chem-103: basic organic chemistrystaff.du.edu.eg/upfilestaff/447/courses/8447_1365850776... ·...
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![Page 1: CHEM-103: BASIC ORGANIC CHEMISTRYstaff.du.edu.eg/upfilestaff/447/courses/8447_1365850776... · 2013. 4. 13. · LECTURE 10 Dr Ali El-Agamey CHEM-103: BASIC ORGANIC CHEMISTRY DAMIETTA](https://reader036.vdocuments.us/reader036/viewer/2022081411/60a95251e8a53206f2533ccf/html5/thumbnails/1.jpg)
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
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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)
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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.
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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
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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.
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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.
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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.
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Chapter 19 ٢١
Ammonium Salts
• Ionic solids with high melting points.
• Soluble in water.
• No fishy odor.
٢٢
(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)