Amides Tyler E, Caroline K, Nikki W Period

Amides Tyler E, Caroline K, Nikki W Period

Amides Tyler E, Caroline K, Nikki W Period 1 Basic Structure Primary Amides- have an alkyl or aromatic group attached to an amirocarnonyl function. Secondary- An alkyl or aryl group attached to the nitrogen: RCONHR Tertiary- Two alkyl or aryl group attached to the nitrogen: RCONR2 The OH of the carboxyl group is replaced by the nitrogen holding any combination of H atoms (-NH2)

Characteristics Come from the carboxylic acids Contain the CONH group Very similar to esters except in excess of ammonia In water they change back to carboxylic acid and ammonia Non basic unlike amines Least reactive of neutral carboxylic descendants Most are solid at room temperature except methanimide

Melting point usually high Nomenclature The simplest way of naming amides is when nitrogen is bonded with two hydrogen atoms. Steps: -Start with the carboxylic acid then cross off the ic or oic acid and replace it with amide. Acetamic=Acetamide, Formaic=Formaide, Butanamic= Butanamide Secondary: Upper case N to designate the Alkyl group is on the nitrogen atom. Tertiary amides are named the same way Ex: N-methylpropanamide Mechanisms Similar to those of esters The mechanism for amide formation

proceeds via attack by the ammonia molecule on the carboxyl carbon of the acid. The alkoxide ion that form assists with the displacement of the chloride ion. Mechanisms Mechanism of the acid catalyzed : Starts with Oxygen, Ends with NH4 When aqueous solutions of carboxylic acids and amines are mixed, it is an acid-base reaction. To prepare an amide: react acyl chloride with an amine. Lots of amines are used to complete the reaction because they absorb the HCl that is given off.

Mechanisms This tertiary amides has lithium aluminum hydride and involves a hydride addition. The carbonyl oxygen is considered a better leaving group than the nitrogen group, so lithium trialkyl aluminate is released, and the reduction proceeds to yield the amine. The aluminate that was released generates an iminium ion which reacts to form another hydride ion. ***The decrease of primary and secondary amides

is similar to the tertiary amides. However, the amide is not the reactant , the conjugated base is. The strong base lithium aluminum hydride makes this formation. Examples

Ethanamide - CH3CONH2 Propanamide - C3H7NO Formamide - CH3NO Hexamide - C6H13NO Decanmide - C10H2NO Real World Importance The most common amide is the fiber known as nylon. In 1931, the American chemist, Wallace Hume Carothers, discovered a process that made one of the

first synthetic fibers. Adding adipic acid to hexamethylene diamine resulted with a strong, fiber-like product. He named it Nylon 66 which reflects the six carbon atoms in adipic acid and hexamethylene diamine molecules. Hiking and fishing gear would be very different without the use of nylon. Real World Importance Making amide bonds are limited because of the small amount of methods The processes are inefficient and can prove difficult to use when joining large strands or fragments. Researchers at the University of California have developed a process to prepare bonds under mild, aqueous, reagent-free conditions, with water and carbon dioxide as the only by-products. The reaction involves combining alpha-keotacids and Nalkylhydroxylamines in a highly chemoselective amide bond formation

process. Research has confirmed a high tolerance of this process to the presence of reactive functional groups including free amines, carboxylic acids, azides, and heterocycles. Experiments have demonstrated couplings that produced the desired amide in 50%-99% isolated yield without epimerization Uses the construction of complex organic molecules, including synthetic proteins; tandem ligation for complex biomolecule synthesis; the coupling of unprotected molecules template-directed peptide synthesis. *Questions* 1- What makes up a primary amide? A. Nitrogen and an aryl group B. Alkyl or aromatic group attached to an amiro-carnonyl function.* C. Nothing

D. Four or more alkayl groups 2- How do amides change in water? A. They dissolve B. The groups separate C. They change back to carbonyl acid and hydrogen D. They change back to carboxylic acid and ammonia* 3- What ion helps with the displacement of the chloride ion? A.Alkoxide ion* B.Carbonic ion C.Nitrogen ion D.Ammonia ion

4- How do you name secondary amides? A.Add an amic ending B.Add a secondary ending C. Add a upper case N in the front* D.You do nothing 5- Why did Wallace Hume Carothers call his invention Nylon 66? A.He made 66 of them B.He was 66 at the time C.reflects the six carbon atoms in adipic acid and hexamethylene diamine molecules.* D.There were 66 molecules of

Sources http://dl.clackamas.cc.or.us/ch106-05/nomencla 1.htm http:// www.mhhe.com/physsci/chemistry/carey/stude nt/olc/graphics/carey04oc/ref/ch20reactionsami des.html http://www.chemgapedia.de/vsengine/vlu/vsc/ en/ch/2/vlu/oxidation_reduktion/ red_amid_amin.vlu/Page/vsc/en/ch/2/oc/ reaktionen/formale_systematik/ oxidation_reduktion/reduktion/ ersatz_o_n_durch_h/ carbonsaeuren_und_derivate/amid_amin/ mechanismus_amid_amin.vscml.html http://techtransfer.universityofcalifornia.edu/ NCD/10299.html

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