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Amines

Amines. By Philippe Ferland and Kate Ridgley. What is an Amine?. Amines are organic derivatives of ammonia in which a trivalent nitrogen atom is bonded to one or more alkyl groups in a pyramidal shape or is found in a ring which is referred to as a “ heterocycle ”. . Cassifications.

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Amines

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  1. Amines By Philippe Ferland and Kate Ridgley

  2. What is an Amine? • Amines are organic derivatives of ammonia in which a trivalent nitrogen atom is bonded to one or more alkyl groups in a pyramidal shape or is found in a ring which is referred to as a “heterocycle”.

  3. Cassifications • 3 different types: primary, secondary, and tertiary. Primary Secondary Tertiary

  4. Naming • Common method involves finding the longest carbon chain then numbering the amines position before it and adding “amine” at the end. • The IUPAC method involve, finding the longest chain, then numbering the position of alkyl groups on the parent chain as well as placing them in alphabetical order, and finally numbering the position of the amine on the parent chain as well as using “amino” before the longest chain. Ex: NH3 NH3 NH2 Aminopropane Propylamine Methylaminomethane Dimethylamine 2-Aminobutane 2-Butylamine

  5. Hydrogen Bonding and Boiling Points • Like with alcohols, amines can undergo hydrogen bonding though their N-H bonds are much weaker then O-H bonds. This is why amines have a lower boiling point then alcohols of similar size. • The boiling point also depends on which classification the amine is part of. The difference between each of them is typically about 10 to 15 degrees with primary amines being the highest and tertiary amines being the lowest. Ex: Propylamine (primary) boils at 48ºC Ethylmethylamine (secondary) boils at 37ºC Trimethylamine (tertiary) boils at 3ºC

  6. Reactions Involving Amines • Amines can undergo alkylation reactions where an alkyl group from another compound is transferred a nitrogen atom or other amine. C2H5Br + NH3 C2H5NH2 + NH4Br • Another reaction is protonation. Because amines are Brønsted bases, and therefore nucleophiles, they can be mixed with an acid and exchange the nitrogen’s unbonded electrons for a hydrogen atom. C2H5NHCH3 + H2O C2H5NH2CH3 + OH

  7. Hinsburg Test • Used to identify what type of classification a specific amine is in. • Involves adding benzenesulfonylchloride to a 10% sodium hydroxide solution. Then adding the amine to be tested. • If a precipitate forms, then its either a primary or secondary amine, but if there is no reaction, then it is a tertiary amine. • To identify whether its a primary or secondary amine. The previous steps must be followed. After that, poor out as much of the 10% sodium hydroxide solution as possible then add pure sodium hydroxide. • If the precipitate disappears, then it is a primary amine, if not then it is a secondary amine.

  8. Examples of Chemicals • Putrescine • Cadaverine • Skatole • Dopamine • Norepinephrine • Epinephrine • Benzedrine • Mescaline • Pyridine • Aniline Chemistry.about.com Chemistry.about.com Chemistry.about.com chm.bris.ac.uk chm.bris.ac.uk chm.bris.ac.uk erowid.org erowid.org bmrb.wisc.edu Chemistry.about.com

  9. Every Day Uses • Everyday uses of amines involve: perfumes, medicine, herbicide, dyes, varnishes, and water repellant. More.ca apps.co.marion.or.us rexart.com

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