Ammonia Primary Secondary Tertiary Quarternary Ammonium Ion

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1 1 Chapter 19: Amines I. Introduction: Classification: NH 3 RNH 2 R 2 NH R 3 N R 4 N + Ammonia Primary Secondary Tertiary Quarternary Ammonium Ion Amines are a very common functional group in organic chemistry, and especially so for naturally occurring compounds.

2 II. Nomenclature 2 A. IUPAC Nomenclature 1) Find the longest carbon chain which contains the carbon attached to the NR 3 group. a) This is your parent b) Number nearest the NR 3 group 2) Add the suffix ##-parent anamine. OR an-##-amine 3) Add substituent names, with appropriate numbers, in front of the amine name. 4) Add the name of any other alkyl groups on the nitrogen in front, with an N- prefix. 5) For complicated carbon chains (with higher priority functional groups), name the NH 2 group as an amino substituent. Acids > ald > ket > alcohols > amines > B. Common Names Name all the carbon groups attached to nitrogen as alkyl groups, then add amine.

3 3 C. Special Common Names (MEMORIZE) NH NH N NH 2 NH D. Nomenclature: Ammonium Salts Nitrogen with four groups attached has a positive formal charge. These compounds are called ammonium ions, and they usually exist as salts with a corresponding anion. Nomenclature: 1) Name all of the carbon groups attached to the nitrogen as alkyl groups. 2) Add the name ammonium at the end. 3) Name the anion III. Structures of Amines

4 4 A. Resonance of Nitrogen compounds B. Stereochemistry Lone Pair Inversion at Nitrogen If the nitrogen of an amine has three different groups attached (plus the lone pair), it is a technically a stereocenter. However, nitrogen stereocenters do not hold their configuration. They racemize because the lone pair can invert through the nitrogen: C. Chirality Exceptions There are certain special cases where amines are chiral. CASE 1: Amines whose chirality stems from the presence of chiral carbon atoms. CASE 2: Quaternary ammonium salts with chiral nitrogen atoms. In this case, the nitrogen inversion is impossible since there are four substituents on the N, and no lone pair.

5 CASE 3: Steric restrictions. 5 IV. Physical Properties 1. Basicity of Amines A) Degree of Substitution of the Amine Carbon groups donate electrons to the nitrogen, which increases the electron density of the lone pair and increases the basicity of the amine The ammonium ion is stabilized by solvation. Tertiary ammonium ions are sterically hindered, which reduces solvation and makes them less stable. Therefore, tertiary amines are less basic than secondary amines.

6 6 B) Resonance Generally, makes amines bases than normal aliphatic amine because resonance ties up the lone pair. C) Hybridization Effects V. Reactions of Amines 1. Electrophilic Aromatic Substitution of Pyridine Pyridine is deactivated: The deactivation arises from the electron withdrawing effect of the nitrogen atom in the ring. EAS reactions require unusually harsh reaction conditions. o FC alkylations and acetylations fail.

7 Problems with EAS on pyridinde: 7 Examples of EAS reactions that do actually work on pyridine are shown below (note the very harsh conditions). 2. Nucleophilic Aromatic Substitution (NAS) Pyridine is strongly deactivated to EAS, but is activated toward attack by nucleophiles, i.e. NAS. Example

8 3. Alkylation of Amines Mechanism 8 4. Amines as Leaving Groups (Hoffman Elimination) Zaitsev vs.hofmann Product Least substituted product is called the Hoffman product. Most substituted alkene product is the Zaitsev product. Let s look at 2-butanamine

9 9 5. Reaction with Nitrous Acid The reaction of amines with nitrous acid (HNO 2 ) is a very useful synthetic reaction. Nitrous acid is unstable and needs to be generated in situ by reaction of sodium nitrite and hydrochloric acid. In very acidic media, nitrous acid can become deprotonated and lose water (acid catalyzed dehydration) and generate the nitrosonium ion, NO Reactions Involving Diazonium Salts A. Reaction with primary amines; B. Reaction with Secondary Amines (Diazonium Salts)

10 10 Summary of the Reactions of Arenediazonium Salts 1) Hydroxylation N N dil. H OH 2 SO 4, 2) Fluorination N N HBF F 4 3) Sandmeyer Reaction: Chlorination N N Cl CuCl 4) Sandmeyer Reaction: Bromination N N Br CuBr 5) Sandmeyer Reaction: Cyanation N N C N CuCN 6) Iodination N N I KI 7) Hydrogen Replacement N N H 3 PO 2 H 8) Diazonium Coupling N N N N + EDG EDG

11 7. Synthesis of Amines 11 A. Reductive Amination 1. Synthesis of Primary Amines 2. Synthesis of Secondary Amines

12 3. Synthesis of Tertiary Amines 12 The iminium salts are usually unstable, and so are reduced as they are formed by a reducing agent already in the reaction mixture. 8. Acylation - Reduction to Amines The amine is acylated with an acid chloride, and the amide produced thus has no desire to undergo further reaction (good). 9. Reduction of Nitro Compounds

13 10. Reduction of Azides and Nitriles (Primary Amines) 13 A. Azides The azide ion (N 3 - ) is a good nucleophile, and thus can displace leaving groups from primary and secondary alkyl halides and tosylates. The alkyl azides that are produced (explosive) are reduced to primary amines either by LiAlH 4 or catalytic reduction. B. Nitriles Cyanide ion (-CN) is also a good nucleophile, and the products it produces are called nitriles. (S N 2 reaction)

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