Q.Write chemical name of NH2-NHCONH2.
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🔒 Start your 14-day free trial to unlock the full solution →Concept understanding — Carbonyl Compound Derivatives of Ammonia (Hydrazine, Semicarbazide, Phenylhydrazine, Hydroxylamine)
Why Carbonyl Compounds React With "Ammonia Derivatives"
You already know that aldehydes and ketones are attacked by nucleophiles at their electrophilic carbonyl carbon. A whole family of nitrogen nucleophiles — all built by replacing one or more hydrogens of ammonia (NH₃) — reacts this way, and each gives a crystalline, easily purified, sharp-melting-point derivative. This made them classic tools (before modern spectroscopy) for identifying an unknown aldehyde or ketone. But exams don't just ask "which reagent forms which derivative" — they also test whether you know each reagent's exact structural formula, because it's easy to misremember one.
The Four Standard Derivatives, and Their Correct Formulas
- Hydrazine: HX2N−NHX2 — two NH₂ groups joined directly. Reacts with a carbonyl to form a hydrazone.
- Phenylhydrazine: CX6HX5−NH−NHX2 — hydrazine with only ONE of its two nitrogens bearing a phenyl group; the other end stays as a free –NH₂. Reacts with a carbonyl to form a phenylhydrazone.
- Semicarbazide: HX2N−NH−CO−NHX2 — the hydrazine nitrogen chain extended into a urea-like carbonyl unit. Reacts with a carbonyl to form a semicarbazone.
- Hydroxylamine: HX2N−OH (also written NHX2OH) — ammonia with one H replaced by –OH. Reacts with a carbonyl to form an oxime.
A very common exam trap: writing phenylhydrazine as CX6HX5−NH−NH−CX6HX5 — i.e., putting a phenyl group on BOTH nitrogens. That structure would actually be 1,2-diphenylhydrazine (hydrazobenzene), a completely different compound. Real phenylhydrazine has exactly one phenyl group and one free –NH₂ left to attack the carbonyl carbon.
The Reaction Pattern (Nucleophilic Addition–Elimination)
All four reagents follow the same two-step logic at the carbonyl carbon:
RX2C=O+HX2N−NuRX2C(OH)(NHNu)RX2C=N−Nu+HX2O
The nitrogen's lone pair (nucleophile) first adds across the C=O π bond (nucleophilic addition), and the resulting unstable intermediate then eliminates a water molecule to form a stable C=N bond — so the overall process is an addition–elimination (condensation) reaction, not a simple addition.
Why This Matters …
The structure combines a hydrazine unit (H2N-NH-) with a urea-like carbonyl group (-CO-NH2), a combination given its own specific name because of how it reacts with carbonyl compounds. …
NH2-NHCONH2 is semicarbazide, a hydrazine derivative widely used to form solid, characterisable semicarbazone derivatives of aldehydes and ketones.
The structure NH2-NH-CO-NH2 consists of a hydrazine unit (H2N-NH-) attached to a urea-like carbonyl (-CO-NH2); this compound is called semicarbazide. …
- CBSE 2024Set ANNUAL1 markQ.Write chemical name of NH2-NHCONH2.
›Reveal solutionSolution
NH2-NHCONH2 is semicarbazide, a hydrazine derivative widely used to form solid, characterisable semicarbazone derivatives of aldehydes and ketones.
The structure NH2-NH-CO-NH2 consists of a hydrazine unit (H2N-NH-) attached to a urea-like carbonyl (-CO-NH2); this compound is called semicarbazide. …
- CBSE 2022Set E1 markMCQQ.When formaldehyde reacts with NH3, then which of the following compounds is formed ?(a) Formaldehyde ammonia(b) Hexamethylene tetramine(c) Formalin(d) Methylamine
›Reveal solutionSolution
Formaldehyde reacts with ammonia to form hexamethylenetetramine (urotropine).
6 HCHO + 4 NH3 -> (CH2)6N4 + 6 H2O
The product, hexamethylenetetramine (also called urotropine), is a cage-like compound used as a urinary antiseptic and in the manufacture of the explosive RDX.
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- CBSE 2019Set ANNUAL1 markQ.Draw structure of cyclopropanone oxime.
›Reveal solutionSolution
An oxime forms when a ketone's C=O reacts with hydroxylamine (NH₂OH) to give C=N–OH. Cyclopropanone oxime is this applied to the three-membered ring ketone cyclopropanone.
Cyclopropanone is the smallest cyclic ketone: a three-membered carbocyclic ring, (CH2)2C=O, i.e. two –CH₂– groups and one carbonyl carbon closing the ring.
An oxime is formed by the condensation of a ketone (or aldehyde) with hydroxylamine, with loss of water:
R2C=O+H2N−OH→R2C=N−OH+H2O
Applying this to cyclopropanone: the ring carbonyl carbon's C=O is converted to C=N–OH, while the ring itself (the two –CH₂– groups completing the three-membered ring) is retained.
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- CBSE 2018Set ANNUAL1 markMCQQ.Chemical formula of urotropine is:(a) (CH2)4N3(b) (CH2)5N4(c) (CH2)6N4(d) (CH2)3N3
›Reveal solutionSolution
Urotropine (hexamethylenetetramine) is the cage-like condensation product of formaldehyde and ammonia, formula (CH2)6N4.
Urotropine, also called hexamethylenetetramine or methenamine, is formed by the condensation of six molecules of formaldehyde (an aldehyde) with four molecules of ammonia:
6HCHO+4NH3→(CH2)6N4+6H2O
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