PRESENTED BY:

Beverly Bayo

Mark Erick Zoleta

IV-BSCT

organic compounds and functional groups

that contain a basic nitrogen atom with a

lone pair.

derivatives of ammonia

one or more hydrogen atoms have been

replaced by a substituent such as an alkyl or

aryl group

A. Alkaloids

NICOTINE

coniine (from hemlock)

B. Phenylethylamines

C. Excitatory Neurotransmitters

Lysergic acid diethylamide

DopamineSerotonin

Acetylcholine

Aliphatic amines no aromatic ring attached directly to the nitrogen

atom

Aromatic amines have the nitrogen atom connected to an aromatic

ring as in the various anilines

Primary amines

Secondary amines

Tertiary amines

Cyclic amines

one of three hydrogen atoms in ammonia is

replaced by an alkyl or aromatic.

two organic substituents (alkyl, aryl or both)

bound to N together with one hydrogen (or

no hydrogen if one of the substituent bonds

is double).

all three hydrogen atoms are replaced by

organic substituents.

either secondary or tertiary amines

Chlorpheniramine

A. Primary Amines

1. IUPAC Name: Find longest chain and

replace –e ending with –

amine.

2. Common Name: Name alkyl group

attached to N and add

amine.

CH3CH2CH2CH2NH2

1-butanamine

butylamine

B. 2° & 3° Amines with Identical Substituents

B. 2° & 3° Amines with Different Substituents

1. Find longest chain or largest ring.

2. Name other groups in alphabetical order,

with –N prefix for each.

B. 2° & 3° Amines with Different Substituents

1. Find longest chain or largest ring.

2. Name other groups in alphabetical order,

with –N prefix for each.

A. Nucleophilic Substitution

1. Direct Nucleophilic Substitution

•RX limited to methyl

and 1° alkyl halides.

• Complicated by

polyalkylation.

Useful for preparing 1° amines and

quaternary ammonium salts

2. Alkylation of Ammonia

1°, 2°, and 3° amines all have similar reactivity; the initially

formed monoalkylation product can undergo further reaction

to yield a mixture of alkylated products

2. Gabriel Synthesis of 1° Amines

transforms primary alkyl halides into primary amines.

Traditionally, the reaction uses potassium phthalimide.

B. Reduction of Nitrogen-containing Functional Groups

C. Reductive Amination

Examples:

The Hoffmann Elimination

1° amine react with excess methyl iodide yield

quarternary (4°) ammonium salts. E2 elimination

of the resulting trimethyl ammonium group to give

an alkene.

PRESENTED BY:

Beverly Bayo

Mark Erick Zoleta

IV-BSCT