Organic Chemistry Review: Hydrocarbons, Reaction Mechanisms, Functional Groups, and Named Reactions

Comprehensive vocabulary flashcards covering named organic reactions, functional group preparations, reagents, and mechanisms from the lecture notes.

Sabatier & Senderens Reaction

The catalytic hydrogenation of alkenes or alkynes to alkanes using Raney nickel catalyst at elevated temperatures.

Corey-House Synthesis

A method for coupling alkyl halides using lithium dialkyl cuprate ($R_2CuLi$) to form alkanes; the reagent does not react with $-NO_2$, $-CN$, or carbonyl groups.

Frankland's Reagent

A dialkylzinc reagent formed by treating alkyl halides ($R\text{-}X$) with zinc metal in dry ether to yield symmetrical alkanes ($R\text{-}R + ZnX_2$).

Lindlar's Catalyst

Metallic palladium deposited on calcium carbonate ($Pd/CaCO_3$) and poisoned with lead acetate or quinoline; used for the syn-addition of hydrogen to alkynes to synthesize cis-alkenes.

Birch Reduction of Alkynes

The partial reduction of non-terminal alkynes using sodium or lithium in liquid ammonia ($Na/\text{liq. } NH_3$) via anti-addition to synthesize trans-alkenes; it does not work with terminal alkynes.

Hydroboration-Oxidation

An anti-Markovnikov hydration method for alkenes using diborane ($B_2H_6/\text{THF}$) followed by alkaline hydrogen peroxide ($H_2O_2/OH^-$) to produce primary alcohols.

Oxymercuration-Demercuration (OMDM)

A two-step hydration of alkenes using $Hg(OAc)_2/\text{THF}/H_2O$ followed by reduction with $NaBH_4/H_2O$ that produces Markovnikov alcohols without carbocation rearrangement.

Swarts Reaction

A halogen-exchange method for synthesizing alkyl fluorides ($R\text{-}F$) by heating alkyl halides ($R\text{-}X$) with inorganic fluorides like silver fluoride ($AgF$).

Lucas Reagent

A mixture of concentrated hydrochloric acid and anhydrous zinc chloride ($\text{conc. } HCl + \text{anhyd. } ZnCl_2$) used to classify alcohols based on turbidity rate ($3^\top$ alcohols react immediately, $2^\top$ within $5\text{--}10\text{ minutes}$, and $1^\top$ require over $30\text{ minutes}$).

Finkelstein Reaction

A nucleophilic substitution halogen-exchange reaction where alkyl chlorides or bromides are treated with sodium iodide ($NaI$) in dry acetone to prepare alkyl iodides.

Darzens Process ($S_Ni$ Reaction)

The chlorination of alcohols using thionyl chloride ($SOCl_2$) in ether, proceeding with retention of configuration through an internal nucleophilic substitution ($S_Ni$); adding pyridine changes the mechanism to $S_N2$ with inversion of configuration.

Williamson Ether Synthesis

The reaction of an alkoxide ion with a primary alkyl halide via an $S_N2$ mechanism to produce an ether; using secondary or tertiary alkyl halides yields alkenes as elimination products instead.

Pinacol-Pinacolone Rearrangement

The acid-catalyzed dehydration of a vicinal diol (pinacol) involving carbocation formation, a methyl shift, and keto-enol stabilization to yield a ketone (pinacolone).

Bouveault-Blanc Reduction

The reduction of aldehydes, ketones, or esters to their corresponding alcohols using sodium in ethanol ($Na/\text{EtOH}$).

Baeyer's Reagent

A cold, dilute $1\%$ alkaline solution of potassium permanganate ($KMnO_4$) used as a test for unsaturation, converting alkenes into cis-1,2-diols via syn-hydroxylation.

Stephen's Reduction

A selective reduction of nitriles to aldehydes using acidified stannous chloride ($SnCl_2/HCl$) followed by imine hydrolysis with water.

Popoff's Rule

A guiding principle in the destructive oxidation of unsymmetrical ketones stating that the carbonyl group preferentially stays attached to the smaller alkyl group upon carbon-carbon bond cleavage.

