The rate low for the hydrolysis of thioacetamide, CH3 CSNH2, CC(=S)NCOCC(N)=O I

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The rate low for the hydrolysis of thioacetamide, CH3 CSNH2,...

The rate low for the hydrolysis of thioacetamide, $\mathrm{CH}_{3} \mathrm{CSNH}_{2}$, <smiles>CC(=S)NCOCC(N)=O</smiles> Is rate $=\mathrm{k}\left[\mathrm{H}^{+}\right]$[TA], where TA is thioacetamide. In which of the following solutions, will the rate of hydrolysis of thioacetamide (TA) is least at $25^{\circ} \mathrm{C}$ ? (a) $0.1 \mathrm{M}$ in $\mathrm{TA}$ and $0.20 \mathrm{M}$ in $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$ (b) $0.1 \mathrm{M}$ in $\mathrm{TA}$ and $0.20 \mathrm{M}$ in $\mathrm{HNO}_{3}$ (c) $0.1 \mathrm{M}$ in TA and $0.20 \mathrm{M}$ in $\mathrm{HCO}_{2} \mathrm{H}$ (d) $0.15 \mathrm{M}$ in TA and $0.15 \mathrm{M}$ in $\mathrm{HCl}$

The rate low for the hydrolysis of thioacetamide, $\mathrm{CH}_{3} \mathrm{CSNH}_{2}$,
<smiles>CC(=S)NCOCC(N)=O</smiles>
Is rate $=\mathrm{k}\left[\mathrm{H}^{+}\right]$[TA], where TA is thioacetamide. In which of the following solutions, will the rate of hydrolysis of thioacetamide (TA) is least at $25^{\circ} \mathrm{C}$ ?
(a) $0.1 \mathrm{M}$ in $\mathrm{TA}$ and $0.20 \mathrm{M}$ in $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$
(b) $0.1 \mathrm{M}$ in $\mathrm{TA}$ and $0.20 \mathrm{M}$ in $\mathrm{HNO}_{3}$
(c) $0.1 \mathrm{M}$ in TA and $0.20 \mathrm{M}$ in $\mathrm{HCO}_{2} \mathrm{H}$
(d) $0.15 \mathrm{M}$ in TA and $0.15 \mathrm{M}$ in $\mathrm{HCl}$

Key Concepts

Rate Law and Reaction Kinetics

The rate law expresses the reaction rate in terms of the concentrations of the reactants. In this context, the hydrolysis of thioacetamide follows a rate equation that is first order in both the hydrogen ion concentration and the concentration of thioacetamide. This demonstrates the fundamental kinetic principle that the amount of reactant and the conditions (such as proton concentration) can directly influence the speed of the chemical reaction.

Acid Catalysis

Acid catalysis involves the acceleration of a chemical reaction by the presence of an acid, typically through the donation of protons (H+). In the reaction under discussion, the rate is directly proportional to the [H+] concentration, indicating that acids play a crucial role in facilitating the hydrolysis process. This concept underscores the idea that even in reactions where the reactant is not an acid, the presence of protons can help stabilize intermediates or transition states, thereby increasing the reaction rate.

Acid Strength and Acid Dissociation Constant (Ka)

The acid dissociation constant, Ka, measures the strength of an acid in solution. Strong acids (with higher Ka values) dissociate almost completely to produce H+ ions, while weak acids (with lower Ka values) produce far fewer H+ ions at the same concentration. In the context of the problem, the disparity in acid strengths among different acids leads to different effective proton concentrations, which in turn affects the rate of hydrolysis.

Effect of pH on Reaction Rate

The pH of a solution is a measure of its hydrogen ion concentration and is thus intimately related to the reaction rate in acid-catalyzed processes. Since the rate of hydrolysis is proportional to [H+], variations in pH—dictated by the acid's strength and concentration—can significantly alter the reaction rate. A lower pH (higher [H+]) results in a faster reaction, whereas a higher pH (lower [H+]) slows the reaction down.

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