Organic Chemistry Reactions Practice Flashcards

Comprehensive practice vocabulary flashcards covering major Organic Chemistry I and II reactions, including naming, reagents, and mechanistic outcomes based on the lecture series by Chris Lovero.

Addition of HX (Markovnikov)

A reaction that adds a halide to the more substituted carbon of an alkene.

Addition of HX (Anti-Markovnikov)

A reaction using $HBr$ and $ROOR$ that adds a halide to the least substituted carbon of an alkene.

Oxymercuration-Demercuration

A complex mechanism using $Hg(OAc)_2 / H_2O$ and $NaBH_4$ that adds an hydroxyl group ($OH$) from an alkene with Markovnikov orientation and anti-planar stereochemistry.

Hydroboration-Oxidation

A reaction using $BH_3 / THF$ and $H_2O_2 / OH^-$ that adds an alcohol with Anti-Markovnikov orientation and syn-planar stereochemistry.

Simmons-Smith Reagent

Consists of $CH_2I_2$ and $Zn(Cu)$ used for carbene/carbenoid addition to form cyclopropane from alkenes with syn stereochemistry preserved.

Lindlar's Catalyst

A reagent composed of $H_2 / Pd(BaSO_4)$ and quinoline that isolates a cis-alkene from an alkyne via syn addition of $H_2$.

Dissolving Metal Reduction

The use of $Na / NH_3(l)$ to isolate a trans-alkene from an alkyne via anti addition of $H_2$.

Grignard Reagent

An organomagnesium reagent ($R-MgBr$) formed in ether that acts as a nucleophile to form alcohols from formaldehydes ($1^{ ext{o}}$), aldehydes ($2^{ ext{o}}$), or ketones ($3^{ ext{o}}$).

Gilman Reagent

An organometallic reagent $(R)_2CuLi$ used in the Corey-House reaction to attach carbon groups to acid chlorides or halides.

Jones Reagent

A harsh oxidizing mixture of $CrO_3 / H_2SO_4 / H_2O$ in acetone at $0^{ ext{o}}C$ that oxidizes primary alcohols to carboxylic acids and secondary alcohols to ketones.

PCC (Pyridinium Chlorochromate)

A mild oxidizing agent used in $CH_2Cl_2$ to oxidize primary alcohols to aldehydes without further oxidation to carboxylic acids.

Williamson Ether Synthesis

An $S_N2$ reaction between an alkoxide ion and a primary alkyl halide or methyl halide to form an ether.

Fischer Esterification

The acid-catalyzed reaction of a carboxylic acid with an alcohol to form an ester and water.

Diels-Alder Reaction

A pericyclic reaction between a diene and a dienophile under heat to form a substituted cyclohexene ($1,2$ or $1,4$ adduct) following the endo rule.

Birch Reduction

The reduction of benzene rings using $Na^0$ or $Li^0$ in $NH_3(l) / ROH$; electron withdrawing groups result in $sp^3$ carbons at the substituted positions, while electron donating groups result in $sp^2$ carbons.

Gatterman-Koch Formylation

The formation of benzaldehyde from benzene using $CO$, $HCl$, $AlCl_3$, and $CuCl$; it does not work on rings with strong deactivators or amino groups.

Clemmensen Reduction

A method using $Zn(Hg)$ and $HCl$ to reduce carbonyl groups to alkanes; should be avoided in the presence of alkenes, alkynes, alcohols, or amines.

Wolff-Kishner Reduction

A method using $NH_2NH_2$ and $KOH / DMSO$ to reduce aldehydes and ketones to alkanes; preferred when acid-sensitive groups are present.

Hofmann Elimination

An elimination reaction using $CH_3I$ (excess) followed by $Ag_2O / H_2O$ and heat to form the least substituted alkene from an amine.

Hell-Volhard-Zelinsky (HVZ) Reaction

A reaction using $PBr_3 / Br_2$ followed by $H_2O$ to achieve $ext{alpha}$-bromination of carboxylic acids.

Tollen's Reagent

A solution of $Ag(NH_3)_2^+ OH^-$ used to oxidize aldehydes to carboxylic acids, characterized by the formation of a silver mirror.

Hunsdiecker Reaction

Converts carboxylic acids into alkyl halides with one less carbon using $HgO$, $Ag_2O$, or $Pb(OAc)_4$ followed by $Br_2 / CCl_4$ and heat.

Wittig Reaction

The reaction of an aldehyde or ketone with a phosphorous ylide to form an alkene, where the trans-alkene is typically the major product for stability.

Stork Enamine Synthesis

A three-step process involving the formation of an enamine from a ketone or aldehyde, followed by alkylation with an alkyl halide, and ending with hydrolysis to restore the carbonyl.

Pinacol-Pinacolone Rearrangement

The acid-catalyzed conversion of a vicinal diol to a ketone via a methyl shift and dehydration.