Organic Chemistry

Chapter 4: Analyzing Organic Reactions

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In an acid–base reaction, an acid and a base react, resulting in the formation of the ____ of the base.

An acid–base reaction will only proceed if the products that will be formed are ____

A Lewis acid is defined as ____ .

A ____ is defined as an electron acceptor .

A Lewis base is defined as ____ .

A ____ is defined as an electron donor .

Lewis acids also tend to be ____.

Lewis acids have ____ into which they can accept an electron pair.

Lewis bases also tend to be ____.

When Lewis acids and bases interact, they form ____ bonds .

Coordinate covalent bonds are covalent bonds in which ____

____ are covalent bonds in which both electrons in the bond came from the same starting atom.

In the Brønsted–Lowry definition, ____ is a species that can donate a proton (H + ).

In the Brønsted–Lowry definition, an acid is a species that can ____ a proton (H + ).

In the ____ definition, an acid is a species that can donate a proton (H + ).

In the Brønsted–Lowry definition, ____ is a species that can accept a proton (H + ).

In the Brønsted–Lowry definition, a base is a species that can a____ proton (H + ).

Some molecules, like water, have the ability to act as either Brønsted–Lowry acids or bases, making them ____.

The ____, measures the strength of an acid in solution.

In the dissociation of an acid HA (HA ⇌ H + + A – ), the equilibrium constant is given by:____

The p K a can be calculated as:

More acidic molecules will have a ____ p K a .

More basic molecules will have a ____ p K a .

Weak organic acids often have p K a values between ____.

Acids with a p K a ____ are considered strong acids.

The more electronegative an atom, the ____ the acidity.

The nitrogen atom of an amine can form ____ bonds by donating a lone pair to a Lewis acid.

The nitrogen atom of an amine can form coordinate covalent bonds by donating a lone pair to a Lewis ____.

Nucleophiles are defined as “nucleus-loving” species with ____ that can form new bonds to electrophiles.

Nucleophile strength is based on ____.

____ strength is based on relative rates of reaction with a common electrophile.

Base strength is based on ____.

____ strength is based on the equilibrium position of a reaction.

Nucleophile strength is a ____ property.

____ strength is a kinetic property.

Base strength is a ____ property.

____ strength is a thermodynamic property.

On Test Day, look for ____ with a minus sign or lone pair to identify most nucleophiles.

Nucleophilicity is determined by four major factors: 1. ____

Nucleophilicity ____ with increasing electron density (more negative charge).

Nucleophilicity increases with ____ negative charge).

Nucleophilicity decreases as electronegativity ____.

Nucleophilicity ____ as electronegativity increases.

Nucleophilicity decreases as electronegativity increases because ____.

Bulkier molecules are ____ nucleophilic.

____ solvents can hinder nucleophilicity by protonating the nucleophile or through hydrogen bonding.

In polar ____ solvents, nucleophilicity increases down the periodic table.

In polar protic solvents, nucleophilicity increases ____ the periodic table.

In polar aprotic solvents, nucleophilicity increases ____ the periodic table.

In polar ____ solvents, nucleophilicity increases up the periodic table.

In protic solvents, nucleophilicity decreases because ____.

In ____ solvents, nucleophilicity decreases because the protons in solution will be attracted to the nucleophile.

In aprotic solvents, nucleophilicity decreases because ____.

In ____ solvents, nucleophilicity decreases because there are no protons to get in the way of the attacking nucleophile.

We won’t use nonpolar solvents with nucleophillic reactions because ____.

Electrophiles are defined as “electron-loving” species with a ____ polarized atom.

Electrophile act like Lewis ____.

A greater degree of positive charge increases ____.

Better ____ make it more likely that a nucleophile-electrophile reaction will happen.

The conjugate base is always a better ____.

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