Organic Chemistry RCC Notes - Vocabulary flashcards

A set of vocabulary-style flashcards covering key terms and concepts from the RCC Organic Chemistry lecture notes.

Aldol condensation

A base-catalyzed reaction between an aldehyde or ketone bearing an α-hydrogen to give a β-hydroxy aldehyde/ketone (aldol), which may dehydrate to form an α,β-unsaturated carbonyl compound.

Cross aldol condensation

Aldol reaction between two different carbonyl compounds (each with at least one α-hydrogen), giving mixed products and often α,β-unsaturated carbonyl compounds.

Intramolecular aldol condensation

Aldol reaction that occurs within a single molecule, often leading to ring formation; ring priority rules may apply (e.g., 6 > 5 > 7 in cyclization).

Cannizzaro reaction

Disproportionation of aldehydes lacking α-hydrogens in strong base to yield a mixture of an alcohol and a carboxylate salt.

Wurtz reaction

Reaction of two alkyl halides with sodium in dry ether to form a symmetric alkane plus NaX; prefers 1°–3° reactivity with limitations on odd-numbered chains.

Wurtz-Fitting reaction

Extension of Wurtz involving aryl halides with alkyl halides under Na/dry ether to form aryl-alkyl combinations (Fitting variant).

Kolbe’s electrolysis

Electrolysis of sodium salts of carboxylic acids to give alkanes with longer carbon chains, with CO2 evolving at the anode and H2 at the cathode.

Friedel–Crafts alkylation

Electrophilic aromatic substitution where an alkyl halide reacts with benzene in the presence of a Lewis acid (e.g., AlCl3) to give alkylbenzene; rearrangements of carbocation can occur.

Friedel–Crafts acylation

Electrophilic aromatic substitution where an acyl chloride (or anhydride) reacts with benzene in the presence of AlCl3 to yield a diaryl ketone (aryl ketone).

Finkelstein reaction

SN2 halogen exchange where R–X reacts with NaI in acetone to give R–I (iodide) and NaX; typically used to prepare alkyl iodides.

Swarts reaction

Halogen exchange using AgF/HgF2, SbF3, or CoF2 to replace halogens with fluorine, forming alkyl fluorides via SN2-type mechanism.

Beilstein test

A qualitative test for halogens using copper wire; a green flame indicates the presence of halogens in an organic compound.

Lucas reagent

A solution of ZnCl2 in concentrated HCl used to differentiate 1°, 2°, and 3° alcohols by rate of turbidity formation.

Iodoform test

Reaction for methyl ketones (R-CO-CH3) and some alcohols to give a yellow CHI3 precipitate under basic conditions.

Carbylamine test

Test for primary amines where CHCl3 and base form an isocyanide (unpleasant odor); secondary/tertiary amines do not give this test.

Hinsberg test

Qualitative test for amines using Hinsberg reagent (sulfonyl chloride); differentiates primary, secondary, and tertiary amines by solubility in base or acid.

Sandmeyer reaction

Conversion of aryl diazonium salts to other substituents (e.g., Cl, Br, CN, etc.) using Cu(I) salts, enabling aryl halide/ cyanide substitutions.

Gattermann reaction

Formylation of benzene using formylating agents (often HCN with Lewis acids) to give salicylaldehyde or related aldehydes.

Gattermann–Koch reaction

Formylation of benzene with CO and HCl in the presence of AlCl3/CuCl to yield benzaldehyde derivatives.

Reimer–Tiemann reaction

Formylation of phenols (typically phenol) using CHCl3 and NaOH to give o-hydroxybenzaldehyde (salicylaldehyde formation).

Rosenmund reduction

Partial reduction of an acyl chloride to the corresponding aldehyde using poisoned Pd catalyst (often Pd/BaSO4) and H2.

Etard reaction

Oxidation of methyl groups (e.g., toluene) to aldehydes via chromyl chloride (CrO2Cl2) complex, followed by hydrolysis.

Rosenmund–Knoevenagel?

Note: Noting a commonly cited variant; main concept is Rosenmund-type aldehyde formation via selective reduction of acyl chlorides.

Stephen reduction

A historical reductive method involving nitriles to give aldehydes/amines under reducing conditions; used for aldehyde synthesis in some contexts.

Etard reaction

(Listed above) Oxidation of benzylic methyl groups to benzaldehydes using chromyl chloride.

