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COMEDK · Chemistry · 25. Haloalkanes and Haloarenes

Both reactions (i) and (ii) give the same compound X as the major product. Identify X
(i). 3-Methylbut-1-ene \(+\mathrm{HCl} \rightarrow \mathrm{X}\)
(ii). Neopentyl alcohol \(+\mathrm{HCl}\left(\right.\) anh. \(\left.\mathrm{ZnCl}_2\right) \rightarrow \mathrm{X}\)

  1. A \(\left(\mathrm{CH}_3\right)_2-\mathrm{CCl}_{-}-\mathrm{CH}_2-\mathrm{CH}_3\)
  2. B \(\left(\mathrm{CH}_3\right)_2-\mathrm{CH}-\mathrm{CH}_2-\mathrm{CH}_2 \mathrm{Cl}\)
  3. C \(\left(\mathrm{CH}_3\right)_2-\mathrm{CH}-\mathrm{CHCl}-\mathrm{CH}_3\)
  4. D \(\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}\left(\mathrm{CH}_3\right)-\mathrm{CH}_2 \mathrm{Cl}\)
Verified Solution

Answer & Solution

Correct Answer

(A) \(\left(\mathrm{CH}_3\right)_2-\mathrm{CCl}_{-}-\mathrm{CH}_2-\mathrm{CH}_3\)

Step-by-step Solution

Detailed explanation

In reaction (i), the electrophilic addition of \(\mathrm{HCl}\) to 3-methylbut-1-ene proceeds via the formation of a carbocation. The initial protonation of the double bond yields the secondary carbocation \((CH_3)_2CH-CH^{+}-CH_3\). This secondary carbocation undergoes a…