For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(b)

Verified step by step guidance

1. Identify the functional groups in the molecule. The structure contains two carboxylic acid groups (-COOH) and a chlorine atom attached to the cyclohexane ring.
2. Determine the reactivity of the molecule with a strong base. Carboxylic acids are acidic and will react with a strong base to form their conjugate base, the carboxylate anion (-COO⁻). The chlorine atom may also influence the reactivity due to its electron-withdrawing nature.
3. Predict the reaction of the strong base with the carboxylic acid groups. A single equivalent of a strong base will deprotonate one of the carboxylic acid groups, forming a carboxylate anion and leaving the other carboxylic acid group intact.
4. Consider the position of the chlorine atom. The chlorine atom is electron-withdrawing and may stabilize the carboxylate anion formed near it, making the carboxylic acid group closer to the chlorine more likely to be deprotonated.
5. Write the expected product. The molecule will have one carboxylic acid group converted to a carboxylate anion (-COO⁻), while the other carboxylic acid group remains unchanged. The chlorine atom remains attached to the cyclohexane ring.

Key Concepts

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. In organic chemistry, strong bases can deprotonate acidic functional groups, such as alcohols or carboxylic acids, leading to the formation of alkoxide ions or carboxylate ions. Understanding the acidity of functional groups is crucial for predicting the products of these reactions.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the provided molecule, the chlorine atom is a good leaving group, and when a strong base is present, it can facilitate the substitution reaction, leading to the formation of new products.

Functional Group Reactivity

Different functional groups exhibit varying reactivities based on their electronic properties. In the given molecule, the presence of hydroxyl (-OH) and carbonyl (C=O) groups influences how the molecule interacts with a strong base. Recognizing the reactivity of these groups is essential for predicting the outcome of the reaction and the stability of the resulting products.