Sample of $2, 3 - d i b r o m o - 3 - m e t h y l p e n t a n e$ is heated with zinc dust, the resulting product is isolated and heated with $H I$ in the presence of phosphorus. Indicate which structure represents the final product of the reactions

C H_{2} = C H - C H_{3} | C H - C H_{2} - C H_{3}

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C H_{3} - C H_{2} - C | C H_{3} H - C H_{2} - C H_{3}

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C H_{3} - C H I - C | C H_{3} H - C H_{2} - C H_{3}

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None of the above

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Solution

The correct option is B $C H_{3} - C H_{2} - C | C H_{3} H - C H_{2} - C H_{3}$
$C H_{3}$ $C H_{3}$
$C H_{3} - C H | - | C | - C H_{2} - C H_{3} + Z n ⟶ C H_{3} - C H = | C - C H_{2} - C H_{3} + Z n B r_{2}$
$B r$ $B r$ $↓ H I / Red P$
$C H_{3} - C H_{2} - C H | - C H_{2} - C H_{3}$
$C H_{3}$
$3-Methyl pentane$

$Z n$ brings dehalogenation of $2, 3 - d i b r o m o - 3 - m e t h y l p e n t a n e$ to give $3 - m e t h y l p e n t - 2 - e n e$ which undergoes reduction to get the corresponding alkane on treating with $H I / P$ .

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A g N O_{3}

C H_{3} - C H_{3}, C H_{2} = C H_{2}

C H \equiv C H

S_{N} 2

K I

C H_{3} - C H_{2} - C H_{2} - C H_{2} - C l a n d C H_{3} - C H ∣ C H_{3} - C H_{2} - C l

(I) (I I)

C H_{3} - C H_{2} - C H_{2} - C l a n d C H_{3} - C H_{2} - C H_{2} - B r

(I) (I I)

C H_{3} - C H ∣ C H_{3} - C H_{2} - C H_{2} - C l a n d C H_{3} - C H_{3} ∣ C ∣ C H_{3} - C H_{2} C l

(I) (I I)

C H_{3} - C H_{2} - C H_{2} - B r ∣ C H - C H_{3} a n d C H_{3} - C H_{3} ∣ C H - C H_{2} - B r ∣ C H - C H_{3}

(I) (I I)

A . C H_{3} - C H = C H_{2} + H C l ⟶ C H_{3} - C | C l H - C H_{3}

B . C H_{3} - C H = C H_{2} + H B r ⟶ C H_{3} - C H_{2} - C H_{2} B r

C . C H_{3} - C H = C H_{2} + H B r p e r o x i d e - ---- \to C H_{3} - C H_{2} - C H_{2} - B r

D . C H_{3} - C H = C H_{2} + H I p e r o x i d e - ---- \to C H_{3} - C | I H - C H_{3}

C H_{3} - C H_{2} - C H_{2} - C H_{2} - C H | C H_{3} - C | C H_{3} - C H_{3} - C H_{2} - C H_{3} | C H - C H_{2} - C H_{2} - C H_{2} - C H_{3}

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