Organic Chemistry

Chapter 10: Nitrogen & Phosphorous Compounds

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Amino acids contain an ____.

The α -carbon, with its four different groups, is a c____enter.

____ does not have a stereogenic center.

All naturally occurring amino acids in eukaryotes are optically ____-isomers.

____-amino acids have (S) configurations

L-amino acids have (____) configurations

____ has (R) configuration.

Cysteine has (____) configuration.

Amino acids, with their acidic ____ group, are amphoteric molecules.

Amino acids, with their acidic carboxyl group and basic amino group, are ____ molecules.

Amino acids, with their ____ amino group, are amphoteric molecules.

On amino acids, amino groups can take on a positive charge by being ____.

On amino acids, ____ groups can take on a positive charge by being protonated.

On amino acids, amino groups can take on a ____ charge by being protonated.

On amino acids, ____ groups can take on a negative charge by being deprotonated.

On amino acids, carboxyl groups can take on a negative charge by being ____.

On amino acids, carboxyl groups can take on a ____ charge by being deprotonated.

When an amino acid is put into solution, it will take on both positive and negative charges, forming a ____

In ____ solutions, the amino acid can become fully deprotonated.

In basic solutions, the amino acid can become ____.

In ____ solutions, the amino acid can become fully protonated.

In acidic solutions, the amino acid can become ____.

Proteogenic amino acids are grouped into five categories: ____.

Aromatic amino acids include ____.

____ amino acids tend to have terminal groups containing oxygen, nitrogen, or sulfur.

Polar amino acids tend to have terminal groups containing ____.

____ amino acids are all hydrophilic amino acids.

Nonpolar nonaromatic amino acids tend to have side chains that are ____.

____ amino acids are also hydrophobic and tend to be sequestered in the interior of proteins.

Nonpolar amino acids are also ____ of proteins.

Proline is a ____ group.

____ is a cyclic nonpolar (not aromatic tho) amino acid with a secondary amine group.

Amino acids undergo condensation reactions to form ____.

Amino acids undergo ____ reactions to form peptide bonds.

Hydrolysis of the peptide bond, is catalyzed by ____.

Amides have ____ resonance structures.

Rotation is limited around the peptide bond because r____.

In the Strecker synthesis, one starts with ____.

In the ____, one starts with an aldehyde, ammonium chloride ( NH 4 Cl), and potassium cyanide (KCN).

Strecker Synthesis: Step #1: ____. Step #2: Ammonia can attack the carbonyl carbon, forming an imine . Step #3 : The imine carbon is also s…

Strecker Synthesis: Step #1: The carbonyl oxygen is protonated, increasing the electrophilicity of the carbonyl carbon. Step #2: ____. Step…

Strecker Synthesis: Step #1: The carbonyl oxygen is protonated, increasing the electrophilicity of the carbonyl carbon. Step #2: Ammonia ca…

Strecker Synthesis: Step #1: The carbonyl oxygen is protonated, increasing the electrophilicity of the carbonyl carbon. Step #2: Ammonia ca…

The last step of Strecker synthesis can be performed in a____.

The ____ synthesis uses a resonance-stabilized nitrogen nucleophile to synthesize 1° amines via nucleophilic substitution.

The Gabriel synthesis uses a ____.

An amino acid is generated from phthalimide and diethyl bromomalonate, using ____.

An amino acid is generated from ____, using two S N 2 reactions, hydrolysis, and decarboxylation.

Gabriel Synthesis: Step #1: ____. Step #2: Add a base to deprotonate the alkylated imide we formed, allowing it to act as a nucleophile. St…

Gabriel Synthesis: Step #1: Potassium phthalimide is reacted with diethyl bromomalonate in an SN 2 reaction to form a substitution product…

Gabriel Synthesis: Step #1: Potassium phthalimide is reacted with diethyl bromomalonate in an SN 2 reaction to form a substitution product…

Gabriel Synthesis: Step #1: Potassium phthalimide is reacted with diethyl bromomalonate in an SN 2 reaction to form a substitution product…

Gabriel Synthesis: Step #1: Potassium phthalimide is reacted with diethyl bromomalonate in an SN 2 reaction to form a substitution product…

Both the ____ synthesis methods result in a racemic mixture of amino acids.

Both the Strecker and Gabriel synthesis methods result in a ____ mixture of amino acids.

The Gabriel synthesis begins with phthalimide, one of a group of compounds called ____.

The N-H bond of an imide is especially acidic because ____.

The N-H bond of an imide is especially ____ because the resulting anion is resonance stabilized by the two flanking carbonyl groups.

In a biochemical context, phosphoric acid is sometimes referred to as a ____ .

In a biochemical context, ____ is sometimes referred to as a phosphate group or inorganic phosphate .

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