Butadiene, C4H6, is a planar molecule that has the following carbon–carbon bond lengths:
(c) The middle C¬C bond length in butadiene (1.48 Å) is a little shorter than the average C¬C single bond length (1.54 Å). Does this imply that the middle C¬C bond in butadiene is weaker or stronger than the average C¬C single bond?

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Understand that bond length is inversely related to bond strength: shorter bonds are generally stronger.

Recognize that the middle C-C bond in butadiene is shorter (1.48 Å) than the average C-C single bond (1.54 Å).

Consider the concept of resonance in butadiene, which can lead to partial double bond character in the middle C-C bond.

Acknowledge that partial double bond character typically results in a bond that is shorter and stronger than a single bond.

Conclude that the middle C-C bond in butadiene is likely stronger than the average C-C single bond due to its shorter length and resonance effects.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Bond Length and Bond Strength

In general, shorter bond lengths indicate stronger bonds due to the increased overlap of atomic orbitals. Conversely, longer bonds tend to be weaker. This relationship is crucial for understanding how bond length can provide insights into the strength of a bond.

Resonance in Molecules

Butadiene exhibits resonance, where the actual structure is a hybrid of multiple contributing structures. This delocalization of electrons can lead to bond lengths that differ from typical single or double bonds, affecting their strength and stability.

Comparison of Bond Types

C–C single bonds and double bonds have distinct characteristics. A single bond is generally longer and weaker than a double bond. Understanding these differences helps in analyzing the bond lengths in butadiene and determining the relative strength of the middle C–C bond.

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Bonding Types

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Textbook Question

In ozone, O3, the two oxygen atoms on the ends of the molecule are equivalent to one another. (d) How many electrons are delocalized in the p system of ozone?

Textbook Question

Butadiene, C4H6, is a planar molecule that has the following carbon–carbon bond lengths:

(a) Predict the bond angles around each of the carbon atoms and sketch the molecule.

Textbook Question

Butadiene, C4H6, is a planar molecule that has the following carbon–carbon bond lengths:

(b) From left to right, what is the hybridization of each carbon atom in butadiene?

Textbook Question

The structure of borazine, B₃N₃H₆, is a six-membered ring of alternating B and N atoms. There is one H atom bonded to each B and to each N atom. The molecule is planar. (a) Write a Lewis structure for borazine in which the formal charge on every atom is zero.

Textbook Question

The structure of borazine, B₃N₃H₆, is a six-membered ring of alternating B and N atoms. There is one H atom bonded to each B and to each N atom. The molecule is planar. (c) What are the formal charges on the atoms in the Lewis structure from part (b)? Given the electronegativities of B and N, do the formal charges seem favorable or unfavorable? What are the formal charges on the atoms in the Lewis structure from part (b)?

Textbook Question

The structure of borazine, B₃N₃H₆, is a six-membered ring of alternating B and N atoms. There is one H atom bonded to each B and to each N atom. The molecule is planar. (e) What are the hybridizations at the B and N atoms in the Lewis structures from parts (a) and (b)? Would you expect the molecule to be planar for both Lewis structures? Would you expect the molecule to be planar for both Lewis structures?