Ch. 2 - General Chemistry Translated: Finding the Electrons

Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition

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Mullins 1st Edition

Ch. 2 - General Chemistry Translated: Finding the Electrons

Problem 41

Chapter 1, Problem 41

Rank the following molecules by the length of the indicated bond from shortest to longest.
(a)
(b)
(c)

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Identify the type of bond in each molecule (e.g., single, double, or triple bond) and the atoms involved in the bond. Bond length is influenced by bond order and the size of the bonded atoms.

Recall that bond order is inversely proportional to bond length: triple bonds are shorter than double bonds, which are shorter than single bonds. Additionally, smaller atoms form shorter bonds compared to larger atoms.

Examine the periodic trends of the atoms involved in the bonds. For example, bonds involving smaller atoms (e.g., C-H) are shorter than those involving larger atoms (e.g., C-I).

Compare the bond types and the atomic sizes for the indicated bonds in each molecule. Rank the bonds based on their expected lengths, starting with the shortest (highest bond order and/or smallest atoms) and ending with the longest (lowest bond order and/or largest atoms).

Verify your ranking by considering any additional factors, such as resonance or hybridization, that might influence bond length. For example, resonance can lead to partial double-bond character, which shortens the bond compared to a pure single bond.

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Key Concepts

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

Bond Length

Bond length refers to the distance between the nuclei of two bonded atoms. It is influenced by factors such as atomic size, bond order, and the presence of lone pairs. Generally, shorter bonds are stronger due to greater overlap of atomic orbitals, while longer bonds tend to be weaker and more reactive.

Bond Order

Bond order is a measure of the number of chemical bonds between a pair of atoms. It is calculated as the difference between the number of bonding and antibonding electrons divided by two. Higher bond orders indicate stronger and shorter bonds, while lower bond orders correspond to weaker and longer bonds.

Electronegativity

Electronegativity is the tendency of an atom to attract electrons in a chemical bond. Differences in electronegativity between bonded atoms can affect bond length; for instance, bonds between atoms with similar electronegativities tend to be shorter and stronger. This concept is crucial for understanding the nature of bonds in different molecules.

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Related Practice

Textbook Question

The sulfur and oxygen in methanethiol and methanol are both sp³ hybridized. Why is the S―H bond longer than the O―H bond?

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Textbook Question

A molecular orbital diagram is shown for the C―Cl bond in chloromethane. If two more electrons were added to chloromethane, where would the electrons go?

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Textbook Question

How might electrons be excited from π to π* based on the molecular orbital diagram shown? [This will be relevant in Chapter 21.]

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Textbook Question

Use hybrid orbitals to draw the following molecules.

(c)

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Textbook Question

Use hybrid orbitals to draw the following molecules.