ORGO 2 Naming

Thiol (Mid Low under OH)

• Naming:

  • Ending: “-thiol” (IUPAC)

  • As substituent: “mercapto-”

• Formula: R–SH

• Examples:

  • Butanethiol (CH₃CH₂CH₂CH₂SH)

  • Mercaptoethanol (HOCH₂CH₂SH)

• Used for: Form disulfides, can act as nucleophiles in SN2 reactions, synthesize thiolates

Ether

• Naming:

  • IUPAC: name both sides + “ether” or use “alkoxy” as a substituent

• Formula: R–O–R'

• Examples:

  • Diethyl ether

  • Methoxyethane

• Used for: Williamson ether synthesis, acid-catalyzed condensation, alkoxymercuration, cleavage with HX

Epoxide

• Naming:

  • IUPAC: “oxirane” or as “epoxy” substituent

• Formula: Three-membered cyclic ether

• Examples:

  • Ethylene oxide (oxirane)

  • 1,2-Epoxybutane

• Used for: Nucleophilic ring opening (acid/base), synthesis from halohydrins

Crown Ethers

• Group: Crown Ether

• Naming: “#-crown-#” format

• Formula: Cyclic polyethers

• Examples:

  • 12-crown-4 (binds Li⁺)

  • 15-crown-5 (binds Na⁺)

  • 18-crown-6 (binds K⁺)

• Used for: Solvate metal cations, phase transfer catalysis

Disulfides

• Group: Disulfide

• Naming: “disulfide” suffix

• Formula: R–S–S–R

• Examples:

  • Dimethyl disulfide (CH₃–S–S–CH₃)

• Used for: Redox reactions with thiols (I₂, NaBH₄/Zn-acid)

Sulfoxides & Sulfones

Sulfoxides & Sulfones

• Group: Sulfoxide / Sulfone

• Naming: Named like ketones or as substituents

• Formula:

  • Sulfoxide: R–S(=O)–R'

  • Sulfone: R–S(=O)₂–R'

• Examples:

  • Dimethyl sulfoxide (DMSO)

  • Dimethyl sulfone

• Used for: Solvents, oxidized thiols/sulfides

Aldehydes (medium above ketone)

• Group: Aldehyde

• Naming: “-al”, “-oxo” for lower

• Formula: R–CHO

• Examples:

  • Propanal

  • Benzaldehyde

• Used for: Hydration, imine/enamine formation, acetal formation, Wittig reaction, oxidized to carboxylic acids

Ketone (medium below aldehyde)

Ketones

• Group: Ketone

• Naming: “-one”, “oxo” if less

• Formula: R–CO–R'

• Examples:

  • Butanone

  • 2-oxo-propenal

• Used for: Same as aldehydes, but cannot oxidize further

Cyanohydrin

• Group: Cyanohydrin

• Naming: Not typically IUPAC named; described functionally

• Formula: R₂C(OH)(CN)

• Example: 2-hydroxyethanenitrile

• Used for: Formed from aldehydes/ketones + HCN, can be reduced to amino alcohols

Imines (lowest)

• Group: Imine

• Naming: “-animine” or “Schiff base”

• Formula: R₂C=NR'

• Examples:

  • Ethanimine

• Used for: From aldehydes/ketones + primary amines

Enamines

• Group: Enamine

• Naming: En- + amine

• Formula: C=C–NR₂

• Examples:

  • propenamine

  • Used for: Synthesized from aldehydes/ketones + secondary amines

Hydrazones / Oximes

• Group: Hydrazone, Oxime

• Naming: named at the end

• Examples:

  • Oxime: R₂C=NOH

  • Hydrazone: R₂C=NNH₂

• Used for: Characterization, used in Wolff-Kishner reduction

Acetals / Hemiacetals

• Group: Acetal / Hemiacetal

• Naming: Functional descriptor, not distinct suffix

• Formula:

  • Acetal: R₂C(OR)₂

  • Hemiacetal: R₂C(OH)(OR)

• Examples:

  • 1,1-Dimethoxyethane

• Used for: Protecting groups, reversible under acid

Carboxylic Acids (highest raking)

• Group: Carboxylic acid

• Naming: “-oic acid”

• Formula: R–COOH

• Examples:

  • Butanoic acid

  • Benzoic acid

• Used for: Synthesis of derivatives, decarboxylation, acidic group (pKa ~5)

Nitriles (medium above aldehyde)

• Group: Nitrile

• Naming: “-nitrile” or “-carbonitrile”

• Formula: R–C≡N

• Examples:

  • Butanenitrile

  • Benzonitrile

• Used for: Converted to amines, carboxylic acids, or ketones

Acid Chlorides

• Group: Acyl halide

• Naming: “-oyl chloride”

