Secondary amine

Amines are derivatives of ammonia in which one or more of the hydrogens has been replaced by an alkyl or aryl group.

Reactions of amines are not a huge focus with the new MCAT. However, their solubility and acid-base properties are crucial. Additionally, it is important to get a handle on the nomenclature of heterocylic rings containing nitrogen, of which many are amines, such as indole, imidazole, and piperidine. While it would be uncharacteristic for the MCAT to penalize you on nomenclature, learning to recognize those forms has a way of making many of the complex molecules in biochemistry more coherent.

WikiPremed Resources

Reactions of Amines Images
Image gallery for study with links to larger teaching JPEGs for classroom presentation

Question Drill for Amines
Conceptual Vocabulary Self-Test

Basic Terms Crossword Puzzle

Basic Puzzle Solution

Learning Goals

Proficiency 

Understand the properties of amines as weak bases.

Be familiar with Amine mechanisms we have seen in other contexts including SN1 or SN2 Substitution with Alkyl Halides where an Amine is the nucleophile, the reaction of Amines as the nucleophile with Aldehydes and Ketones such as occurs in Reductive Amination, the the reaction of Amines with Carboxylic Acid Derivatives such as with Acyl Halides and in Hofmann Elimination.

Suggested Assignments

Review the basic terms for reactions of aldehydes & ketones using the question server. Complete the fundamental terms crossword puzzle. Here is the solution to the puzzle.

Read pg. 86 in ExamKrackers Chemistry. Perform practice items 49-56 on pp. 87-88 (practice items for aldehydes & ketones, alcohols, and amines).

Review the web resources for reactions of amines.

Conceptual Vocabulary for Amines

Amine
Amines are organic compounds and a type of functional group that contain nitrogen as the key atom, structurally resembling ammonia, but one or more hydrogen atoms is replaced by alkyl and aryl groups.
Quaternary ammonium cation
Quaternary ammonium cations, also known as quats, are positively charged polyatomic ions in which a nitrogen atom is bound to four alkyl groups.
Enamine
An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of a water molecule.
Isocyanide
An isocyanide is an organic compound in which nitrogen and carbon are connected through a triple bond with a positive charge on nitrogen and a negative charge on carbon.
Aniline
Aniline is the simplest aromatic amine, consisting of a phenyl group with a single amine substituent.
Reductive amination
Reductive amination is a chemical reaction which involves the conversion of an aldehyde or ketone to an amine.
Diazonium compound
Diazonium salts are a group of organic compounds in which an alkyl or aryl portion is bound to a functional group with two nitrogens, triple bonded, forming a cation.
Alkylimino-de-oxo-bisubstitution
Alkylimino-de-oxo-bisubstitution is acid catalyzed nucleophilic addition reaction of carbonyl compounds with amines to form imines.
Nitroso
Nitroso refers to a functional group in organic chemistry which has the general formula RNO. These compounds can be prepared by the reduction of nitro compounds or by the oxidation of hydroxylamines.
Hemiaminal
A hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom. These are intermediates in alkylimino-de-oxo-bisubstitution.
Schiff base
A Schiff base is a functional group that contains a carbon-nitrogen double bond with the nitrogen atom connected to an aryl or alkyl group, but not hydrogen.
Nitrous acid
Nitrous acid is a weak monobasic acid known only in solution and in the form of nitrite salts. It is used to make diazides from amines
Emde degradation
The Emde degradation is a method for the reduction of a quaternary ammonium cation to a tertiary amine with sodium amalgam.
Cope reaction
The Cope reaction is an elimination reaction of an amine oxide to form an alkene and a hydroxyl amine.
Advanced terms that may appear in context in MCAT passages
Zincke reaction
The Zincke reaction is an organic reaction in which a pyridine is transformed into a pyridinium salt by reaction with 2,4-dinitro-chlorobenzene and a primary amine.
Ugi reaction
The Ugi reaction is a multi-component reaction in organic chemistry involving a ketone or aldehyde, an amine, an isocyanide and a carboxylic acid to form a bis-amide.
Hofmann-Martius rearrangement
The Hofmann-Martius rearrangement in organic chemistry is a rearrangement reaction converting an N-alkylated aniline to the corresponding ortho and / or para aryl-alkylated aniline.
Mannich reaction
The Mannich reaction consists of the amino alkylation of an acidic proton placed next to a carbonyl functional group with formaldehyde and ammonia or any primary or secondary amine.
Eschweiler-Clarke reaction
The Eschweiler-Clarke reaction is a chemical reaction whereby a primary or secondary amine is methylated using excess formic acid and formaldehyde.
Forster-Decker method
The Forster-Decker method is a series of chemical reactions that transform a primary amine ultimately to a secondary amine. The first step is the formation of a Schiff base, followed by alkylation, and hydrolysis.