Problem: In terms of the bonds present, explain why acetic acid, CH 3CO2H, contains two distinct types of carbon-oxygen bonds, whereas the acetate ion, formed by loss of a hydrogen ion from acetic acid, only contains one type of carbon-oxygen bond. The skeleton structures of these species are shown:

FREE Expert Solution

We are being asked to differentiate the C-O bond of acetic acid (CH3CO2H) and acetate ion (CH3CO2-). We will have to draw the Lewis Structure of acetic acid (CH3CO2H) and acetate ion (CH3CO2-) first and determine if there are resonance structures possible. 


To solve this problem we shall follow these general steps for each molecule:

Step 1: Determine the central atom of the molecule.

Step 2: Calculate the total number of valence electrons present.

Step 3: Draw the Lewis Structure.

Step 4: Identify resonance form or structures, if any. 


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Problem Details

In terms of the bonds present, explain why acetic acid, CH 3CO2H, contains two distinct types of carbon-oxygen bonds, whereas the acetate ion, formed by loss of a hydrogen ion from acetic acid, only contains one type of carbon-oxygen bond. The skeleton structures of these species are shown:

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What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Resonance Structures concept. You can view video lessons to learn Resonance Structures. Or if you need more Resonance Structures practice, you can also practice Resonance Structures practice problems.