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Ch.9 - Molecular Geometry and Bonding Theories
Chapter 9, Problem 102b

Butadiene, C4H6, is a planar molecule that has the following carbon–carbon bond lengths:
Chemical structure of butadiene with bond lengths: HC≡C at 1.20 Å and C−CH3 at 1.48 Å.
(b) From left to right, what is the hybridization of each carbon atom in butadiene?

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Key Concepts

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

Hybridization

Hybridization is a concept in chemistry that describes the mixing of atomic orbitals to form new hybrid orbitals. These hybrid orbitals are used to form covalent bonds in molecules. In butadiene, the hybridization of carbon atoms can be determined by the types of bonds they form, such as single, double, or triple bonds.
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Hybridization

Bond Lengths

Bond lengths are the average distances between the nuclei of two bonded atoms. They provide insight into the type of bond present; for example, triple bonds are generally shorter than double bonds, which are shorter than single bonds. In butadiene, the bond lengths of 1.20 Å and 1.48 Å indicate the presence of a triple bond and a single bond, respectively.
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Planarity of Molecules

The planarity of a molecule refers to its geometric arrangement in a two-dimensional plane. In butadiene, the planar structure allows for effective overlap of p-orbitals, which is essential for the formation of π bonds in double bonds. This planarity is crucial for understanding the hybridization and bonding characteristics of the carbon atoms in the molecule.
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Square planar complexes show the most complex splitting pattern.
Related Practice
Textbook Question

Sodium azide is a shock-sensitive compound that releases N2 upon physical impact. The compound is used in automobile airbags. The azide ion is N3-. (b) State the hybridization of the central N atom in the azide ion.

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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?

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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.

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Textbook Question

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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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.

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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?

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