Reactions/reagents

Nitrile → Aldehyde

1)DIBAL 2) H₃O+

Acid Chloride → aldehyde

LiAlH(OtBu)

P ylide

 BuLi

Cyanohydrin

K/A + CN

Imine

K/A + 1° amine or ammonia

Acetal

2 equiv OH

Reaction + Deprotection

1) protecting group 2) NaBH4 2) H₃O⁺

Deoxygenation

add H₂ twice to K/A 

Hydrolysis of Imines

H₃O⁺/heat break 2 bonds and add water

Oxidation 1° OH → aldehyde

PCC 

NaOCl - TEMPO

Oxidation  1° OH → carboxylic acid

Na₂Cr₂O₇/H₂SO₄

Excess NaOCl - TEMPO

Oxidation  2° OH → ketone

PCC

NaOCl-TEMPO

Na₂Cr₂O₇/H₂SO₄

Reduction - carboxylic acid

LiAlHOtBu

Reduction- NaBH4

Ketones → 2° OH

Aldehydes → 1°  OH

Hydrogenation w/ cat

Carbonyl → OH, any double/single bonds are also reduced 

Exhaustive alkylation

amine + 3CH₃-halogen + NaHCO₃ → tetraalkylammonium salt

Alkyl halide alkylation

2°  amine + 1°  halide → (SN2)

sulfonamide

 1° or 2°  amine + sulfonyl chloride

Ammonium salts

R₃N + aq. HCl → R₃NH Cl^- 

Backwards: aq. NaOH

Acylation of Amines

Acid chloride + amine + pyridine → amide

Aromatic acylation

aniline + acid chloride + dilHNO₃/H₂SO₄ → benzene w/ NH₂ on top and NO₂ on bottom

Hoffman elimination (E2)

aniline + 1)CH₃I/ 2) Ag₂O → 6-membered ring w/ 1 double bond and nothing attached 

*Sigma bond must rotate to staggered conformation for E2 mech to occur

Amine oxides

3° amine + (any of 3 below) → 3° amine attached to O^-

H₂O₂

ArCO₃H

R-CO₃H

Cope (E2)

amine oxide acts as its own base through cyclic transition state, therefore strong base not needed

Arenediazonium salts

toluene + HNO₃/H₂SO₄ → 1)Fe/HCl/ 2) ^-OH → NaNO₃/HCl → various reagents → toluene w/ Z on other end

Various reagents

H₃O⁺ → Ar-OH

CuCl → Ar-Cl 

CuBr → Ar-Br 

CuCN – Ar-CN 

HBF₄ → Ar-F

KI → Ar-I

H₃PO₄ → Ar-H

Sandmeyer rxn

Ar-N≡NCl^- + CuX (X = Cl, Br, C≡N) → Ar-X + N₂

Reductive amination - 1° amines

K/A + H₂N-OH/H⁺ → oxime + LiAlH₄  (reduction) → 1° amine

Reductive amination - 2° amines

K/A + 1° amine → LAH (reduc.) → 2° amine

Reductive amination - 3° amines

K/A 2° amine → LAH (reduc) → 3° amine

Acylation - Reduction 1° amines

acid chloride + ammonia → 1° amide + 1)LIALH/ 2) H₂O → 1° amine  

Acylation - Reduction 2° amines

acid chloride + 1° amine → 2° amide + 1)LIALH/ 2) H₂O → 2° amine 

Acylation - Reduction 3° amines

acid chloride + 2° amine → 3° amide + 1)LIALH/ 2) H₂O → 3° amine   

Reduction of azides → 1° amine

benzene w/ ethylbromide + NaN₃ → br replaced w/ N₃ + 1)LiALH/ 2)H₂O → benzene w/ ethyl attached to NH₂

Reduction of Nitriles  →  1° amine

halide + CN → R-CN + LiALH₄/or cat. H₂ → 1° amine