Etard Reaction

The selective oxidation of toluene and its methyl derivatives to benzaldehydes using chromyl chloride ($CrO_2Cl_2$) in carbon disulfide ($CS_2$) or $CCl_4$ followed by hydronium ion ($H_3O^+$) hydrolysis.

Wacker Process

The industrial oxidation of ethene to acetaldehyde using palladium(II) chloride ($PdCl_2$) with a catalytic amount of cupric chloride ($CuCl_2$) in the presence of water and oxygen or air.

Dow's Process

An industrial method for preparing phenol by heating chlorobenzene with aqueous sodium hydroxide ($NaOH$) at high temperature and high pressure.

Kolbe-Schmitt Carboxylation

The carboxylation of sodium phenoxide with carbon dioxide ($CO_2$) under heat and pressure, followed by acidification to produce salicylic acid as the major product.

Reimer-Tiemann Reaction

The ortho-formylation of phenol by treatment with chloroform ($CHCl_3$) and aqueous alkali ($NaOH$ or $KOH$) followed by acidification to yield salicylaldehyde.

Fries Rearrangement

The conversion of phenyl esters into a mixture of ortho- and para-hydroxyacetophenones upon heating in the presence of anhydrous aluminum chloride ($AlCl_3$).

Libermann's Nitroso Test

A chemical identification test for phenols involving reaction with sodium nitrite ($NaNO_2$) and concentrated sulfuric acid ($H_2SO_4$), producing a red or brown indophenol complex that turns deep blue upon adding excess alkali ($NaOH$).

Gabriel Phthalimide Synthesis

A synthetic pathway for preparing pure aliphatic primary amines by alkylating potassium phthalimide with an alkyl halide via an $S_N2$ displacement, followed by acidic or basic hydrolysis.

Hofmann Bromamide Decarboxylation

The degradation of a primary acid amide into a primary amine with one fewer carbon atom by treatment with bromine ($Br_2$) and aqueous potassium hydroxide ($KOH$).

Hinsberg Reagent

Benzenesulfonyl chloride ($PhSO_2Cl$), utilized to differentiate primary, secondary, and tertiary amines based on the solubility of their sulfonamide products in aqueous alkali.

Carbylamine Test

A diagnostic test for aliphatic and aromatic primary amines performed by warming with chloroform ($CHCl_3$) and alcoholic $KOH$, producing an extremely foul-smelling isocyanide (carbylamine).

Balz-Schiemann Reaction

The synthesis of aryl fluorides by precipitating benzenediazonium tetrafluoroborate with fluoroboric acid ($HBF_4$) and thermally decomposing the isolated diazonium salt.

Sandmeyer Reaction

The substitution of the diazonium group in benzenediazonium salts with chlorine, bromine, or cyano groups using cuprous salts ($CuCl$, $CuBr$, or $CuCN$) in the corresponding hydrohalic acid.

Cannizzaro Reaction

The base-catalyzed disproportionation of aldehydes lacking an $\alpha$-hydrogen in concentrated alkali ($50\%\, NaOH$ or $KOH$) into an equimolar mixture of a primary alcohol and a carboxylic acid salt.

Perkin Reaction

The condensation of an aromatic aldehyde lacking an $\alpha$-hydrogen with an aliphatic acid anhydride in the presence of its corresponding sodium carboxylate salt under heat to form an $\alpha,\beta$-unsaturated aromatic acid (such as cinnamic acid).

Reformatsky Reaction

The reaction of an aldehyde or ketone with an $\alpha$-halo ester in the presence of metallic zinc in dry ether, followed by aqueous hydrolysis to form a $\beta$-hydroxy ester.

Wittig Reaction

The coupling of an aldehyde or ketone with a triphenylphosphonium ylide ($R\text{-}CH=PPh_3$) to stereoselectively generate an alkene and triphenylphosphine oxide ($Ph_3P=O$).

Baeyer-Villiger Oxidation

The oxidative insertion of an oxygen atom adjacent to the carbonyl carbon in ketones using peroxy acids ($R''COOOH$) to yield esters or lactones.

Hell-Volhard-Zelinsky (HVZ) Reaction

The selective $\alpha$-halogenation of aliphatic carboxylic acids with chlorine or bromine in the presence of a catalytic amount of red phosphorus ($\text{Red } P$).