o recognize the amine and amide functional groups • Learn the Nitrogen-Containing Functional Groups • Nitrogen is in Draw structural formulas for the following molecules:
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Chapter 6 Amines and Amides - Angelo State University
o recognize the amine and amide functional groups • Learn the Nitrogen-Containing Functional Groups • Nitrogen is in Draw structural formulas for the following molecules:
PHYSICOCHEMICAL PROPERTIES OF ORGANIC MEDICINAL
Cité 25 fois — Most importantly, amides are characterized by a "conjugated system" in which the NBEs of nitrogen can delocalized into the adjacent carbonyl (C=O) group
Unit One Part 2: naming and functional groups
nal group Structure Suffix Prefix General form acid R OH O –oic acid –carboxylic acid
In this handout, all of our functional groups are presented as
- try to draw 3D structures in a zig-zag shape C R C R H H H H C C C NH2 Br Functional groups 1 carboxylic acid 2 amide 3 bromo 4 alkene 5 amine 6 nitrile c
Drug Design: Functional groups / Pharmacological - UiO
ructure Activity Relationships Acetylcholine agonists: Identification of acidic / basic functional groups Amide 6 2 - 3 Ex monofuctional comp methanol - pentanol/hexanol
Structure - Activity Relationships
Cité 3 fois — which functional groups are important for binding and for binding and activity • 1o and 2o amines are converted to 2o and 3o amides respectively • amides cannot
Functional Groups
nal Groups functional group: an atom, or group of atoms (with specific connectivity), exhibiting
Chapter 17 An Introduction to Organic Chemistry, Biochemistry
r percentage of amide functional groups in nylon molecules' structures leads to stronger hydrogen
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Chapter 6 Amines and Amides
Mr. Kevin A. Boudreaux
Angelo State University
CHEM 2353 Fundamentals of Organic Chemistry
Organic and Biochemistry for Today (Seager & Slabaugh) www.angelo.edu/faculty/kboudreaChapter Objectives:
•Learn to recognize the amine and amide functional groups. •Learn the IUPAC system for naming amines and amides. •Learn the important physical properties of the amines and amides. •Learn the major chemical reactions of amines and amides, and learn how to predict the products of amide synthesis and hydrolysis reactions. •Learn some of the important properties of condensation polymers, especially the polyamides.Chapter 6
Amines and Amides
2Nitrogen-Containing Functional Groups
• Nitrogen is in Group V of the periodic table, and in most of its compounds, it has three single bonds and one lone pair:
• In this chapter, we will take a look at two functional groups which contain nitrogen atoms connected to carbons: the amines and the amides.
RCO N R"R' Amide NRR'' R' Amine NChapter 6 Amines and Amides
3Classification and
Nomenclature of Amines
4Amines
• Amines and amides are abundant in nature. They are a major component of proteins and enzymes, nucleic acids, alkaloid drugs, etc. (Alkaloids are N-containing, weakly basic organic compounds; thousands of these substances are known.)
•Aminesare organic derivatives of ammonia, NH 3 , in which one or more of the three H's is replaced by a carbon group.• Amines are classified as primary(1°), secondary (2°), or tertiary(3°), depending on how many carbon groups are connected to the nitrogen atom.
NRR'' R'3° Amine
NRH H1° Amine
NRH R'2° Amine
NHH HAmmonia
Chapter 6 Amines and Amides
5Examples: Classifying Amines
• Classify the following amines as primary (1°), secondary (2°), or tertiary (3°). NCH 3 CH 2 CH 2 H H NCH 3 CH 3 CH 3 CH 3 CH 2 CHCH 3 NH 2 NCH 3 CH 2 H CH 3NH N 6Nomenclature of Amines
•Simple 1°, 2°, and 3° amines: common (trivial) names are obtained by alphabetically arranging the names of the alkyl substituents on the nitrogen and adding the suffix -amine(e.g., ethylmethylamine).
•Amines in the IUPAC system: the "e" ending of the alkane name for the longest chain is replaced with -amine. The amine group is located by the position number. Groups that are attached to the nitrogen atom are located using "N" as the position number. More complex primary amines are named with - NH
2 as the aminosubstituent.•Aromatic amines: named as derivatives of the parent compound aniline. Substituents attached to the nitrogen are indicated by using "N-" as the location number.
NH 2 anilineChapter 6 Amines and Amides
7Examples: Nomenclature of Amines
• Provide common names for the following 2° and 3°amines; for 1° amines, provide common and/or IUPAC names where possible.
CH 3 NH 2 CH 3 NCH 3 H CH 3 CH 2 CH 2 NH 2 CH 3 NCH 2 CH 3 H 8Examples: Nomenclature of Amines
• Provide common names for the following 2° and 3°amines; for 1° amines, provide common and/or IUPAC names where possible.
CH 3 CH 2 CH 2 CHCH 3 NH 2 CH 3 NCH 3 CH 3 CH 3 CHCH 2 CH 2 NH 2 NH 2 CH 3 CH 2 CH 2 CHCH 3 NHCH 3Chapter 6 Amines and Amides
9Examples: Nomenclature of Amines
• Provide common names for the following 2° and 3°amines; for 1° amines, provide common and/or IUPAC names where possible.
CH 3 CCH 2 CH 2 CH 2 CHCH 3 ONH 2 OH NH 2 10Examples: Nomenclature of Amines
• Provide names for the following aromatic amines. NCH 3 CH 3 NCH 3 CH 2 CH 3 NH CH 3 NH 2 CH 3Chapter 6 Amines and Amides
11Examples: Nomenclature of Amines
• Provide names for the following aromatic amines. NCH 3 CH 3 CH 3 NCH 3 H CH 2 CH 3 NCH 3 CH 3 CH 3 CH 3 CH 2 12Examples: Nomenclature of Amines
• Draw structural formulas for the following molecules: - ethylisopropylamine - tert-butylamine - 2-pentanamineChapter 6 Amines and Amides
13Examples: Nomenclature of Amines
• Draw structural formulas for the following molecules: - N-methyl-2-propanamine - 1,6-diaminohexane - 3-amino-1-propanol 14Examples: Nomenclature of Amines
• Draw structural formulas for the following molecules: - N-methyl-2-chloroaniline - N,3-diethylaniline - N,N-dimethylanilineChapter 6 Amines and Amides
15Physical Properties of
Amines
16Physical Properties of Amines: H-Bonding
• 1° and 2° amines can hydrogen bond to each other: NCH 3 CH 3 H CH 3 CH 3 H NNCH 3 CH 3 H NCH 3 CH 3 CH 3 CH 3 CH 3 CH 3 NCH 3 NCH 3 CH 3 XX • 3° amines cannot hydrogen bond to each other: NCH 3 HH CH 3 HH NNCH 3 H HChapter 6 Amines and Amides
17Physical Properties of Amines: Boiling Points
• Nitrogen is less electronegative than oxygen, so the N - H bond is not quite as polar as the O - H bond.
- Hydrogen bonds from N - H's are not as strong as those resulting from O - H's.- Hydrogen bonding between 1° and 2° amines is not as strong as those found in alcohols or carboxylic acids.
• 1° and 2° amines have lower boiling points than alcohols of similar molecular weight.• 3° amines, since they do not hydrogen bond to each other, have boiling points similar to hydrocarbons of the same molecular weight.
18