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Chapter 4: Problem 69

Equal quantities of \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{Cl}\) and \(\mathrm{CH}_{3} \mathrm{Cl}\) are treated with iodide ion in acetone. Which reacts faster? (a) both react at almost equal rate (b) \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{Cl}\) reacts faster (c) \(\mathrm{CH}_{3} \mathrm{Cl}\) reacts faster (d) \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{Cl}\) doest not reacts at all

Short Answer

Expert verified
Answer: (b) CH3OCH2Cl reacts faster.

Step by step solution

01

Identify the reaction type

The reaction taking place in this problem is nucleophilic substitution, where the iodide ion (I-) acts as the nucleophile, attacking the carbon atom that is bonded to the chlorine atom in both the given compounds.
02

Determine the mechanism

For a nucleophilic substitution reaction, there are two common mechanisms: SN1 and SN2. In this case, both compounds are primary alkyl halides (primary carbon bound to a halogen). Primary alkyl halides typically undergo the SN2 mechanism due to steric reasons, as SN1 mechanism is favored by more substituents around the reactive site.
03

Compare the leaving groups

In both cases, the leaving group is a chlorine atom. The leaving group ability for both compounds is the same, as they both have chlorine attached to them.
04

Compare the nucleofuges

The nucleofuge is the part of the molecule that is not involved in the nucleophilic substitution but helps stabilize the transition state or facilitate the reaction. In the case of \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{Cl}\), the nucleofuge is the OCH2 group, whereas, in the case of \(\mathrm{CH}_{3} \mathrm{Cl}\), the nucleofuge is simply a hydrogen atom. For SN2 reactions, the stability of the transition state is important, and the presence of an electron-withdrawing group such as OCH2 makes the transition state more stable and facilitates the reaction.
05

Determine the faster-reacting compound

Based on the analysis, it is clear that the compound with the OCH2 group as the nucleofuge, \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{Cl}\), will have a more stable transition state and will likely react faster via the SN2 mechanism. Therefore, the correct answer is: (b) \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{Cl}\) reacts faster.

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