Organic Chemistry - Nucleophilic Substitution Reactions

This set of flashcards covers key vocabulary terms and concepts related to nucleophilic substitution reactions in organic chemistry, including definitions and mechanisms.

Alkyl Halides

Organic molecules containing a halogen atom bonded to an sp3 hybridized carbon atom.

SN1 Reaction

A nucleophilic substitution mechanism involving two steps and the formation of a carbocation intermediate.

SN2 Reaction

A bimolecular nucleophilic substitution that occurs in one step, involving simultaneous bond making and breaking.

Leaving Group

An atom or group that departs with an electron pair during a nucleophilic substitution reaction.

Nucleophile

A species that donates an electron pair to form a chemical bond in reaction.

Carbocation

A positively charged carbon species, often formed as an intermediate in SN1 reactions.

Steric Hindrance

The decrease in reaction rate due to the presence of bulky groups that hinder access to the reactive site.

Transition State

A high-energy state during a chemical reaction where bonds are partially broken and formed.

Electrophile

A species that accepts an electron pair in a chemical reaction.

Solvent Effects

The influence of solvent polarity on the nucleophilicity and reaction mechanism of nucleophilic substitutions.

Protic Solvents

Solvents that can form hydrogen bonds and stabilize ions.

Aprotic Solvents

Solvents that cannot form hydrogen bonds, affecting nucleophilicity differently.

Reactivity Trend

In SN1 reactions, reactivity increases with the number of alkyl substituents on the carbocation.

Racemization

The formation of a racemic mixture of enantiomers due to equal probability of nucleophilic attack from either side of a planar carbocation.

Hammond Postulate

States that the transition state resembles the structure of the species (reactant or product) to which it is closer in energy.