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NEET · Chemistry · STD 12 - 6. Haloalkanes and Haloarenes

In the following reaction sequence, X and Z respectively are :
\( CH _3 CH _2 CH _2- OH + PCl _5 \longrightarrow CH _3 CH _2 CH _2 Cl +X+ HCl \)
\( CH _3 CH _2 CH _2 Cl \xrightarrow[\Delta]{\text { alc. } KOH } Y \xrightarrow[\left( C _6 H _5 CO \right)_2 O _2]{ HBr } Z\)

  1. A \(X= POCl _3 ; Z= CH _3- CH ( Br )- CH _3\)
  2. B \(X=POCl_3 ; Z=CH_3 CH_2 CH_2-Br\)
  3. C \(X= H _3 PO _3 ; Z= CH _3- CH ( Br )- CH _3\)
  4. D \(X= H _3 PO _3 ; Z= CH _3 CH _2 CH _2- Br\)
Verified Solution

Answer & Solution

Correct Answer

(B) \(X=POCl_3 ; Z=CH_3 CH_2 CH_2-Br\)

Step-by-step Solution

Detailed explanation

(B) \(X=POCl_3 ; Z=CH_3 CH_2 CH_2-Br\)
Reaction of primary alcohol with \(PCl _5\) gives alkyl chloride, \(POCl _3\), and HCl
\(CH_3 CH_2 CH_2 OH+PCl_5 \longrightarrow CH_3 CH_2 CH_2 Cl+POCl_3+HCl\)
Thus, \(X= POCl _3\).
Dehydrohalogenation of 1-chloropropane with alcoholic KOH yields propene.
\(CH_3 CH_2 CH_2 Cl \xrightarrow{\text { alc. } KOH, \Delta} CH_3 CH=CH_2\)
Thus, \(Y= CH _3 CH = CH _2\).
Addition of HBr to propene in the presence of peroxide follows anti-Markovnikov addition.
\(CH_3 CH=CH_2+HBr \xrightarrow{\left(C_6 H_5 CO\right)_2 O_2} CH_3 CH_2 CH_2 Br\)
Thus, \(Z= CH _3 CH _2 CH _2 Br\).