Chapter 17 and GHW#7 Questions Amines and Amides

Bonding Characteristics of Amines & Amides Hydrocarbons compounds containing nitrogen are the focus of the chapter 17 on amines and amides. Amines are carbon-hydrogen-nitrogen compounds, derived form ammonia Amides contain oxygen in addition to these elements. Amines and amides occur widely in living organisms..

Hydrogen bonding in Amines N-H N hydrogen bonds are weaker than O-H O

Physical Properties of Amines

Hydrogen bonding in Amides

Odor or smell of Amines Most other amines are liquids and have odors resembling that of raw fish (strong, disagreeable odors). Foul smell from dead fish and decaying flesh is due to diamines released by the bacterial decomposition of protein. Examples: putrescine and cadaverine.

Common Names of Amines

IUPAC Nomenclature of Amines

Common/IUPAC Nomenclature of Amides

1. Identify the amines and amides from the following and give their common and/or IUPAC names. a)Type:_____________ Name:______________ b) Type:___________________ Name:__________________ c)Type:___________________ Name:__________________ d)Type:____________ Name:______________ e) Type:___________________ Name:__________________ f) Type:___________________ Name:__________________

1. Identify the amines and amides from the following and give their common and/or IUPAC names. g) Type:___________________ Name:__________________ h) Type:___________________ Name:__________________ i) Type:___________________ Name:__________________ j) Type:___________________ Name:__________________ k) Type:___________________ Name:__________________ l) Type:___________________ Name:__________________

Cyclic Amines

1. Identify the amines and amides from the following and give their common and/or IUPAC names. m) Type:___________________ Name:__________________ n) Type:___________________ Name:__________________ o) Type:___________________ Name:__________________

Basicity: Amine Salt formation Amines have a basic PH PH> 7

2. Classify each of the following as either 1', 2', or 3' amines and quaternary amine :

3. Consider the following compounds: a) CH 3 —CH 2 —CH 2 —NH 2 b) CH 3 —CH 2 —NH—CH 3 c) CH 3 —CH 2 —CH 2 —CH 3 d) CH 3 —CH 2 —CH 2 —NH 3 + Cl - A.Arrange compounds in the order highest boiling point to lowest? B. Arrange compounds in the order of highest solubility in water to the lowest?

4. Draw the structure of the following amines and amides: a) N-methyl-1- butanamine: b) N-methylaniline c) N-phenyl-3- chlorobutanamide d) N-ethyl-N- methylethanami de e) N-methylbenzamide

Preparation of Amines a)Reaction of ammonia with alkyl halides b) Reduction of amides c) Reduction of Nitro Groups

Preparation of Amines a)Reaction of ammonia with alkyl halides b) Reduction of amides c) Reduction of Nitro Groups

Preparation of Amides a)Reaction with carboxylic acid to form amides (described below in preparation of amides) b)Polymerization to form polyamides Nylon 66 – a polymer of hexanedioic acid and 1,6- hexanediamine as monomers shown below

Chemical Reactions of Amides a)Hydrolysis reaction amides (Acid/base hydrolysis) b)Reduction of amides to amines

5) Name and complete the following preparations/reactions of amines and amides: a) b) c) d)

5) Name and complete the following preparations/reactions of amines amides: e) f) g)

5) Name and complete the following preparations/reactions of amines amides: h) i) j) k)

5) Name and complete the following preparations/reactions of amines amides: l) m) n)

Drugs & Narcotics

Heterocyclic Amines and Alkaloids Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.[5]

Heterocyclic Amines and Alkaloids

Cocaines

Chlorophyll and Hemoglobin

Purines and Pyrimidines: DNA Bases