LECTURE 10
Dr Ali El-Agamey
CHEM-103:
BASIC ORGANIC CHEMISTRY
DAMIETTA UNIVERSITY
2010, Prentice Hall
Organic Chemistry, 7th EditionL. G. Wade, Jr.
Carboxylic Acids and their Derivatives
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Preparations
Same carbon number
Higher carbon number
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Reactivity
Least reactive
Most reactive
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Reactions
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Reactions
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No reaction
Reactions
2010, Prentice Hall
Organic Chemistry, 7th EditionL. G. Wade, Jr.
Amines
Chapter 19 ٩
Classes of Amines
• Primary (1): Has one alkyl group bonded to the nitrogen (RNH2).
• Secondary (2): Has two alkyl groups bonded to the nitrogen (R2NH).
• Tertiary (3): Has three alkyl groups bonded to the nitrogen (R3N).
• Quaternary (4): Has four alkyl groups bonded to the nitrogen and the nitrogen bears a positive charge(R4N
+).
Chapter 19 ١٠
Examples of Amines
NH2 N
H
N
CH3
Primary(1º)
Secondary(2º)
Tertiary(3º)
Chapter 19١١
Common Names
• For common names, name the alkyl groups attached to the nitrogen, followed by the suffix -amine.
Chapter 19 ١٢
Amine as Substituent
Common: -Aminobutyric acid
• In complicated structures, -NH2 group is called theamino group. Also, the largest or most complicated alkyl group is taken to be the parent name.
Chapter 19 ١٣
IUPAC Names• Name is based on longest carbon chain.• -e of alkane is replaced with -amine.• Give a number to show the position of the amino
group along the chain• Substituents on nitrogen have N- prefix.
Write the IUPAC name of the following compounds
3-bromo-1-pentanamine N,N-dimethyl-3-hexanamine
NH2CH2CH2CHCH2CH3
Br
CH3CH2CHCH2CH2CH3
N(CH3)2
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IUPAC Names
Write the IUPAC name of the following compounds
acid > ester > amide > nitrile > aldehyde > ketone > alcohol > amine > alkene > alkyne
Homework: Write the IUPAC name for each of the following compound
Chapter 19 ١٦
Structure of Amines
• Nitrogen is sp3 hybridized with a lone pair of electrons.
• The angle is less than 109.5º.
Chapter 19١٧
Boiling Points
• Tertiary amines are hydrogen bond acceptors only (they do not have any hydrogens), so they have lower boiling points than primary and secondary amines.
• N—H less polar than O—H.• Weaker hydrogen bonds, so amines will have a
lower boiling point than the corresponding alcohol.
Chapter 19 ١٨
Solubility and Odor
• Small amines (< 6 Cs) are soluble in water.
• All amines accept hydrogen bonds from water and alcohol.
• Most amines smell like rotting fish.
Chapter 19 ١٩
Reactivity of Amines
Chapter 19 ٢٠
Basicity of Amines
• Lone pair of electrons on nitrogen can accept a proton from an acid.
• Aqueous solutions are basic to litmus.
• Alkyl amines are usually stronger basesthan ammonia.
Chapter 19 ٢١
Ammonium Salts
• Ionic solids with high melting points.
• Soluble in water.
• No fishy odor.
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(1) Hofmann degradation of amides
Preparations
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Preparations
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Reductive Amination
Reductive Amination: is the conversion of an aldehyde or ketone to an amine via an imine.
Imine
Preparations
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Homework: Complete the following scheme
(1) (2) (3) (4)
(5)
(6) (7)
(8)
(9) (10) (11)