Organic Chemistry: Acids and Bases

Flashcards covering key concepts from Organic Chemistry Chapter 3 on Acids and Bases, including definitions, reaction mechanisms, factors affecting acidity, and different types of acids and bases.

The events that take place in a reaction in order for reactants to become products are called a __.

Reaction mechanism

__ are used to show the movement of electrons in a reaction mechanism, pointing from the source of electrons to the receiving atom.

Curved arrows

A __ indicates the movement of two electrons.

Full headed arrow

A __ indicates the movement of one electron.

Half headed arrow

An electron pair acceptor, often electron deficient, is known as a __.

Lewis acid

An electron pair donor is known as a __.

Lewis base

A positively charged carbon atom, typically sp^2 hybridized, formed via heterolysis, and acts as a Lewis acid, is a __.

Carbocation

A negatively charged carbon atom, typically sp^3 hybridized, formed via heterolysis, is a __.

Carbanion

An 'electron loving' species that seeks electrons, where all Lewis acids are also this type of species, is called an __.

Electrophile

A 'nucleus loving' species that donates electrons, and includes all Lewis bases, is a __.

Nucleophile

A measure of acid strength, where a smaller value indicates a stronger acid and a larger value indicates a weaker acid, is called __.

pKa

A __ yields a weaker conjugate base.

Stronger acid

A __ yields a stronger conjugate base.

Weaker acid

Acid-base reactions favor the formation of the and (most stable species), operating under equilibrium control.

weaker acid and weaker base

Acidity increases as the __ of the atom bearing the acidic hydrogen increases down a group.

atomic radius

More __ atoms stabilize negative charges better, leading to increased acidity within a given row.

electronegative

More __ in the orbital holding the electron pair of an anion leads to increased acidity (sp > sp^2 > sp^3).

s character

__ are electronic effects transmitted through bonds, such as electron-withdrawing groups increasing acidity by stabilizing the conjugate base.

Inductive effect

__ is the delocalization of electrons that stabilizes an anion, increasing the acidity of the parent compound.

Resonance stabilization

are more acidic than due to the resonance stabilization of the phenoxide ion.

Phenols, alcohols

__ are solvents that have H atoms bonded to highly electronegative atoms, forming H-bonds to stabilize the conjugate base.

Protic solvents

The __ states that in water, any base stronger than hydroxide can only be as strong as hydroxide, and any acid stronger than hydronium can only be as strong as hydronium.

Solvent leveling effect

__ are bases stronger than hydroxide, often generated from alcohols and strong bases like NaH.

Alkoxide bases

__ are extremely strong bases (e.g., R-Li) that act as a source of carbanions (R^-).

Alkyllithium bases

The process of incorporating a radioactive isotope (e.g., Deuterium, Tritium) into a molecule to trace its path in a reaction mechanism is called __.

Radiolabeling