Clemmensen reduction

Reduction of carbonyl compounds (aldehydes/ketones) to alkanes using Zn(Hg) in concentrated HCl (acidic medium).

Wolf–Kishner reduction

Reduction of carbonyl compounds to alkanes under strongly basic, high-temperature conditions using hydrazine derivative and base.

Birch reduction

Partial reduction of alkynes to trans-alkenes (or conjugated systems) using liquid ammonia and alkali metals (e.g., Na/NH3).

Lindlar catalyst

Poisoned Pd catalyst (e.g., Pd/BaSO4 or Pd/CaCO3 with quinoline) used to stop hydrogenation at the alkene stage, giving cis-alkenes from alkynes.

Anti‑Markovnikov hydration

Hydration of alkenes via hydroboration-oxidation (BH3·THF then H2O2/NaOH) to yield anti‑Markovnikov alcohols.

Ozonolysis

Reaction of alkenes with ozone to form ozonides, which upon reduction or workup give aldehydes/ketones.

Baeyer–Villiger oxidation

Oxidation of ketones to esters using peracids or peroxides; migratory aptitude governs which group moves.

Permissible oxidation reagents KMnO4

Potassium permanganate used for oxidation; cold/basic yields diols or cleavage of double bonds; hot/strong oxidants give carboxylic acids.

Jones reagent

CrO3 in aqueous acetone (Jones oxidation); strong oxidant converting primary alcohols to carboxylic acids and secondary alcohols to ketones.

PCC (Pyridinium chlorochromate)

Mild oxidant for converting alcohols to carbonyls (1° to aldehyde, 2° to ketone) without overoxidation.

PDC (Pyridinium dichromate)

Mild oxidant for selective oxidation of alcohols to carbonyls with minimal overoxidation.

CAN (Ceric ammonium nitrate)

Mild oxidant used to oxidize benzylic alcohols and to oxidize certain organic substrates; can test for alcohols.

Aldol condensation vs Cannizzaro tests

Aldol requires α-hydrogen to participate; Cannizzaro does not require α-hydrogen and gives alcohol plus carboxylate.

Nitration (EAS)

Electrophilic aromatic substitution introducing NO2 onto an aromatic ring using HNO3/H2SO4 (or oleum).

Sulfonation (EAS)

Electrophilic aromatic substitution introducing –SO3H onto an aromatic ring using conc. H2SO4/sulfuric reagents.

Halogenation (EAS)

Electrophilic halogenation of arenes (Cl, Br) using FeCl3/AlCl3 (or Br2) as electrophile.

Friedel–Crafts alkylation (EAS)

Alkyl group introduction onto an aromatic ring using alkyl halide and Lewis acid (e.g., AlCl3); may rearrange carbocation.

Friedel–Crafts acylation (EAS)

Acyl group introduction onto an aromatic ring using acyl chloride/anion in presence of AlCl3 to give aryl ketones.

Markovnikov vs Anti‑Markovnikov

Markovnikov: H adds to less substituted carbon; Anti‑Markovnikov: H adds to more substituted carbon (often with peroxide in HBr) via radical mechanism.

Cyanohydrin formation

Nucleophilic addition of HCN to aldehydes/ketones giving cyanohydrins; cyanide adds to carbonyl carbon.

Beckmann rearrangement

Rearrangement of oximes under acidic conditions to give amides with migration of a group anti to the leaving hydroxyl.

Pinacol rearrangement

Acid-catalyzed rearrangement of vicinal diols (pinacol) to yield rearranged carbonyl products via carbocation rearrangement.

Oxyfunctionalization tests (Tollen’s, Benedict’s)

Tests to distinguish aldehydes from ketones: Tollens (silver mirror, aldehydes positive), Benedict’s/Fehling’s (Cu2O red ppt).

Glyoxal and Cannizzaro

Aldehydes without α-hydrogens (e.g., glyoxal) can undergo Cannizzaro-type disproportionation under base.

Glycoprotein structure terms

Nucleic acids: DNA/RNA; nucleosides (base attached to sugar), nucleotides (phosphate attached); base pairing A-T, G-C in DNA; A-U in RNA.

Aromaticity (Hückel’s rule)

A compound is aromatic if cyclic, planar, fully conjugated and contains 4n+2 π electrons (Hückel rule).