How to prepare p-bromoaniline, knowing that aniline only gives the tris-brominated product; note that bromination of aniline does not stop at the monobrominated stage and cannot be moderated by using only one equivalent of bromine.

SOLUTION:

Moderating the activity of NH₂ by reacting of aniline with acetic anhydride

The activating influence of NH₂ has been reduced due to competing withdrawal of N-lone pair by carbonyl group:

Related Questions:

1. Why do not Friedel-Crafts reactions succeed on aromatic rings that are substituted either by a strongly electron-withdrawing group such as carbonyl (C=O) or by an amino group (-NH₂, NHR, -NR₂):
2. Why does not aniline undergo Friedel crafts reactions explain?
3. Why Friedel–Crafts alkylations often give polysubstitution products but Friedel–Crafts acylations do not.

What Is Mustard Gas?

Mustard gas is a colorless oily liquid whose vapor is a powerful irritant and vesicant, used in chemical weapons. Mustard gas, or sulphur mustard (Cl-CH₂CH₂)₂S, is a chemical agent that causes severe burning of the skin, eyes and respiratory tract. It can be absorbed into the body through inhalation, ingestion or by coming into contact with the skin or eyes

Sulphur Mustard:

Nitrogen Mustard:

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5. Aspirin: Acetylsalicylic acid:
6. Capsaicin: use in pepper sprays used for personal defense and topical creams used for pain relief:
7. What is the structure and use of Westron and Westrosol?

Why does aqueous sodium bicarbonate solution dissolve carboxylic acids but not phenol though they are also acidic ?

In both cases the product formed is carbonic acid (pKa=6) which is stronger acid than phenols (pKa=10) but weaker than carboxylic acid(pKa=4.5).

Acid-base equilibrium in second case shift more towards backward direction. Hence phenol does not react with NaHCO3.

Why enol form of Beta Dicarbonyl compound more stable than those of monocarbonyl compounds?

Enol form of Beta Dicarbonyl compounds are more stable because it has a conjugated π-system and intramolecular H-bonding.

Why enol form of phenol is more stable than its keto isomers?

Enol form of Phenol is more stable than keto form because it has a stable aromatic ring.