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Haloalkanes and Haloarenes question

2024 · 27 Jan · Shift 2 · Q7
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Haloalkanes and Haloarenes question

2024 · 27 Jan · Shift 2 · Q7

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Identify B formed in the reaction. Cl−(CH2)4−Cl→ excess NH3 A→NaOHB+H2O+NaCl\mathrm{Cl}-\left(\mathrm{CH}_2\right)_4-\mathrm{Cl} \xrightarrow{\text { excess } \mathrm{NH}_3} \mathrm{~A} \xrightarrow{\mathrm{NaOH}} \mathrm{B}+\mathrm{H}_2 \mathrm{O}+\mathrm{NaCl}Cl−(CH2​)4​−Cl excess NH3​​ ANaOH​B+H2​O+NaCl
  1. A
    JEE Main 2024 (Online) 27th January Evening Shift Chemistry - Haloalkanes and Haloarenes Question 41 English Option 1
  2. B
    JEE Main 2024 (Online) 27th January Evening Shift Chemistry - Haloalkanes and Haloarenes Question 41 English Option 2
  3. C
    Cl−N+H3−(CH2)4−N+H3Cl−\stackrel{-}{\mathrm{Cl}}\stackrel{+}{\mathrm{N}} \mathrm{H}_3-\left(\mathrm{CH}_2\right)_4-\stackrel{+}{\mathrm{N}} \mathrm{H}_3 \mathrm{Cl}^{-}Cl−N+​H3​−(CH2​)4​−N+​H3​Cl−
  4. D
    H2N−(CH2)4−NH2\mathrm{H}_2 \mathrm{N}-\left(\mathrm{CH}_2\right)_4-\mathrm{NH}_2H2​N−(CH2​)4​−NH2​
View written solutionFree

Correct answer: D

  1. Identify the starting compound

The given compound is: Cl−(CH2)4−Cl\mathrm{Cl}-(\mathrm{CH}_2)_4-\mathrm{Cl}Cl−(CH2​)4​−Cl which is 1,4-dichlorobutane.

  1. Reaction with excess ammonia

Alkyl halides react with excess NH3\mathrm{NH_3}NH3​ via nucleophilic substitution. Since there are two chlorine atoms, both can be replaced by amino groups.

First, substitution gives ammonium salts, and finally the corresponding diamine is formed.

So intermediate AAA is the diammonium salt: Cl− H3N+−(CH2)4−NH3+ Cl−\mathrm{Cl^-}\,\mathrm{H_3N^+}-(\mathrm{CH}_2)_4-\mathrm{NH_3^+}\,\mathrm{Cl^-}Cl−H3​N+−(CH2​)4​−NH3+​Cl− This corresponds to the salt of butane-1,4-diamine.

  1. Action of NaOH on A

NaOH\mathrm{NaOH}NaOH deprotonates the ammonium groups:

\rightarrow \mathrm{H_2N}-(\mathrm{CH}_2)_4-\mathrm{NH_2} + 2\mathrm{NaCl} + 2\mathrm{H_2O}$$ Thus, $B$ is: $$\mathrm{H_2N}-(\mathrm{CH}_2)_4-\mathrm{NH_2}$$ 4. **Match with options** The product $B$ is **butane-1,4-diamine**, which is given in **Option D**. 5. **Comparison with stored answer** Stored correct answer: **D** Derived answer: **D** They match.
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