Consider the following sequence of reactions. (see structure) Total number of $\mathrm{sp}^{3}$ hybridised carbon atoms in the major product C formed is ______.

JEE Main · 2025 · 23 Jan 2025 · Shift 2 · Compounds Containing Nitrogen

Consider the following sequence of reactions.

(see structure)

Total number of

sp^{3}

hybridised carbon atoms in the major product C formed is ______.

Answer: 4

Solution

The nitro-substituted aniline is diazotised with

NaNO X_{2} / HCl

at 0–5 °C to give a diazonium salt, which couples with the phenol under basic conditions to form an azo dye linking the two aromatic rings through a

- N = N -

bridge; the phenolic

- OH

of this azo compound is then converted to an ethyl ether by Williamson synthesis (NaOH, then ethyl bromide) to give the major product C, matching the molecular formula

C X_{16} H X_{18} N X_{2} O X_{2}

. The only

s p^{3}

carbons introduced anywhere in this sequence are those of the two ethoxy (

- O - CH X_{2} - CH X_{3}

) groups, since every aromatic-ring carbon and the azo nitrogens are not sp3 carbons. Each ethoxy group contributes two

s p^{3}

carbons (the

CH X_{2}

and the

CH X_{3}

), and there are two such groups in C, giving a total of 4

s p^{3}

-hybridised carbon atoms.

JEE Main · 2025 · 23 Jan 2025 · Shift 2 · Integer answer

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JEE Main · 2025 · 23 Jan 2025 · Shift 2 · Compounds Containing Nitrogen

Solution

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