Amides Flashcards
Amide Bond
C to N single bond
Amide Outline
Carboxylic acid derivative with NRR’ group replacing OH
Primary Amine Outline
N attached to 2 Hs. Strongest bonds (all H bonds) and increase boiling point
Secondary amine outline
N attached to 1 H and another substituent
Tertiary amine outline
N attached to no Hs. Have 2 other substituents. weakest of all bonds (no H bonds) and low boiling point
How do primary amines bind to eachother
Dorm 3 H bonds. Dimers
How do tertiary amines bind to eachotehr
0 H bonds
How do secondary amines bind to eachother
2 H bonds
4 Unique properties of amines
C to N triagonal planar gemoetry, C to N bond is shorter then average single (due to single to double bond resonance), C isn’t as electrophilic (not as reactive) and N is only slightly nucleophilic despite lone pair of electrons
Why do amines have unique properties
Resonance structures. Alternate between C to N single and double bonds (lose electron lone pair, N = positive). Alternate between C to O double and single bonds (O becomes negative). When double bond between C and N the distance is much shorter the ususal thus atoms are better able to share electrons (less nucleophilic/electrophilic)
Amino Acids Outline
Contains amine and carboxylic acid. Linked by amide bonds (aka peptide bonds). Unique properties enable stronger and longer lasting bonds (due to C and N not being as reactive)
Peptide bonds geometry
6 atoms are planar geometry due to zig zagging. Trans configuration to peptide bonds. Unreactive to aqueous environment in body and limited configuration around bonds
Amides Synthesis
Reaction of amines with carboxylic acid derivatives (ammonia = primary amide, NH2R = secondary amide, NRR’ = tertiary amide). Either HCl, carboxylic acid or alcohol is byproduct
