OAT Booster Organic Chemistry Reactions

Comprehensive vocabulary flashcards covering Substitution, Elimination, Alkene, Alkyne, Aromatic, and Carbonyl reactions based on the OAT Booster Organic Chemistry Reaction Sheet.

$S_N2$ reactions

Bimolecular substitution where less steric hindrance of substrate makes reaction faster; causes inversion of stereochemistry and uses a pentavalent transition state with a central carbon approximately $sp^2$ hybridized. Rate Law = $k[\text{substrate}][\text{nucleophile}]$.

$E2$ reactions

Bimolecular elimination where the leaving group and $H$ atom must be anti-periplanar. Small bases favor the Zaitsev product (more substituted), while bulky bases favor the Hofmann product (less substituted). Rate Law = $k[\text{substrate}][\text{base}]$.

$S_N1$ reactions

Unimolecular substitution requiring a weak nucleophile ($H_2O$, $ROH$); rearrangements are possible due to a carbocation intermediate stabilized by polar protic solvents. Rate Law = $k[\text{substrate}]$.

$E1$ reactions

Unimolecular elimination requiring a weak base ($H_2O$, $ROH$) and favoring the Zaitsev product; rearrangements are possible due to a carbocation intermediate. Rate Law = $k[\text{substrate}]$.

Catalytic Hydrogenation (Alkenes)

Reaction characterized by syn-addition stereospecificity, no regiospecificity, and no rearrangements.

Acid-Catalyzed Hydration

Reaction exhibiting no stereospecificity, Markovnikov regiospecificity, possible rearrangements, and a carbocation intermediate.

Oxymercuration-Demercuration

A reaction characterized as being stereorandom.

Alkoxymercuration-Demercuration

Reaction characterized by anti-addition stereospecificity, Markovnikov regiospecificity, no rearrangements, and a mercurinium ion intermediate.

Hydroboration-Oxidation

Reaction characterized by syn-addition stereospecificity, anti-Markovnikov regiospecificity, and no rearrangements.

Syn-Dihydroxylation

Reaction characterized by syn-addition stereospecificity, no regiospecificity, and no rearrangements.

Anti-Dihydroxylation

Reaction characterized by anti-addition stereospecificity, no regiospecificity, and no rearrangements.

Halogenation (Alkenes)

Reaction characterized by anti-addition stereospecificity, no regiospecificity, no rearrangements, and a bromonium ion intermediate.

Halohydrin Formation

Reaction characterized by anti-addition stereospecificity, Markovnikov regiospecificity, no rearrangements, and a bromonium ion intermediate.

Hydrohalogenation with peroxides (Alkynes)

Reaction characterized by no stereospecificity, anti-Markovnikov regiospecificity, no rearrangements, and a radical intermediate.

Free Radical Bromination

A regioselective free radical reaction.

Benzylic Bromination

A free radical reaction using $NBS$ to add bromine to the benzylic position.

Friedel Crafts Alkylation

An electrophilic aromatic substitution reaction where rearrangements are possible.

Benzylic Oxidation

A side-chain reaction that requires the presence of a benzylic hydrogen.

Wolff-Kishner Reduction

A reaction used for the reduction of aldehydes and ketones to alkanes.

Wittig Reaction

Treatment of an aldehyde or ketone with a phosphorus ylide to form an alkene.

Williamson Ether Synthesis

An $S_N2$ reaction used to synthesize ethers from an alkyl halide and an alkoxide.

Base-Catalyzed Opening of Epoxide

A reaction where the nucleophile attacks the less substituted side of the epoxide.

Acid-Catalyzed Opening of Epoxide

A reaction where the nucleophile attacks the more substituted side of the epoxide.

Hofmann Rearrangement

A reaction that results in the reduction of an amide to an amine with the loss of one carbon.

$SOCl_2$ Reaction

An $S_N2$ reaction used for converting $1^{\circ}/2^{\circ}$ alcohols to alkyl chlorides with inversion of stereochemistry.

Swern Oxidation

A reaction used to oxidize alcohols to aldehydes or ketones.

Haloform Reaction

A carbonyl alpha substitution reaction that only occurs with methyl ketones.

Dieckmann Condensation

An intramolecular Claisen condensation.

Organometallics (OAT)

Grignard reagents ($R\text{-}MgX$) and organolithium reagents ($R\text{-}Li$) are considered interchangeable in nucleophilic addition reactions.

Grignard Reagent + $CO_2$

A reaction that produces a carboxylic acid.