What is the solvent medium in which bromination of acetanilide is carried out?
Furthermore, bromination is carried out in aqueous medium evading the use of chlorinated solvents. In a conical flask acetanilide (1 g, 0.008 mol) was dissolved in ethanol (15 ml).
Why is acetanilide preferred over aniline for a bromination?
Bromination of aniline would result in a trisubstitution. A monosubstitution is desired, so aniline is acetylated to give acetanilide because the amino group of aniline is too reactive.
Which is more reactive aniline or anisole?
Aniline > anisole because N is less electronegative than O, less induction deactivatingAniline > acetanilide because the C=O. group makes the nitrogen less resonance electron donating.
Is aniline soluble in water?
However, in aniline, due to the large hydrophobic part, i.e., hydrocarbon part, the extent of H-bonding decreases considerably, and hence aniline is insoluble in water.
Is acetanilide soluble in water?
WaterBenzeneEthanolAcetoneDiethyl ether
Acetanilide/Soluble in
Why is aniline more reactive than Acetanilide?
Resonance delocalization to the carbonyl oxygen is favored because of the electronegativity of oxygen. Since the nitrogen lone pair electrons are less available to the ring than in aniline, the ยท reactivity of the ring toward electrophilic substitution decreases.
Which is more basic anisole or aniline?
Aniline is a much stronger base than anisole, and so the strongly-acidic conditions used for most electrophilic aromatic substitution reactions convert the NH2NH2 group on aniline into NH+3NH3+, which is strongly deactivating. In order to do conventional aromatic substitution on aniline, you must first acylate it.
What is the role of acetic acid during bromination of aniline?
Aniline when treated with bromine in acetic acid or water gives a product of 2,4,6- tribromo aniline. It is white precipitate. But we want certain position bromination means we first do acylated aniline to get acetanilide. Acetanilide is treated with bromine in acetic acid mainly gives p-Bromoacetanilide.
Why ethanoic acid is used in bromination of anisole?
Anisole undergoes bromination with bromine in ethanoic acid, due to activation of benzene ring by the methoxy group para isomer is obtained.
Is Acetanilide soluble in water?
Why does aniline not dissolve in water?
Since there is no electronegative atom in toluene, the bonding formed between toluene and water is a van der Waal interaction which is a weaker interaction than the hydrogen bonding. So this weak van der Waal interaction cannot compensate for the strong already existing hydrogen bonding in the water.
How is the solubility of acetanilide?
Slightly soluble in water; very soluble in ethanol and acetone; soluble in ethyl ether.
Why is acetanilide soluble in warm water?
water and very soluble in boiling water? acetanilide will dissolve into the heated water due to its high solubility in boiling water but will drop out of solution and crystallize in room temperature water due to its low solubility in cold water.
Is acetanilide less basic than aniline?
Acetanilide is less basic than aniline.
Why does the reactivity of gets reduced in acetanilide?
Lone pair of electrons present on amino group are in conjugation with benzene ring in aniline. But due to presence of acyl group in conjugation with amino group in acetanilide, lone pair of electrons on NH2 are no longer in resonance with benzene ring. This is the reason, activity of NH2 is reduced in acetanilide.
Why is aniline very reactive towards bromination?
This is because NH2 group in aniline is highly activating group. A lone pair of electrons is present on N which releases the electron density to the benzene ring and hence activates the benzene ring towards electrophilic substitution reactions at ortho and para positions.