Textbook Question
Predict the hybridization and geometry of the carbon and nitrogen atoms in the following molecules and ions. (Hint: Resonance.)
d.
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Ch.1 - Structure and Bonding
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 1, Problem 52h
For each of the following compounds and ions,
1. Draw a Lewis structure.
2. Show the kinds of orbitals that overlap to form each bond.
3. Give approximate bond angles around each atom except hydrogen
h. 
Verified step by step guidance1
Identify the compound as furan-2(5H)-one, which is a five-membered lactone ring containing an oxygen atom and a carbonyl group.
Draw the Lewis structure by arranging the atoms in a ring with alternating single and double bonds, ensuring that each atom satisfies the octet rule. The oxygen in the carbonyl group will have a double bond with the adjacent carbon.
Determine the types of orbitals involved in bonding: the C-O single bond involves sp3 hybridized orbitals from carbon and oxygen, while the C=O double bond involves sp2 hybridized orbitals from carbon and oxygen.
Estimate the bond angles: around the sp2 hybridized carbon in the carbonyl group, the bond angles are approximately 120 degrees, while around the sp3 hybridized carbon, the bond angles are approximately 109.5 degrees.
Consider resonance structures: the double bond in the ring can shift, creating resonance structures that contribute to the stability of the molecule.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Lewis Structures
Lewis structures are diagrams that represent the bonding between atoms of a molecule and the lone pairs of electrons that may exist. They are essential for visualizing the arrangement of atoms, the distribution of electrons, and the types of bonds (single, double, or triple) present in a molecule. Understanding Lewis structures helps in predicting the geometry and reactivity of the molecule.
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Drawing the Lewis Structure for N2H4.
Orbital Overlap and Bond Formation
Orbital overlap is a concept that explains how covalent bonds form when atomic orbitals overlap, allowing electrons to be shared between atoms. The type of orbitals involved (s, p, d) determines the bond's characteristics. For example, sigma (σ) bonds result from head-on overlap, while pi (π) bonds result from side-on overlap. Recognizing the types of orbitals involved is crucial for understanding molecular geometry and bond strength.
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06:00Single bonds, double bonds, and triple bonds.
Bond Angles and Molecular Geometry
Bond angles are the angles between adjacent bonds at an atom, which are determined by the molecule's geometry. VSEPR (Valence Shell Electron Pair Repulsion) theory is often used to predict these angles, as electron pairs around a central atom will arrange themselves to minimize repulsion. Understanding bond angles is important for predicting the shape and reactivity of molecules, as well as their physical properties.
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Related Practice
Textbook Question
For each of the following compounds and ions,
1. Draw a Lewis structure.
2. Show the kinds of orbitals that overlap to form each bond.
3. Give approximate bond angles around each atom except hydrogen.
d. CH3–CH=CH2
e. HC≡C–CHO
f. H2N–CH2–CN
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Textbook Question
For each of the following compounds and ions,
1. Draw a Lewis structure.
2. Show the kinds of orbitals that overlap to form each bond.
3. Give approximate bond angles around each atom except hydrogen.
g.
9
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Textbook Question
Predict the hybridization and geometry of the carbon and nitrogen atoms in the following molecules and ions. (Hint: Resonance.)
a.
b.
c.
8
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Textbook Question
For each of the following compounds and ions,
1. Draw a Lewis structure.
2. Show the kinds of orbitals that overlap to form each bond.
3. Give approximate bond angles around each atom except hydrogen.
c. CH2=N–CH3
2
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Textbook Question
In most amines, the nitrogen atom is sp3 hybridized, with a pyramidal structure and bond angles close to 109°. In urea, both nitrogen atoms are found to be planar, with bond angles close to 120°. Explain this surprising finding. (Hint: Consider resonance forms and the overlap needed in them.)
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