Chapter 22-Amines
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What are Amines derived from?
Ammonia (NH3)
Draw out the following: -Primary Amines -Secondary Amines -Tertiary Amines
What is the name of naturally occuring amines?
Alkaloids
What is the geometry of an amine?
Triginal Planar
How many carbons can an amine be soluble in water?
Less than five carbons.
Which type of amines have high boiling points and why?
Primary and secondary amines will always have higher boiling points because they can intermoleculary H-bond.
Suffix for Amine (Nomenclature)
“-amine”
Prefix for Amine (Nomenclature)
“amino-“
What is aminobenzene also known as?
Aniline
Can amines have chirality?
No! Amines are not optically active.
pKb of Ammonia
4.74
pKa of Ammonium Ion
9.26
True or False: Aryl Amines are less basic than Alkyl Amines.
True, essentially the lone pair on the amine is now delocalized due to the aromatic ring and its pi energy, therefore it is less available to act as a base.
How can an Amine be protonated?
By either a weak or strong acid.
Does the presence of an Electron Withdrawing Group (EWG) or the presence of an Electron Donating Group (EDG) increase basicity?
The presence of an EDG will increase the basicity/
Are amines better nucleophiles or better electrophiles?
Amines are good nucleophiles. (Think: strong base=good nucleophile)
What happens when an amine goes under akylation?
The amine will NOT stop reacting, therefore causing it to become a quantenary ammonium salt, making it better nucleophile the more it becomes alylated.
What is a Hoffman Elimination? Show by doing the mechanism for the following reaction.
What is an imine? (Hint: Draw it out)
What reactants/reagents are used in Hoffman Elimination?
-Methyl Iodine (CH3I) -Ag2O, H2O, and Heat. -Amine
What is following reaction known as?
Reductive Animation
What forms in reductive animation?
An imine!
What can you reduce an imine with?
1) LAH, H2O 2) NaBH4, ROH 3) NaBH(OAc)3, ROH 4) NaCNBH3, ROH
Provide a mechanism using Acylation Reduction for the following reaction:
