Arrange the following CH3CH2CH2Cl(I), CH3CH2–CHCl–CH3 (II), (CH3)2CHCH2Cl (III) and (CH3)3C –Cl (IV) in order of decreasing tendency towards SN 2 reaction

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Arrange the following
CH₃CH₂CH₂Cl(I), CH₃CH₂–CHCl–CH₃ (II),
(CH₃)₂CHCH₂Cl (III) and (CH₃)₃C –Cl (IV) in order of decreasing tendency towards S_N 2 reaction

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I > III > II > IV

III > IV > II > I

II > I > III > IV

IV > III > II > I

answer is A.

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Detailed Solution

In SN² reactions, the attack of nucleophile occurs from the back side on the carbon atom carrying the halogen. Therefore, presence of bulky substituents on or near this carbon atom tends to hinder the approach of the nucleophile to the a-carbon due to steric hindrance and thus makes the reaction difficult to occur. Thus, the reactivity in SN² reactions follows the following order
CH₃CH₂CH₂Cl(I)>(CH₃)₂CHCH2Cl(III)>CH₃−CH₂−CHCl−CH₃(II)>(CH₃)₃C−Cl(IV).