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Ch. 2 - Acids and Bases; Functional Groups
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Wade 9th EditionCh. 2 - Acids and Bases; Functional Groups문제 10a,b,c
2장, 문제 10a,b,c

Write equations for the following acid–base reactions. Use the information in Table 2-2 or Appendix 4 to predict whether the equilibrium will favor the reactants or the products.
a. HCOOH + –CN
b. CH3COO– + CH3OH
c. (CH3)2CHOH + NaNH2

검증된 단계별 안내
1
Identify the acid and base in each reaction. For reaction (a), HCOOH is the acid and -CN is the base. For reaction (b), CH3COO- is the base and CH3OH is the acid. For reaction (c), (CH3)2CHOH is the base and CH3OH is the acid.
Write the chemical equation for each reaction. For (a), the equation is: HCOOH + -CN → HCOO- + HCN. For (b), the equation is: CH3COO- + CH3OH → CH3COOH + CH3O-. For (c), the equation is: (CH3)2CHOH + CH3OH → (CH3)2CHO- + CH3OH2+.
Determine the pKa values of the acids and conjugate acids involved in each reaction using the provided tables. For (a), pKa of HCOOH is 3.76 and pKa of HCN is 9.22. For (b), pKa of CH3OH is 15.5 and pKa of CH3COOH is 4.74. For (c), pKa of CH3OH is 15.5 and pKa of (CH3)2CHOH is 15.9.
Predict the direction of equilibrium based on the pKa values. The equilibrium will favor the side with the weaker acid (higher pKa value). For (a), equilibrium favors the products because HCN is a weaker acid than HCOOH. For (b), equilibrium favors the reactants because CH3OH is a weaker acid than CH3COOH. For (c), equilibrium slightly favors the reactants because (CH3)2CHOH is a weaker acid than CH3OH.
Summarize the findings: In reaction (a), the equilibrium favors the formation of HCOO- and HCN. In reaction (b), the equilibrium favors the formation of CH3COO- and CH3OH. In reaction (c), the equilibrium slightly favors the formation of (CH3)2CHOH and CH3OH.

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주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. An acid donates a proton, while a base accepts it. Understanding the nature of the reactants and products as acids or bases is crucial for predicting the direction of the reaction and writing balanced chemical equations.
추천 영상:
02:49
The Lewis definition of acids and bases.

Equilibrium and Reaction Favorability

In chemical reactions, equilibrium refers to the state where the rates of the forward and reverse reactions are equal. The position of equilibrium indicates whether reactants or products are favored. This can be predicted using the relative strengths of acids and bases, often found in tables of pKa values, where a lower pKa indicates a stronger acid.
추천 영상:
04:00
Determining Acid/Base Equilibrium

pKa and Acid-Base Strength

The pKa value is a quantitative measure of the strength of an acid in solution. It is the negative logarithm of the acid dissociation constant (Ka). A lower pKa value indicates a stronger acid, which more readily donates protons. Comparing pKa values of the acids and conjugate acids in a reaction helps predict the direction of equilibrium.
추천 영상:
07:45
Identifying pKa values
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교과서 질문

Calculate the pH of the following solutions.

a. 5.00 g of HBr in 100 mL of aqueous solution

b. 1.50 g of NaOH in 50 mL of aqueous solution

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교과서 질문

Ammonia appears in [TABLE 2-2 ] as both an acid and a conjugate base. a. Explain how ammonia can act as both an acid and a base. Which of these roles does it commonly fill in aqueous solutions?

b. Show how water can serve as both an acid and a base.

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교과서 질문

Ammonia appears in [TABLE 2-2] as both an acid and a conjugate base.

d. Show how methanol (CH3OH) can serve as both an acid and a base. Write an equation for the reaction of methanol with sulfuric acid.

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교과서 질문

Ethanol, methylamine, and acetic acid are all amphoteric, reacting as either acids or bases depending on the conditions.

a. Rank ethanol, methylamine, and acetic acid in decreasing order of acidity. In each case, show the equation for the reaction with a generic base (B:−) to give the conjugate base.

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교과서 질문

Ethanol, methylamine, and acetic acid are all amphoteric, reacting as either acids or bases depending on the conditions.

b. Rank ethanol, methylamine, and acetic acid in decreasing order of basicity. In each case, show the equation for the reaction with a generic acid (HA) to give the conjugate acid.

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교과서 질문

For each of the following reactions, suggest which solvent(s) would be compatible with the acids and bases involved. (We will ignore any other possible reactions for now.) Your choices of solvents are pentane, diethyl ether, ethanol, water, and ammonia. Refer to Appendix 4 for any needed values of pKa, or estimate them.

a. CH3Li + H—C≡C—H → CH4 + H—C≡CLi

b. CH3Li + (CH3)3C—OH → CH4 + (CH3)3C—OLi

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