Organic Chemistry I: Substitution Reactions

These flashcards cover key vocabulary terms and concepts from Organic Chemistry I, specifically related to substitution reactions.

Nucleophile

A species that supplies an electron pair.

Electrophile

A species that seeks an electron pair.

Alkyl Halide

A compound containing a halogen covalently bonded to an sp3 hybridized carbon, symbolized as RX.

Vinyl Halide

A compound containing a halogen bonded to an sp2 hybridized carbon.

Aryl Halide

A compound containing a halogen bonded to a benzene ring, symbolized as ArX.

Polar Bonds

Bonds where C–X exhibits a slight positive charge on carbon and a slight negative charge on halogen.

Polyhaloalkanes

Compounds where all hydrogens are replaced by halogens, often used as solvents.

Nucleophilic Substitution

A reaction where a nucleophile replaces a leaving group in a molecule.

SN2 Mechanism

A unimolecular nucleophilic substitution mechanism involving a single transition state.

Walden Inversion

The inversion of configuration at a stereogenic center due to the backside attack of a nucleophile.

Carbocation

A species in which a carbon atom has only six electrons in its valence shell and bears a positive charge.

Hyperconjugation

A stabilizing interaction that results from the overlap of a σ-bond orbital with an empty p-orbital of the cation.

Inductive Effect

The donation of electron density along sigma bonds, stabilizing a carbocation.

Weak Bases

Species that make excellent leaving groups in nucleophilic substitution reactions.

Racemization

The formation of a racemic mixture, typically occurring in SN1 reactions due to nucleophilic attack on both sides of a planar carbocation.

Steric Hindrance

The prevention of reaction due to the size of substituents surrounding the reactive site.

Solvent Effects

The influence of solvent properties on the reactivity and mechanism of nucleophilic substitution reactions.