Lecture 7 - Amines and Derivatives

Lecture 7 - Amines and Derivatives - BME 201, Amines and...

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1 BME 201, Amines and Derivatives Suggested problems and review material: Vollhardt 6 th Ed., Chapter 21, Problems: 27, 28, 35, 36, 37, 63, 65, Chemical highlight 21-1 Todays lecture is based on Vollhardt, selected materials from chapters 21 ( amines and derivatives ) as well as selected handouts. Handouts may have marked chapter numbers and page numbers for suggested reading. You will find it easier to do the suggested problems and pass future quizzes and exams if you go over the reading prior to attempting to solve the suggested problems.
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2 Amines and Their Derivatives What drug is this ? Prozac: fluoxetin; 9R,S)-N-methyl-3-(4-trifluoromethylphenoxy)-3- phenyl-1-propanamine) Nitrogen
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3 How to activate Nitrogen N 2 ? How to break a N 2 triple bond? The nodules in the root system of the soybean are the sites of nitrogen reduction by Rhizobium bacteria
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4 Naming the Amines 21-1 Amines are related to ammonia in the same sense that ethers and alcohols are related to water. In the amines, the number of –R groups on the nitrogen atom defines the designation of primary, secondary and tertiary. Aliphatic amines are named as alkanamines according to Chem Abstracts. The name of the alkane stem is modified by replacing the ending – e with –amine.
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5 The position of the functional group is indicated, as in alcohols, by prefixing the carbon atom to which it is attached. Substances containing two amine functions are called diamines:
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6 Aromatic amines (or anilines) are called benzenamines. For secondary and tertiary amines, the largest alkyl substituent on nitrogen is chosen as the alkanamine stem. Other groups are named using N-, followed by the name of the additional substituent(s).
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7 An alternate naming convention is to treat the amino- functional group as a substituent of the alkane stem.
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8 Structural and Physical Properties of Amines 21-2 The alkanamine molecule is tetrahedral. The nitrogen orbitals in amines are very nearly sp 3 hybridized. The term pyramidal is often used to describe the geometry of the nitrogen atom and its three substituents.
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9 When an amine bears three different substituents (plus the lone pair of electrons), it has the potential to be optically active : At ordinary temperatures amines are not optically active, however because of a rapid isomerization process called inversion .
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10 The transition state for the inversion of an amine has been found to be between 5 and 7 kcal mol -1 for ordinary small amines. It is therefore impossible to keep an enantiomerically pure, simple
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Lecture 7 - Amines and Derivatives - BME 201, Amines and...

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