Textbook Question
What is the conjugate base of each of the following acids? [The most acidic proton is indicated.]
(d)
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3. Acids and Bases
Acids and Bases
1:14 minutesProblem 66c
Textbook Question
For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(c) 
Verified step by step guidance1
Identify the functional groups in the molecule. The structure contains a hydroxyl group (-OH) on the left side and a carboxylic acid group (-COOH) on the right side.
Determine the reactivity of the functional groups with a strong base. A strong base will deprotonate the most acidic hydrogen in the molecule. The carboxylic acid group is more acidic than the hydroxyl group due to resonance stabilization of the carboxylate anion.
Predict the site of deprotonation. The hydrogen attached to the oxygen in the carboxylic acid group will be removed by the strong base, forming a carboxylate anion (R-COO⁻).
Write the resulting structure after deprotonation. Replace the hydrogen in the carboxylic acid group with a negative charge on the oxygen atom, indicating the formation of the carboxylate anion.
Consider the stability of the product. The carboxylate anion is stabilized by resonance, making it the favored product of the reaction with a strong base.
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1mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Strong Bases in Organic Chemistry
Strong bases, such as sodium hydroxide (NaOH) or potassium tert-butoxide (KOtBu), are capable of deprotonating weak acids. In organic chemistry, they are often used to initiate reactions by removing protons from functional groups, such as alcohols or carboxylic acids, leading to the formation of alkoxides or carboxylate ions.
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Deprotonation of Alcohols
Alcohols contain hydroxyl (-OH) groups that can act as weak acids. When a strong base is introduced, it can deprotonate the alcohol, resulting in the formation of an alkoxide ion. This process is crucial in many organic reactions, as the alkoxide can act as a nucleophile in subsequent steps.
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Reaction Mechanisms
Understanding reaction mechanisms is essential for predicting the products of chemical reactions. In this case, the mechanism involves the deprotonation of hydroxyl groups by a strong base, leading to the formation of reactive intermediates that can further react with other molecules, ultimately determining the final product of the reaction.
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