Question

The addition of \(\mathrm{KI}\) increases the rate of the reaction \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} 1+\mathrm{H}_{2} \mathrm{O} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}+\mathrm{HCl}\) This is because I is a (1) good nucleophile and a good leaving group (2) a poor nucleophile and a poor leaving group (3) a poor nucleophile and a good leaving group (4) a good nucleophile and a poor leaving group

Short answer

Option (1) is correct because \( \text{I}^- \) is a good nucleophile and a good leaving group.

Step-by-step solution

Understand the role of \(\text{KI}\)

\( \text{KI} \left( \text{Potassium Iodide} \right) \) dissociates in aqueous solution to form \(\text{K}^+ \) and \(\text{I}^- \). The \(\text{I}^- \) ion is the active species in the reaction.

Identify the nature of the iodide ion (\(\text{I}^-\))

\(\text{I}^-\) is known to be a good nucleophile because it is larger and more polarizable, allowing it to donate electrons effectively. Additionally, \(\text{I}^-\) is considered a good leaving group because it can stabilize the negative charge after departure.

Relate to the reaction mechanism

The reaction \(\mathrm{CH_3CH_2Cl + H_2O \rightleftharpoons\mathrm{CH_3CH_2OH + HCl}}\) is influenced by the presence of a good nucleophile and leaving group. The \(\text{I}^-\) functions well in this role, speeding up the reaction.

Evaluate the options

Given our conclusion that \(\text{I}^-\) is both a good nucleophile and a good leaving group, option (1) correctly describes the reason for the increased reaction rate.

Key concepts

nucleophile

A nucleophile is a chemical species that donates an electron pair to form a chemical bond. In the context of the reaction discussed, the iodide ion \(\text{I}^-\) acts as a nucleophile. Nucleophiles are generally negatively charged or neutral molecules with lone pairs of electrons.
Large, polarizable ions like \(\text{I}^-\) are particularly effective nucleophiles. They can donate their electrons more easily, which speeds up reactions. For the reaction \(\text{CH}_3\text{CH}_2\text{Cl + H}_2\text{O} \rightarrow \text{CH}_3\text{CH}_2\text{OH + HCl}\), the iodide ion aids by attacking carbon atoms, making it possible for the reaction to proceed more quickly.

leaving group

A leaving group is a part of a molecule that detaches during a chemical reaction, taking a pair of electrons with it. The effectiveness of a leaving group is crucial in determining the rate of many reactions. In this scenario, \(\text{I}^-\), which forms from the dissociation of potassium iodide \(\text{KI}\), acts as a very good leaving group.
The iodide ion is able to stabilize the negative charge after it detaches, which makes it a good leaving group. Effective leaving groups, like \(\text{I}^-\), help facilitate the breakdown of bonds, thus speeding up the reaction rate.

reaction mechanism

The reaction mechanism refers to the step-by-step sequence of elementary reactions by which overall chemical change occurs. In the reaction \(\text{CH}_3\text{CH}_2\text{Cl + H}_2\text{O} \rightarrow \text{CH}_3\text{CH}_2\text{OH + HCl}\), the mechanism involves a substitution process.
\(\text{KI}\) dissociates into \(\text{K}^+\) and \(\text{I}^-\) in water. The nucleophile \(\text{I}^-\) attacks the carbon bonded to chlorine in \(\text{CH}_3\text{CH}_2\text{Cl}\). This attack helps break the \(\text{C-Cl}\) bond, with \(\text{Cl}^-\) leaving.
Once the \(\text{Cl}^-\) leaves, \(\text{I}^-\) is poised to be replaced by \(\text{OH}^-\) from \(\text{H}_2\text{O}\), resulting in the formation of ethanol \(\text{CH}_3\text{CH}_2\text{OH}\). This detailed step-by-step breakdown showcases how the iodide ion serves its dual role as both a good nucleophile and leaving group.

Potassium iodide

Potassium iodide \(\text{KI}\) is an ionic compound that readily dissolves in water, forming potassium cations \(\text{K}^+\) and iodide anions \(\text{I}^-\).
The iodide ion is significant in organic chemistry reactions due to its efficiency both as a nucleophile and a leaving group. This dual role makes it particularly useful in enhancing reaction rates and facilitating smoother reaction mechanisms.
In the described reaction, potassium iodide's dissociation provides the necessary \(\text{I}^-\) ions that engage as active participants, helping to increase the overall rate of conversion from \(\text{CH}_3\text{CH}_2\text{Cl}\) to \(\text{CH}_3\text{CH}_2\text{OH}\).