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Why is Bezoic acid non polar, while its conjugate base is a polar molecule?

Why is Bezoic acid non polar, while its conjugate base is a polar molecule?

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Why is Bezoic acid non polar, while its conjugate base is a polar molecule?

 

**Benzoic Acid** The image features the chemical structure of benzoic acid. It consists of a benzene ring, which is a hexagonal arrangement of six carbon atoms, with alternating double bonds. Attached to this ring is a carboxyl group (-COOH). - **Benzene Ring:** The hexagonal structure with alternating single and double bonds. This cyclic structure contributes to the aromaticity of benzoic acid. - **Carboxyl Group (-COOH):** Attached to one of the carbon atoms in the benzene ring, this group consists of a carbon double-bonded to an oxygen atom (C=O) and singly bonded to a hydroxyl group (OH). Benzoic acid is a simple aromatic carboxylic acid commonly used in food preservatives and various chemical applications.
Transcribed Image Text:**Benzoic Acid** The image features the chemical structure of benzoic acid. It consists of a benzene ring, which is a hexagonal arrangement of six carbon atoms, with alternating double bonds. Attached to this ring is a carboxyl group (-COOH). - **Benzene Ring:** The hexagonal structure with alternating single and double bonds. This cyclic structure contributes to the aromaticity of benzoic acid. - **Carboxyl Group (-COOH):** Attached to one of the carbon atoms in the benzene ring, this group consists of a carbon double-bonded to an oxygen atom (C=O) and singly bonded to a hydroxyl group (OH). Benzoic acid is a simple aromatic carboxylic acid commonly used in food preservatives and various chemical applications.
Expert Solution
Step 1

Given benzoic acid ,C6H5COOH is a non polar Molecule, because it contains non polar , hydrophobic phenyl ring , as a major part. 

It also contains carboxylic acid part , which is slightly polar in nature , and hydrophilic in nature. 

When it is treated with sodium or sodium hydroxide NaOH then it gives sodium benzoate - 

C6H5COOH  + Na ------> C6H5COONa + 1/2H2

C6H5COOH + NaOH ------> C6H5COONa + H2O 

 

Sodium benzoate , is completely soluble in water , and contain sodium cation with benzoate anion - 

C6H5COONa -------> C6H5COO- + Na+

Thus, it is polar in nature. 

The benzoic acid and it's conjugate base can be related as - 

C6H5COOH <===> C6H5COO- + H+

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