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Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
All textbooksBruice 8th EditionCh. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)Problem 50b
Chapter 2, Problem 50b

Which of the following has a bond closest to the ionic end of the bond spectrum?
CH3NH2 CH3CH3 CH3F CH3OH

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1
Step 1: Understand the bond spectrum. The bond spectrum ranges from purely covalent bonds (equal sharing of electrons) to purely ionic bonds (complete transfer of electrons). Bonds closer to the ionic end of the spectrum have a significant difference in electronegativity between the bonded atoms.
Step 2: Identify the electronegativity of the atoms involved in each bond. Use the Pauling scale: Fluorine (F) has the highest electronegativity (3.98), followed by Oxygen (O, 3.44), Nitrogen (N, 3.04), Carbon (C, 2.55), and Hydrogen (H, 2.20).
Step 3: Analyze the bonds in each molecule: - CH3NH2: The C-N bond has a moderate electronegativity difference (2.55 for C and 3.04 for N). - CH3CH3: The C-C bond has no electronegativity difference (both are 2.55). - CH3F: The C-F bond has a large electronegativity difference (2.55 for C and 3.98 for F). - CH3OH: The C-O bond has a significant electronegativity difference (2.55 for C and 3.44 for O).
Step 4: Compare the electronegativity differences. The larger the difference, the closer the bond is to the ionic end of the spectrum. The C-F bond in CH3F has the largest electronegativity difference, making it the most polar bond among the options.
Step 5: Conclude that CH3F has the bond closest to the ionic end of the bond spectrum due to the significant electronegativity difference between Carbon and Fluorine.

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Key Concepts

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

Electronegativity

Electronegativity is a measure of an atom's ability to attract and hold onto electrons in a chemical bond. In organic chemistry, differences in electronegativity between bonded atoms can determine the bond's character, ranging from ionic to covalent. For example, in a bond between carbon and fluorine, fluorine's high electronegativity creates a polar covalent bond, while a bond between carbon and hydrogen is more nonpolar.
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Bond Polarity

Bond polarity refers to the distribution of electrical charge across a bond due to differences in electronegativity between the atoms involved. A bond is considered polar when one atom attracts the shared electrons more strongly, leading to a partial positive charge on one end and a partial negative charge on the other. The greater the difference in electronegativity, the more polar the bond becomes, approaching ionic character.
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Ionic vs. Covalent Bonds

Ionic bonds form when there is a complete transfer of electrons from one atom to another, typically between metals and nonmetals, resulting in charged ions. In contrast, covalent bonds involve the sharing of electrons between atoms. The bond character can be viewed as a spectrum, with purely ionic bonds at one end and purely covalent bonds at the other, with polar covalent bonds falling in between based on the electronegativity difference.
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Related Practice
Textbook Question

What is the hybridization of all the atoms (other than hydrogen) in each of the following?

What are the bond angles around each atom?

i. H3O+

j. H2C═O

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Textbook Question

If the dipole moment of CH3F is 1.847 D and the dipole moment of CD3F is 1.858 D, which is more electronegative: hydrogen or deuterium?

Textbook Question

Draw the condensed structure of a compound that contains only carbon and hydrogen atoms and that has

a. three sp3 hybridized carbons.

b. one sp3 hybridized carbon and two sp2 hybridized carbons.

c. two sp3 hybridized carbons and two sp hybridized carbons.

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Textbook Question

Which of the following has a polar covalent bond?

CH3NH2 CH3CH3 CH3F CH3OH

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Textbook Question

What is the hybridization of all the atoms (other than hydrogen) in each of the following?

What are the bond angles around each atom?

c. -CH3

d. ⋅CH3

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Textbook Question

Account for the difference in the shape and color of the potential maps for ammonia and the ammonium ion in Section 1.11.

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