Exam 3

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47 Terms

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