Amines study sheet for Midterm II

Amines study sheet for Midterm II - Synthesis of Amines...

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Unformatted text preview: Synthesis of Amines Alkyl Halide & Ammonia (Amine) MEI. :NHSI Mfiffi III-H lon'1 H MIF_H But! ! H I‘ll-H :NH3 H M" @ u—H NH4 H MEI. H —I- | Mfi_H I|i H Even if you use an excess of annnonia, you still get a large amount dialkylation and even some tri- and tetraalkylation. Can be used for secondary and tertiary amines and quaternary ammonium salts. Synthesis ef Amines Rednetien ef Nitriles (enly 1° Amines) \ABI‘ ma. V‘CN 1) LjA1H4 2) H30 WNHE Always get a primal}.F amine with 1 more carbon atom. Synthesis ef Amines Rednetien ef Amides (1°, 2°, 3°Amines) CH NH L i _..-CH3 11‘ H Preparatifln 0f Arylamines NO2 NH2 H2, Pt Ethanol N01 1. Fe, HCl NH2 2. NaOH, H20. 0 N01 1. 311012, HCl NH: 2. NaOH, H20 Acylatiun 0f Amines i& i H3C C1 pyfidine H30 NH2 ji —a..CH3I‘IH2 i CH M (:1 mam H30 If 3 H i O H3C (31 @111. i ,CHg pyridine HSC III CH3 (Could also use anhydride) Brflminatifln 0f Anilines NH2 NHE Br Br BITE —I- H20 Br Activation Effect is so strong, can't mono bmminate directly, but... NH; Hm (CH3C0)20 Pyridine CH3 CH3 1131': J: H“. ,H M N H N Br Br NaOH H30 CH3 CH3 Diazanium Salts fram Arylamines 6) NH: NaNO2 N2 —I- H2804 00 Benzenediazonimn ion 9 : NI’N Reaaonable life time at 0° due to resonance stabilization e I + N2 Instantly. Good way to make Carbocations. Sandmeyer Reaction of Diaznnium Salts C1 39 Other Substitutinn Reactinns 0f Diazflnium Salts (-3 COT“: (2” GB 1 N2 H30+ OH —- ...
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This note was uploaded on 12/16/2008 for the course CHEM 140B taught by Professor Nefzi during the Spring '06 term at UCSD.

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Amines study sheet for Midterm II - Synthesis of Amines...

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