd-C

-Catalytic addition

Alcohol+H₂SO₄ (or tosic acid)(and heat)

-OR-

Alcohol+POCl₃ (in pyridine)

Tosylate+bulky base (in heat)

-E₂

Alkene+ Na (in NH₃(l))

-Dissolving metal reduction

Dihalide+2NH₂^-

-OR-

2 ^tBuO^- (in DMSO)

-Two separate E₂ reactions

Terminal alkyne+1.BH₃

                                2.H₂O₂/OH^-

-Anti Markovnikov's Rule

INTERNAL Alkyne+1.BH₃

                                  2.H₂O₂/OH^-

-OR-

Alkyne (either)+H₂O/H₂SO₄

Ether+H-X

-If R groups are differenct (ROR') will create mixture of 4:

1.RO

2.XR'

3.R'O

4.XR

Secondary alcohol+any Cr⁶⁺ reagent

-Cr⁶⁺ Reagents:

CrO₃/H₂SO₄

Na₂Cr₂O₇/H₂SO₄

K₂Cr₂O₇/H₂SO₄

Alkene+1.O₃

                                   2.Zn/H₂O or CH₃SCH₃

-Splits alkene (ozonolysis)

Alkyne+1.O₃

             2.H₂O

-Internal makes two carboxylic acid molecules

-Terminal makes carboxylic acid and CO₂

Primary Alcohol+Oxidizing Agent

-can also make an aldehyde (PCC in CH₂Cl₂)

-Oxidized by Na₂Cr₂O₇, CrO₃, or K₂Cr₂O₇ in H₂O/H₂SO₄

S_N2: 2 Primary alcohols+H₂SO₄ (and heat)

-OR-

2 Primary alcohols+H⁺

-OR-

Asymmetrical: Alcohol+Strong base+R'-X