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Chapter 5: Problem 59

Arrange the following in the order of increasing acidity. Cc1cccc(C(=O)O)c1 Cc1ccc(C(=O)O)cc1 O=C(O)c1cccc(O)c1 O=C(O)c1ccccc1 \(\mathrm{A}\) \(C\) \(\mathrm{D}\) (a) \((\mathrm{A})<(\mathrm{D})<(\mathrm{B})<(\mathrm{C})\) (b) \((\mathrm{A})<(\mathrm{C})<(\mathrm{B})<(\mathrm{D})\) (c) \((\mathrm{C})<(\mathrm{D})<(\mathrm{A})<(\mathrm{B})\) (d) \((\mathrm{B})<(\mathrm{A})<(\mathrm{D})<(\mathrm{C})\)

Short Answer

Expert verified
Question: Arrange the following molecules in the order of increasing acidity based on their SMILES notation: 1. Cc1cccc(C(=O)O)c1 2. Cc1ccc(C(=O)O)cc1 3. O=C(O)c1cccc(O)c1 4. O=C(O)c1ccccc1 Answer: The correct order of increasing acidity is Toluic Acid (A) < p-Toluic acid (C) < Benzoic acid (D) < Salicylic acid (B).

Step by step solution

01

Identify the molecules

The first step is to identify the molecules given by their SMILES notation: 1. Cc1cccc(C(=O)O)c1 -> Toluic Acid 2. Cc1ccc(C(=O)O)cc1 -> p-Toluic acid 3. O=C(O)c1cccc(O)c1 -> Salicylic acid 4. O=C(O)c1ccccc1 -> Benzoic acid Now that we have identified the molecules, we can move forward and analyze their acidity.
02

Analyze acidity

We will analyze the acidity of the molecules based on the presence of electron-withdrawing groups, electron-donating groups, and the stability of their conjugate bases: 1. Toluic Acid: Methyl group (-CH3) at ortho position (electron-donating group) 2. p-Toluic acid: Methyl group (-CH3) at para position (electron-donating group) 3. Salicylic acid: Hydroxyl group (-OH) at ortho position (electron-donating group) and Carbonyl group (C=O) (electron-withdrawing group) 4. Benzoic acid: Carbonyl group (C=O) (electron-withdrawing group) Now, let's arrange them in the order of increasing acidity.
03

Arrange in increasing acidity order

Electron-donating groups decrease acidity, while electron-withdrawing groups increase acidity. In addition, the conjugate base's stability directly affects the acidity of the molecule. Therefore, the order of increasing acidity would be as follows: \(A\) (Toluic Acid) < \(C\) (p-Toluic acid) < \(D\) (Benzoic acid) < \(B\) (Salicylic acid) So the correct order is given by option (b) \((\mathrm{A})<(\mathrm{C})<(\mathrm{B})<(\mathrm{D})\).

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