Nucleophilic Acyl Attack (Carbonyl --> Alcohol)
LiAlH4/NaBH4, ketone/aldehyde, protic solvent
Oxidation of Alcohols
PCC, CH2Cl2
Grignard Reagents
Mg or Li, alkyl halide, Et2O
Alcohol Displacement
inorganic acid (PBr3, SOCl2, etc.)
Williamson Ether Synthesis
base (NaH), alkyl halide, aprotic solvent (DMF)
Ether Synthesis in Acidic Conditions
acid, heat (forms symmetric products only)
Epoxides in Basic Conditions
Nucleophile, epoxide, workup (attack less sterically hindered C and invert stereocenter)
Epoxides in Acidic Conditions
acid, epoxide, Nucleophile (attack more substituted side & invert stereocenter)
Sun-Addition of Hydrogens
Alkene, H2, catalyst: Pd/C, Pt/C, Ni/C
Markovnikov Addition of Hydro-Halides
H-X, alkene
Addition of Halogens
X-X, alkene, CH2Cl2 (racemic mixture)
Anti-Addition of Halohydrin
halogen, OR, alkene (attack more substituted side)
Hydration of Alkenes
H2O, catalyst (markovnikov)
Oxymercuration Reduction
1. Hg(OAC)2, H2O; 2. NaBH4, NaOH, H2O
Hydroboration Oxidation
BH3/THF, H2O2, NaOH, H2O (anti-mark, syn)
Epoxidation
mCPBA, CH2Cl2 (syn addition)
Anti-Diols
mCPBA, NaOH (anti addition)
Syn-Diols
OsO4, H2S (syn addition)
Ozonolysis
O3, CH2Cl2, DMS
Alkyne Reduction to Alkane
H2, Pd/C
Lindlar's Catalyst to form cis Alkene
H2, Lindlar
Birch Reduction to form trans Alkene
Na, NH3
Double Elimination
X2, Base (2 equivalent)
Alkyne Addition of H-X
excess HX (markovnikov
Alkyne Hydration
H2O
HgSO4 Hydration
HgSO4, H2O, H2SO4
Hydroboration Oxidation of Alkynes
1. Cy2BH/THF 2. NaOH, H2O2, H2O (anti-mark, syn addition)
Diels-Alder
heat, dienophile, diene
EAS Halogenation
X, AlX3
Friedel-Crafts Alkylation
R-X, AlX3
Friedel-Crafts Acylation
carbonyl, AlX3
Clemmenson Reduction
Zn(Hg), HCl
Carbonyl Hydration (acidic conditions)
H2O, H2SO4
Carbonyl Hydration (basic conditions)
H2O, NaOH
Carbonyl Addition of OR Groups
R-OH, H2SO4
Addition of Amines
carbonyl, R-NH2, H2SO4
Wolff-Kushner Reduction (deoxygenates carbonyl)
H2N-NH2, KOH, Heat
Making Enolates
carbonyl, LDA/THF
alpha-alkylation
LDA, THF, R-X
alpha-halogenation
AcOH, Br2
Aldol Reaction
aldehydes, NaOH, H2O
Aldol Condensation
aldehydes, NaOH, H2O, heat
Crossed Aldol
aldehydes, NaOH, heat, H2O
1. Making Carboxylic Acids & Derivatives
primary alcohol/aldehyde, CrO3, H2O, H2SO4
2. Making Carboxylic Acids & Derivatives
Organometallic Reagents MgBr
Acid Chlorides
SOCl2
Fischer Esterfication
ROH, H+
Amidation of Carboxylic Acids
R-NH2, heat
Reduction of Carboxylic Acids
LiAlH4, Et2O
Ester Hydrolysis (acidic conditions)
H2O, H2SO4, heat
Ester Hydrolysis (basic conditions)
H2O, NaOH, heat
Reactions of Acid Chlorides
H2O --> carboxylic acid ; ROH --> ester, NH2R --> amide
Transesterfication
ROH, H2SO4, heat
Amidation of Esters
RNH2, heat
Reduction of Esters (to primary alcohol)
LiAlH4, workup
Reduction of Esters (to aldehyde)
DIBALH, workup
Esters & Organometallic Reagents
R-MgBr
Amide --> Carboxylic Acid
H2O, H2SO4, high heat
Reduction of Amides
LiAlH4, workup