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Carboxylic acid to carboxylate
Reagent: Strong base (NaOH), Product: Carboxylate salt (R—COO⁻ M⁺)
Primary alcohol to carboxylic acid
Reagents: Na2Cr2O7, H2SO4
Alkene to carboxylic acid
Alkene + concentrated KMnO4
Alkene to ketone
Alkene with two carbons + concentrated KMnO4
Alkyne to carboxylic acid
Concentrated KMnO4 OR O3/H2O
Adding carbons to carboxylic acid chain (Grignard)
R-MgBr + CO2
Adding carbons to carboxylic acid chain (nitrile)
R-X + NaCN → R-CN, then reacts with H+ to form carboxylic acid
Ester to carboxylate
Base (OH-)
Fischer Esterification
Acid + alcohol → H+
Carboxylic acid to methyl ester
CH2N2
Carboxylic acid to amide
R-NH2 (amine) + heat
Reduces carboxylic acids to aldehydes
Thionyl chloride (SOCl₂) + Lithium aluminum hydride (LiAl(Ot-Bu)₃)
Carboxylic acid to ketones
Lithium carboxylate (2R-Li) + H2O
Converts carboxylic acids to acid chlorides
Thionyl chloride (SOCl₂)
Esterification- Carboxylic acid to ester (acyl chloride)
Carboxylic acid + SOCl2 → acid chloride, then reacted with R-OH to displace Cl and add OR group
Acid chloride to amide
R-NH2 + NaOH
Acid chloride to anhydride
Add carboxylic acid
Acid chloride to ester
Add alcohol
Anhydride to carboxylic acid
Add water
Anhydride to carboxylate
Add a nucleophile, splits into two forming carboxylate
Anhydride to Ester
Add alcohol
Anhydride to Amide
Add NH2
Special anhydride
Will be attacked at the aldehyde spot
Making lactones
Carbon chain with COOH and OH, add H+ to join
Esters/acids/acyl chlorides to alcohol
LiAlH4 and H+
Esters to aldehydes
DIBAL, H2O
Ester to amide
Nucleophile NH3 or primary amine
Ester to carboxylic acid
H2O, H+
Amide to amine
LiAlH4/H2O
Making Lactams
Carboxylic acid chain with NH2 turns into lactam with heat
Amides to nitriles
POCl3
Amides to Carboxylic acid
H2O, H+
Nitriles to amide
NaOH/H2O/etOH, heat
Nitrile to amines
LiAlH4/H2O
Nitrile to ketone
RMgX, H3O+
Nitrile to carboxylic acid
H2O, H+
Nitrile to aldehyde
DIBAL, H3O+
Tertiary amine to amine oxide
H2O2
Cope rearrangement
Internal E2 attack with base and H to form an alkene
Formation of diazonium salt
Primary amine + HNO2
Reactions of arenediazonium salts
H3O+>OH; CuCl/Br/CN; HBF4, KI, H3PO2 adds hydrogen; H=Ar" adds aromatic ring to double bond of two nitrogens
Reductive amination of primary amines, ketone/aldehyde to primary amine
Ketone/aldehyde + H2N-OH, LiAlH4
Reductive amination of secondary/tertiary amines ketone/aldehyde to secondary/tertiary amine
Ketone/aldehyde + R-NH/R-NH-R, LiAlH4
Synthesis of primary/secondary/tertiary amines
Acid chloride + NH3/R-NH2/R2-NH
Reduction of Azides to NH2
-N3 to R-X, then LiAlH4
Reduction of nitriles
CN- to R-X (SN2), then LiAlH4
Reduction of nitro compounds
Zn, HCl, OH-
Note 
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