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Heterocyclic amines and Amides.
Heterocyclic amines, alkaloids and amides.
17
Organic Chemistry
Undergraduate 2
03/07/2015

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Cards

Term
What is a heterocyclic amine?
Definition
A cyclic organic compound that containes one or more nitrogen atoms in a ring.
Term
What are the most common heterocyclic amine rings?
Definition
5 or 6 atom rings with one or more nitrogen atoms.
Term
What is the name of a heterocyclic amine with 4 carbon, 2 nitrogen and no double bonds?
Definition
Pyrrolidine
Term
What is the name of a heterocycline amine with 4 carbon, one nitrogen and 2 double bonds?
Definition
Pyrrole
Term
What is the name of an heterocyclic amine with 3 carbon, 2 nitrogen atoms and two double bonds?
Definition
Imidazole
Term
What do you call a six atom heterocyclic amine with 1 nitrogen and no double bonds?
Definition
Piperidine
Term
What do you call a six atom heterocyclic amine with 1 nitrogen and three double bonds?
Definition
Pyridine
Term
What do you call a heterocyclic amine with 4 carbon atoms, 2 nitrogen and three bonds?
Definition
Pyrimidine
Term
What are alkaloids?
Definition
Physiologicaly active nitrogen containing compounds produced by plants.  "Alali-like"
Term
How are amides created?
Definition
Using a reaction called amidation.
Term
What is amidation?
Definition
When a carboxylic acid reacts with ammonia or a primary or secondary amine.  Water is removed and the carboxylic acid and amine molecules join to form an amide.  (Like Esters)
Term
What amides can undergo the amidation process?
Definition

Primary and secondary amines, because a hydrogen has to be lost.

 

CH3-CH2-C-OH + NH2-CH3 -> CH3-CH2-C-NH-CH3 + H2O

            ||                                        ||

             O                                         O

Propanoic acid + Methylamine-> N-Methylpropanamide + water

Term
What is the IUPAC naming convention for Amides?
Definition

Remove the -ic acid or -oic acid from the carboxylic acid names, then add the suffix amide.

 

CH3-C-NH2

||

O

Ethanamide

Term
What do you call a benzene ring with an amide group?
Definition
Benzamide
Term
What is the relative melting points for amides?
Definition
High for primary amides, lower for secondary and low for tertiary as there are no hydrogen bonds available to bind with other amdes.
Term
How water soluble are amides?
Definition
One to five are soluble in water due to hydrogen bondings.
Term
What is hydrolysis of amides?
Definition

The reverse reaction of amide formation (the removal of water).  With the addition of water and acid, the amide bond is split creating te carboxylic acid and ammonia/amine.

 

CH3-C-NH2 + HOH + HCL -> CH3-C-OH + NH4Cl

       ||                                         ||

       O                                          O

Ethanamide -> Ethanoic acid + ammonium chloride.

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