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Exercises · 4.20

Q.The skeletal structure of CH3COOHCH_3COOH as shown below is correct, but some of the bonds are shown incorrectly. Write the correct Lewis structure for acetic acid.

The book's printed skeletal structure of acetic acid with some bonds drawn incorrectly
Figure
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The textbook gives a skeletal structure of CH3COOHCH_3COOH with two bonds drawn incorrectly: a double bond between hydrogen and the methyl carbon (impossible — hydrogen can only ever form one bond), and a single bond between the carbonyl carbon and one oxygen (leaves both that carbon and that oxygen with an incomplete octet). Fixing both — H–C single, C=O double — gives the correct Lewis structure.

The structure exactly as given (incorrect)

    H   :O:
    |    |
H = C — C — O — H
    |
    H

This is the actual structure printed in the exercise. Two of its bonds are wrong, and the question asks you to identify and correct them — not to build a fresh structure from scratch.

Step 1: Find the chemically impossible bond

Look at the far left: the structure shows H=CH = C, a double bond between a hydrogen atom and the methyl carbon. This cannot be right. Hydrogen has exactly one valence electron, occupying a single 1s orbital — it can share that one electron in exactly one bond. A hydrogen atom can never be double-bonded to anything. This bond must be a plain single bond, H–CH–C.

Step 2: Check what that leaves incomplete

With the H–C bond corrected to single, count the bonds on each carbon:

  • Left (methyl) carbon: three C–H single bonds + one C–C single bond = 4 bonds — octet satisfied. ✓
  • Right (carbonyl) carbon: one C–C single bond + one C–O single bond (to the top oxygen) + one C–O single bond (to the –OH group) = only 3 bonds — octet incomplete.
  • Top oxygen: shown with a single bond to carbon plus only 2 lone pairs (4 electrons) = 6 electrons total — octet incomplete (a singly-bonded terminal oxygen needs 3 lone pairs to reach 8; a doubly-bonded one needs 2).

Both the carbonyl carbon and the top oxygen are short an octet — that is the second error hiding in the given structure.

Step 3: Fix the second bond

The carbonyl carbon needs one more bond, and the top oxygen needs 2 more electrons to complete its octet. Both are fixed by the same single change: make the C–O bond to the top oxygen a double bond (C=O) instead of single.

  • Carbonyl carbon now has: one C–C single bond + one C=O double bond + one C–O single bond (to –OH) = 4 bonds — octet satisfied. ✓
  • Top oxygen now has: one C=O double bond (4 electrons) + 2 lone pairs (4 electrons) = 8 electrons — octet satisfied. ✓

Step 4: Verify the electron count …

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