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Write these reactions as proton-transfer reactions. Label which reactant is the acid and which is the base, which product is the conjugate base of the original acid, and which is the conjugate acid of the original base. In addition, write Lewis structures for each reactant and product, and use curved arrows to show the flow of electrons in each reaction. (a) \(\mathrm{CH}_{3} \mathrm{SH}+\mathrm{OH}^{-} \rightleftharpoons \mathrm{CH}_{3} \mathrm{~S}^{-}+\mathrm{H}_{2} \mathrm{O}\) (b) \(\mathrm{CH}_{2}=\mathrm{O}+\mathrm{HCl} \rightleftharpoons \mathrm{CH}_{2}=\mathrm{OH}^{+}+\mathrm{Cl}^{-}\)

Short Answer

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Question: Identify the acids, bases, conjugate acids, and conjugate bases in each reaction. Draw the Lewis structures of all reactants and products and show the flow of electrons using curved arrows. (a) Reaction: CH鈧僑H + OH鈦 鈫 CH鈧僑鈦 + H鈧侽 - Acid: CH鈧僑H - Base: OH鈦 - Conjugate Acid: H鈧侽 - Conjugate Base: CH鈧僑鈦 (b) Reaction: CH鈧=O + HCl 鈫 CH鈧=OH鈦 + Cl鈦 - Acid: HCl - Base: CH鈧=O - Conjugate Acid: CH鈧=OH鈦 - Conjugate Base: Cl鈦

Step by step solution

01

(a) Identify the acids and bases in the reaction

In the given reaction, \(\mathrm{CH}_{3}\mathrm{SH}\) reacts with \(\mathrm{OH}^{-}\) to form \(\mathrm{CH}_{3}\mathrm{S}^{-}\) and \(\mathrm{H}_{2}\mathrm{O}.\) In this case, \(\mathrm{CH}_{3}\mathrm{SH}\) donates a proton, so it is the acid. \(\mathrm{OH}^{-}\) accepts the proton, so it is the base.
02

(a) Identify conjugate acid and conjugate base

The conjugate base of the original acid, \(\mathrm{CH}_{3}\mathrm{SH},\) is \(\mathrm{CH}_{3}\mathrm{S}^{-},\) and the conjugate acid of the original base, \(\mathrm{OH}^{-},\) is \(\mathrm{H}_{2}\mathrm{O}.\)
03

(a) Drawing Lewis structures for reactants and products, and showing electron flow

In this reaction, the electron flow can be shown with the following curved-arrow notation: \(\mathrm{CH}_{3}\mathrm{SH}\: (\:\bullet \:)\:\bullet\: - \:\bullet \mathrm{O}^{-}H \rightleftharpoons \mathrm{CH}_{3}\mathrm{S}^{-}\: (\:\bullet \:)\:\bullet \: + \:\bullet \mathrm{O} H_{2}\) The arrow starts at the lone pair on the oxygen atom and points to the hydrogen atom in \(\mathrm{CH}_{3}\mathrm{SH}\) to show the proton transfer.
04

(b) Identify the acids and bases in the reaction

In the given reaction, \(\mathrm{CH}_{2}=\mathrm{O}\) reacts with \(\mathrm{HCl}\) to form \(\mathrm{CH}_{2}=\mathrm{OH}^{+}\) and \(\mathrm{Cl}^{-}.\) In this case, \(\mathrm{HCl}\) donates a proton, so it is the acid. \(\mathrm{CH}_{2}=\mathrm{O}\) accepts the proton, so it is the base.
05

(b) Identify conjugate acid and conjugate base

The conjugate base of the original acid, \(\mathrm{HCl},\) is \(\mathrm{Cl}^{-},\) and the conjugate acid of the original base, \(\mathrm{CH}_{2}=\mathrm{O},\) is \(\mathrm{CH}_{2}=\mathrm{OH}^{+}.\)
06

(b) Drawing Lewis structures for reactants and products, and showing electron flow

