) Which of the following is the least volatile?(1) CH3-CH2 -CH2-F(2) CH3-CH2-CH2_-Cl(3) CH,-CH-CH,(4) CH3 -CH2-CH2 Br

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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)

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

C H_{3} - C H_{2} - C H_{2} - C H_{2} - B r + C H_{3} O^{-} C H_{3} O H - ---- \to 60^{o} C P r o d u c t (I)

C H_{3} - C H_{2} - C H_{2} - C H_{2} - B r + (C H_{3})_{3} C O^{-} (C H_{3})_{3} C - O H - -------- \to 60^{o} C P r o d u c t (I I)

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