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Chapter 4: Problem 167

Which of the following compounds will undergo hydrolysis most readily by \(\mathrm{S}_{\mathrm{N}} 1\) mechanism?

Short Answer

Expert verified
Answer: ____________ To determine the compound that will most readily undergo hydrolysis by an SN1 mechanism, consider the following factors: 1. Substrate structure: Tertiary carbocations (3°) are more reactive than secondary (2°) and primary (1°) carbocations. 2. Leaving group: Good leaving groups, such as halogens or sulfonate ions, increase the likelihood of an SN1 reaction. 3. Solvent: Polar protic solvents, like water, alcohols, and carboxylic acids, are more suitable for SN1 reactions. Compare the given compounds based on these factors, and identify the one with the most desirable combination for favorable SN1 reactivity.

Step by step solution

01

Identifying the substrate structure

The substrate structure affects the reactivity towards SN1 reactions. Tertiary carbocations (3°) are the most stable and will readily undergo SN1 reactions, followed by secondary (2°) and primary (1°) carbocations. We should examine the given compounds for their structural classification as primary, secondary, or tertiary substrates.
02

Assessing the leaving group

The likelihood of a molecule undergoing an SN1 reaction can also be influenced by the leaving group. A good leaving group will make it more likely for a compound to undergo an SN1 reaction. Generally, good leaving groups are those that can stabilize the negative charge after leaving. Halogens like Cl-, Br-, and I- are typically good leaving groups, as are sulfonate ions like \(\mathrm{CH}_{3}\mathrm{SO}_{3}^{-}\). Compare the leaving groups of the given compounds to help determine which compound will most readily undergo hydrolysis by an SN1 mechanism.
03

Examining the solvent

The solvent used in the reaction can also influence the probability of an SN1 reaction occurring. Generally, polar protic solvents are more suitable for SN1 reactions because they can stabilize intermediate carbocations and transition states. Common polar protic solvents include water (H2O), alcohols (ROH), and carboxylic acids (R-COOH). If the given compounds include information about the solvent used, take this into consideration when determining which compound will most readily undergo hydrolysis by an SN1 mechanism.
04

Comparing the compounds

After identifying the substrate structure, leaving group, and solvent used for each of the given compounds, compare them to determine which compound best meets the criteria for favorable SN1 reactivity. The compound with the most desirable combination of these factors will likely be the one that undergoes hydrolysis by an SN1 mechanism the most readily.
05

Concluding the most readily hydrolysed compound

Based on the analysis of the substrate structure, leaving group, and solvent, identify which compound among the given list will most readily undergo hydrolysis by an SN1 mechanism.

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Most popular questions from this chapter

The product \(\mathrm{P}\) in the following reaction is \(\mathrm{ClCH}_{2}-\mathrm{CH}_{2} \mathrm{OH} \stackrel{\mathrm{OH}^{-}}{\longrightarrow} \mathrm{P}\)

\(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}+\mathrm{Cl}_{2} \stackrel{800 \mathrm{~K}}{\longrightarrow} \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}+\mathrm{HCl}\). This reaction takes place mainly by (a) \(\mathrm{S}_{\mathrm{N}} 1\) mechanism (b) \(\mathrm{S}_{\mathrm{N}} 2\) mechanism (c) free radical mechanism (d) E1 mechanism

The reaction which is wrongly represented among the following is (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2} \mathrm{Cl}+\mathrm{NaI} \underset{\Delta}{\stackrel{\text { acetone }}{\longrightarrow} \mathrm{CH}_{3}-\mathrm{CH}_{2} \mathrm{I}+\mathrm{NaCl}}\) (b) \(\mathrm{CH}_{3} \mathrm{COOAg}+\mathrm{Br}_{2} \stackrel{\mathrm{CCl}_{4} / \mathrm{reflux}}{\longrightarrow} \mathrm{CH}_{3} \mathrm{Br}+\mathrm{AgBr}+\mathrm{CO}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{COOAg}+\mathrm{I}_{2} \stackrel{\mathrm{CCl}_{4} / \text { reflux }}{\longrightarrow} \mathrm{CH}_{3} \mathrm{I}+\mathrm{AgI}+\mathrm{CO}_{2}\) (d) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}_{2}+\mathrm{Cl}_{2} \stackrel{775 \mathrm{~K}}{\longrightarrow} \mathrm{ClCH}_{2}-\mathrm{CH}=\mathrm{CH}_{2}+\mathrm{HCl}\)

Which of the following is the correct order of ease of displacement of groups in substitution reactions? (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{3}^{-}>\mathrm{CH}_{3} \mathrm{COO}^{-}>\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}\) (b) \(\mathrm{CH}_{3} \mathrm{COO}^{-}>\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}>\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{3}^{-}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{3}^{-}>\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}>\mathrm{CH}_{3} \mathrm{COO}^{-}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}>\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{SO}_{3}^{-}>\mathrm{CH}_{3} \mathrm{COO}^{-}\)

The reagent (s) that can be used to distinguish between methanol and ethanol are (a) Anhydrous \(\mathrm{ZnCl}_{2} / \mathrm{con} . \mathrm{HCl}\) (b) salicylic acid/con. \(\mathrm{H}_{2} \mathrm{SO}_{4}\) (c) Acetic anhydride (d) \(\mathrm{I}_{2} / \mathrm{NaOH}\)
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