In this reaction, the electron flow can be shown with the following curved-arrow notation: \(\mathrm{C}=\mathrm{O}\:(\:\bullet \:)\:\bullet\: +\: \mathrm{H} \cdot \mathrm{Cl} \rightleftharpoons \mathrm{C}=\mathrm{OH}^{+}\: (\:\bullet \:)\:\bullet + \: - \mathrm{Cl}\) The arrow starts at the lone pair on the oxygen atom and points to the hydrogen atom in \(\mathrm{HCl}\) to show the proton transfer.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Acid-Base Chemistry
In acid-base chemistry, reactions between acids and bases play a crucial role. The exercise primarily revolves around proton-transfer reactions, where an acid donates a proton to a base. For example, in the reaction
  • o\(\mathrm{CH}_{3}\mathrm{SH}\)
  • \(\mathrm{OH}^{-}\) acts as a base and accepts the proton from \(\mathrm{CH}_{3}\mathrm{SH}\), which is acting as an acid.
This results in the generation of a conjugate base and acid. This interaction is aptly described by the Bronsted-Lowry acid-base theory. Understanding which molecule in a reaction acts as an acid and which as a base is foundational to predicting the course and outcome of these reactions.By identifying these substances correctly, students can gain insight into the mechanism of proton-transfer reactions, which is essential not only for academic learning but also for practical applications in chemistry.
Lewis Structures
Lewis structures are diagrams that show the bonding between atoms in a molecule, as well as the lone pairs of electrons that may exist. In proton-transfer reactions, drawing Lewis structures is helpful to visualize the electron configurations before and after the reaction. For example, consider the reaction of \(\mathrm{CH}_{3}\mathrm{SH}\) with \(\mathrm{OH}^{-}\). The Lewis structure of \(\mathrm{CH}_{3}\mathrm{SH}\) shows a sulfur-hydrogen bond where the sulfur atom can donate a proton (hydrogen) to \(\mathrm{OH}^{-}\).
  • When drawing Lewis structures for the reaction, indicate the lone pairs on atoms like oxygen and sulfur, which are critical as they engage in electron-pair interactions.
  • These diagrams help bridge the abstract concept of electron movement with visual representation, making the understanding of chemical reactions more tangible.
Electron Flow
Understanding electron flow is fundamental in grasping proton-transfer reactions in acid-base chemistry. The use of curved arrows in Lewis structures guides students to visualize and understand how electrons move during the reaction process. Take as an example the reaction of \(\mathrm{CH}_{2}=\mathrm{O}\) with \(\mathrm{HCl}\). Here:
  • The lone pairs on the oxygen atom in \(\mathrm{CH}_{2}=\mathrm{O}\) use the curved arrow notation to show how they form a bond with a proton (\(\mathrm{H}^{+}\)) from \(\mathrm{HCl}\).
  • These arrows establish a visual pathway representing the direction of electron flow, clarifying which bonds are broken and which new bonds are formed.
This visual tool significantly aids in the comprehension of chemical reactions, allowing for a detailed and step-by-step understanding of electron transactions during these interactions.
Conjugate Acid-Base Pairs
A conjugate acid-base pair consists of two species that transform into each other through the gain or loss of a proton. Recognizing these pairs is a key aspect of understanding acid-base reactions. Consider the reaction \(\mathrm{CH}_{3}\mathrm{SH}\) with \(\mathrm{OH}^{-}\):
  • \(\mathrm{CH}_{3}\mathrm{SH}\) donates a proton, which converts it into \(\mathrm{CH}_{3}\mathrm{S}^{-}\), its conjugate base.
  • When \(\mathrm{OH}^{-}\) accepts a proton, it becomes \(\mathrm{H}_{2}\mathrm{O}\), representing its conjugate acid.
These pairs show how substances are interrelated in their acidic and basic forms, further demonstrating the reversible nature of proton-transfer reactions.Understanding these relationships can aid students in predicting the outcomes of reactions and assist in developing a deeper grasp of equilibrium in chemical processes.

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Most popular questions from this chapter

Sodium hydride, NaH, is available commercially as a gray-white powder. It melts at \(800^{\circ} \mathrm{C}\) with decomposition. It reacts explosively with water and ignites spontaneously on standing in moist air. (a) Write a Lewis structure for the hydride ion and for sodium hydride. Is your Lewis structure consistent with the fact that this compound is a high- melting solid? Explain. (b) When sodium hydride is added very slowly to water, it dissolves with the evolution of a gas. The resulting solution is basic to litmus. What is the gas evolved? Why has the solution become basic? (c) Write an equation for the reaction between sodium hydride and 1-butyne, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH}\). Use curved arrows to show the flow of electrons in this reaction.

For each equation, label the Lewis acid and the Lewis base. In addition, show all unshared pairs of electrons on the reacting atoms, and use curved arrows to show the flow of electrons in each reaction. (a) \(\mathrm{F}^{-}+\mathrm{BF}_{3} \longrightarrow \mathrm{BF}_{4}^{-}\) (b)

Benzoic acid, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\left(\mathrm{p} K_{\mathrm{a}} 4.19\right)\), is only slightly soluble in water, but its sodium salt, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COO}^{-} \mathrm{Na}^{+}\), is quite soluble in water. In which solution(s) will benzoic acid dissolve? (a) Aqueous \(\mathrm{NaOH}\) (b) Aqueous \(\mathrm{NaHCO}_{3}\) (c) Aqueous \(\mathrm{Na}_{2} \mathrm{CO}_{3}\)

Answer True or False to the following statements about energy diagrams and reactions. (a) A reaction coordinate diagram is used to visualize the change in the internal energy of chemical structures that occurs during chemical reactions. (b) Thermodynamics is the study of the energies of structures that are represented by wells on reaction coordinate diagrams. (c) Kinetics is the study of the rates of chemical reactions. (d) One part of a reaction mechanism would be the understanding of which bonds break and form during a reaction. (e) Thermal reactions occur via collisions between molecules, and the more energy in those collisions the greater the rate of the reactions. (f) The enthalpy of a reaction is the sole determinant of whether it will or will not occur. (g) An exergonic reaction will always occur during the life span of the standard human being.

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