Explain why:
(i) Ethylamine is soluble in water but aniline is not.
(ii) Aniline does not undergo Friedel Crafts reaction.
(iii) Aniline is acetylated before bromination.
Explain why:
(i) Ethylamine is soluble in water but aniline is not.
(ii) Aniline does not undergo Friedel Crafts reaction.
(iii) Aniline is acetylated before bromination.
1. Ethylamine is soluble in water owing to its potential to form intermolecular Hydrogen bonds with water. On the other hand aniline does not undergo hydrogen bonding because of the presence of the benzene which is highly hydrophobic. Therefore aniline is insoluble in water.
2. Aniline is a very strong base and when it reacts with acidic AlCl3 it forms a salt. Due to the formation of the salt a net positive charge develops of Nitrogen which deactivates further electrophillic substitution in the benzene ring.
3. Amine group creates a strong electron density at the ortho and para positions which leads to the formation of tribromoaniline. In order to isolate mono bromoaniline acetylation is done first that results in the formation of bromoacetanilide. Since it is electron donating it prevents bromine from attaching there and we get the desired product.
1. Ethylamine is soluble in water owing to its potential to form intermolecular Hydrogen bonds with water. On the other hand aniline does not undergo hydrogen bonding because of the presence of the benzene which is highly hydrophobic. Therefore aniline is insoluble in water.
2. Aniline is a very strong base and when it reacts with acidic AlCl3 it forms a salt. Due to the formation of the salt a net positive charge develops of Nitrogen which deactivates further electrophillic substitution in the benzene ring.
3. Amine group creates a strong electron density at the ortho and para positions which leads to the formation of tribromoaniline. In order to isolate mono bromoaniline acetylation is done first that results in the formation of bromoacetanilide. Since it is electron donating it prevents bromine from attaching there and we get the desired product.
