Exam 3

Carboxylic acid to carboxylate

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-