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Chapter 10

Amines are nitrogen-containing compounds derived from ammonia, classified as primary, secondary, or tertiary based on hydrogen replacement. They can be further categorized into aliphatic and aromatic amines, with physical properties including polarity and hydrogen bonding capabilities. Amines act as weak bases and nucleophiles, reacting with acids to form water-soluble salts and participating in nucleophilic substitution reactions.

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29 views20 pages

Chapter 10

Amines are nitrogen-containing compounds derived from ammonia, classified as primary, secondary, or tertiary based on hydrogen replacement. They can be further categorized into aliphatic and aromatic amines, with physical properties including polarity and hydrogen bonding capabilities. Amines act as weak bases and nucleophiles, reacting with acids to form water-soluble salts and participating in nucleophilic substitution reactions.

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Chapter 10- Amines

• Nitrogen is the fourth most common element in organic compounds.


• The most important chemical properties of amines are their basicity and their
nucleophilicity.
Amines are derivatives of ammonia (NH3) in which one or more hydrogens are replaced by
alkyl or aryl groups. Amines are classified as primary (1°), secondary (2°), or tertiary (3°),
depending on the number of hydrogen atoms of ammonia that are replaced by alkyl or aryl
groups

• Amines are further divided into aliphatic amines and aromatic amines.
• aliphatic amine, all the carbons bonded directly to nitrogen are derived from alkyl groups
• aromatic amine, one or more of the groups bonded directly to nitrogen are aryl groups.
• Heterocyclic amine An amine in which nitrogen is one of the atoms of a ring. It can be
either aromatic or aliphatic.
• Heterocyclic aromatic amine An amine in which nitrogen is one of the atoms of an aromatic
ring.
• Alkaloids are basic nitrogen-containing compounds of plant origin

(a) A secondary (2°) heterocyclic aliphatic amine. (b) One tertiary (3°) heterocyclic aliphatic
amine and one heterocyclic aromatic amine. (c) A tertiary (3°) heterocyclic aliphatic amine.
Systematic Names
Systematic names for aliphatic amines are derived just as they are for alcohols. The suffix -e
of the parent alkane is dropped and is replaced by -amine; that is, they are named alkanamines
Secondary and tertiary amines are commonly named as N-substituted primary amines.
For unsymmetrical amines, the largest group is taken as the parent amine; then the smaller
group or groups bonded to nitrogen are named, and their location is indicated by the
prefix N (indicating that they are bonded to nitrogen):
• NH2 group has one of the lowest priorities

B. Common Names Common: names for most aliphatic amines are named as alkylamines

Example: 10.3
• When four atoms or groups of atoms are bonded to a nitrogen atom, we name the
compound as a salt of the corresponding amine. We replace the ending -amine (or
aniline, pyridine, or the like) by -ammonium (or anilinium, pyridinium, or the like)
and add the name of the anion (chloride, acetate, and so on).
• Compounds containing such ions have properties characteristic of salts, such as
increased water solubility, high melting points, and high boiling points.

Physical Properties of Amine


Amines are polar compounds, and both primary and secondary amines form intermolecular
hydrogen bonds
An N-H----N hydrogen bond is weaker than an O-H----O hydrogen bond, because the difference
in electronegativity between nitrogen and hydrogen (3.0 - 2.1 = 0.9 ) is less than that between
oxygen and hydrogen (3.5 - 2.1 = 1.4 ).

All classes of amines form hydrogen


bonds with water and are more soluble
in water than are hydrocarbons of
comparable molecular weight. Most
low-molecular-weight amines are
completely soluble in water (Table
10.1). Higher-molecular-weight amines
are only moderately soluble or
insoluble.
Both molecules can participate in hydrogen
bonding. However, the t-butyl group is larger and
bulkier, making it more difficult for the molecules
of t-butylamine to hydrogen bond to each other.
Acid–Base Properties of Amines
• Like ammonia, all amines are weak bases, and aqueous solutions of amines are basic

Basicity of amines can be expressed by the acid ionization constant of the corresponding conjugate
acid
because of the resonance interaction of the unshared pair on nitrogen with the pi system of the
aromatic ring. Because no such resonance interaction is possible for an alkylamine, the electron
pair on its nitrogen is more available for reaction with an acid:
Reactions of Amines with Acids
Amines, whether soluble or insoluble in water, react quantitatively with strong acids to form
water-soluble salts
This reaction is used in extraction technique to separate
amines from other organic compounds
Arylamines Synthesize
1. By hydrogenation of nitrobenzene

This method has the potential disadvantage that other susceptible groups, such as a carbon–
carbon double bond, and the carbonyl group of an aldehyde or ketone, may also be reduced

2- nitro group can be reduced to a primary amino group by a metal (Fe, Zn and Sn) in acid:
Amines act as nucleophile
Amines are moderate nucleophiles, they should undergo nucleophilic substitution reactions with
haloalkanes and other compounds containing a good leaving group
No further substitution reactions

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