How is nitration of benzene accomplished?
By adding HNO3/H2SO4
How many methods are there to prepare amines and what are they?
6 methods
1. Reduction of nitrogen compounds
2. Ammonolysis of alkyl halides
3. Reduction of Nitriles
4. Reduction of amides
5. Gabriel Phthalimide synthesis
6. Hoffman bromamide degradation reaction
What are the methods in reduction of nitrogen compounds compounds?
what is the process of converting an alkyl halide into a alkyl nitrile?
Add ethanolic NaCN
When amine salts react with bases like NaOH what is formed?
The parent amine is regenerated along with water and the halogen
What is the anime salt?
+. -
R-NH2-X
Why do amines behave as nucleophiles?
Due to the presence of unshared electron pair.
Explain the solubility of amine salts.
Soluble in water but not in organic solvents like ether
Larger the Kb value
Stronger is the base
Base is strong if
pKb value is low or Kb value is high
What happen when RNH2 reacts with H20?
We get RNH3 (+) + OH (-)
Basicity of an amine is related to?
Their structure
What does basic character of an amine depend on.
Ease of formation of the cation by accepting a proton from the acid. More stable more basic
What does the basic character of an amine depend on?
On the ease of formation and stability of the cation (RNH₃⁺) after accepting a proton.
Why are alkylamines stronger bases than ammonia in the gaseous phase?
Due to the +I effect of alkyl groups and hyperconjugation, which increase electron density on nitrogen and stabilize the ammonium ion by dispersing the positive charge.
Order of basicity of amines in gaseous phase?
3° > 2° > 1° > NH₃
Why is the trend of amine basicity irregular in aqueous solution?
Because solvation and steric hindrance affect stability of ammonium ions.
How does solvation influence amine basicity in water?
Smaller cations form more H-bonds with water, are better solvated, and hence more stable. Larger/sterically hindered ions are less solvated → less stable.
Order of solvation (stability) of ammonium ions in water?
1° > 2° > 3°
Final order of basicity of amines in aqueous solution?
2° > 1° > 3° > NH₃ (due to balance of +I effect, solvation, and steric hindrance).
How many resonating structures for anilinium
2 (only the double bonds change.
What do you ad din Gabriel phthalimide synthesis and what happens?
KOH which replaces hydrogen and forms phthalimide sakt and heated with R-X where R replaces the halogen to form N-Alkylphthalimide. Then NaOH aq is added where ONa attached to both carbon and we get RNH2
Diaz onion salt formula
RN2X
How is Benzenediazonium prepared
Aniline + NaNo2 + HCl (HNO2 in situ) at 273-278K gives C6H5N2Cl + NaCl + H20