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Ch. 2 - Acids and Bases; Functional Groups
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 2 - Acids and Bases; Functional GroupsProblem 12a,b
Chapter 2, Problem 12a,b

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

Verified step by step guidance
1
Identify the acids and bases in each reaction. In reaction (a), CH3Li acts as a base and H—C≡C—H acts as an acid. In reaction (b), CH3Li is the base and (CH3)3C—OH is the acid.
Determine the pKa values of the acids involved using the provided appendix. For H—C≡C—H, the pKa is approximately 25, and for (CH3)3C—OH, the pKa is around 18.
Consider the solvents provided: pentane, diethyl ether, ethanol, water, and ammonia. Evaluate their compatibility based on polarity and ability to dissolve ionic compounds.
For reaction (a), choose a solvent that can stabilize the ionic species formed, such as diethyl ether, which is a common solvent for organolithium compounds due to its ability to solvate ions.
For reaction (b), consider the polarity of the solvent needed to dissolve the alcohol and the resulting alkoxide. Ethanol or water could be suitable due to their polar nature and ability to dissolve ionic species.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Solvent Polarity

Solvent polarity is crucial in determining the compatibility of solvents with acids and bases in a reaction. Polar solvents, like water and ethanol, can stabilize ionic species through solvation, while non-polar solvents, like pentane, are better suited for reactions involving non-polar compounds. Understanding the polarity helps predict solvent interactions with reactants and products.
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Acid-Base Chemistry

Acid-base chemistry involves the transfer of protons between molecules, which is central to the reactions given. The strength of acids and bases, often measured by pKa values, determines the direction and extent of these reactions. Knowing the relative acidity or basicity of the reactants helps in selecting a solvent that won't interfere with the acid-base equilibrium.
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The Lewis definition of acids and bases.

Solvent Compatibility

Solvent compatibility refers to the ability of a solvent to dissolve reactants and products without participating in side reactions. For example, ammonia can act as a base, potentially affecting acid-base reactions, while diethyl ether is a common inert solvent that can dissolve a wide range of organic compounds. Choosing a compatible solvent ensures the reaction proceeds as intended without unwanted interactions.
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Related Practice
Textbook Question

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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Textbook Question

Write equations for the following acid–base reactions. Label the conjugate acids and bases, and show any inductive stabilization. Predict whether the equilibrium favors the reactants or products. Try to do this without using a table of pKa values, but if you need a hint, you can consult Appendix 4.

g. NaOCH2CH3 + Cl2CHCH2OH

h. H2Se + NaNH2

i. CH3CHFCOOH + FCH2CH2COO–

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Textbook Question

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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Textbook Question

Write equations for the following acid–base reactions. Label the conjugate acids and bases, and show any inductive stabilization. Predict whether the equilibrium favors the reactants or products. Try to do this without using a table of pKa values, but if you need a hint, you can consult Appendix 4.

a. CH3CH2OH + CH3NH−

b. F3CCOONa + Br3C—COOH

c. CH3OH + H2SO4

Textbook Question

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. 

c.

d.

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Textbook Question

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

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