• Formula: R–COCl

• Examples:

  • Ethanoyl chloride

• Used for: Synthesis of amides, esters, ketones (via organocuprates)

Anhydrides

• Group: Anhydride

• Naming: “-oic anhydride” or “chloroformyl”

• Formula: R–CO–O–CO–R

• Examples:

  • Acetic anhydride

  • 3-chloroformylethanoic acid

• Used for: Synthesis of esters, amides

Esters below COCl

• Group: Ester

• Naming: “Alkyl carboxylate”

• Formula: R–COOR'

• Examples:

  • R’ Roate

  • Ethyl propanoate

• Used for: Hydrolysis, DIBAL reduction to aldehydes

Amides (below COOR)

• Group: Amide

• Naming: “-amide.” if substituent use N (see below)

• Formula: R–CONH₂ or R-CONHR

• Examples:

  • Propanamide

  •   N-ethyl-N-Methylpropamide (Alphabetic)

• Used for: Dehydrated to nitriles, reduced to amines

Lactones / Lactams

• Group: Cyclic esters (lactones) or amides (lactams)

• Naming: “-lactone” / “-lactam”

• Examples:

  • γ-Butyrolactone

  • β-Lactam

• Used for: Found in natural products and drugs (e.g., penicillin)

Carbohydrates

• Group: Sugars

• Naming: Based on # of carbons, aldose/ketose, D/L, pyranose/furanose, alpha or beta

• Examples:

  • D-Glucose, α-D-glucopyranose

• Used for: Understand structure, stereochemistry, mutarotation

Hydrates (gem diol)

• Group: Hydrate (geminal diol)

• Naming: Generally no special IUPAC name; named as hydrated form of aldehyde or ketone (e.g., “hydrate of formaldehyde”)

• Formula: R₂C(OH)₂

• Example: Methanediol (hydrate of formaldehyde)

• Used for: Formed by hydration of aldehydes/ketones under acidic or basic conditions; important intermediate in carbonyl chemistry and nucleophilic addition reactions

Pyridine

• Group: Aromatic six-membered ring heterocycle with nitrogen

• Naming: Common name only

• Formula: C₅H₅N

• Example: Pyridine

• Used for: Base, solvent, ligand in coordination chemistry

Pyrrole

• Group: Aromatic five-membered ring heterocycle with nitrogen

• Naming: Common name only

• Formula: C₄H₅N

• Example: Pyrrole

• Used for: Aromatic heterocycle, biological molecules (heme, chlorophyll)

Furan

• Group: Aromatic five-membered ring heterocycle with oxygen

• Naming: Common name only

• Formula: C₄H₄O

• Example: Furan

• Used for: Heterocyclic aromatic compound, substrate in electrophilic substitution

Phosphorus Ylides

(PPh₃)

• Group: Organophosphorus reagent

• Naming: Triphenylphosphine

• Formula: (C₆H₅)₃P

• Used for: Wittig reaction (forms phosphorus ylides), reduction reactions

Sulfone

• Group: Sulfone functional group

• Naming: “-sulfone” suffix

• Formula: R–S(=O)₂–R'

• Example: Diphenyl sulfone

• Used for: Stable oxidation product of sulfides/sulfoxides

Sulfoxide

• Group: Sulfoxide functional group

• Naming: “-sulfoxide” suffix or “sulfinyl-” as substituent

• Formula: R–S(=O)–R'

• Example: Dimethyl sulfoxide (DMSO)

• Used for: Polar aprotic solvent, oxidation intermediate

THF ****

Tetrahydrofuran (THF)

• Group: Cyclic ether (5-membered ring with oxygen)

• Naming: Common name only

• Formula: C₄H₈O

• Example: Tetrahydrofuran

• Used for: Common solvent, reagent in ring-opening reactions

THP ****

Tetrahydropyran (THP)

• Group: Cyclic ether (6-membered ring with oxygen)

• Naming: Common name only

• Formula: C₅H₁₀O

• Example: Tetrahydropyran

• Used for: Protecting groups for alcohols, ring formation studies

Sulfide

• Group: Sulfide (thioether)

• Naming: Like ethers, name both alkyl groups + “sulfide” (e.g., ethyl methyl sulfide), or use “alkylthio-” as a substituent

• Formula: R–S–R'

• Example: Dimethyl sulfide (CH₃–S–CH₃)

• Used for: Analogous to ethers but with sulfur; found in biological molecules, can be oxidized to sulfoxides or sulfones

Catrbox acid derivatives with nucleophile

RCOY where Y is O,N,S,Cl

• Naming: change ic acid to -yl and add name + ate

• Ex:  Ethyl butanethioate