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Ch.1 - Structure and Bonding
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh.1 - Structure and BondingProblem 52g
Chapter 1, Problem 52g

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. Lewis structure of acetic acid showing carbon, oxygen, and hydrogen atoms with bonds and lone pairs.

Verified step by step guidance
1
Draw the Lewis structure for acetic acid (CH3COOH). Start by arranging the atoms: the central carbon atom is bonded to a methyl group (CH3), a carbonyl oxygen (O), and a hydroxyl group (OH).
Identify the types of orbitals involved in bonding. The carbon-carbon and carbon-oxygen single bonds are formed by the overlap of sp3 hybrid orbitals from carbon with the s orbitals of hydrogen and the sp3 hybrid orbitals of oxygen. The carbon-oxygen double bond involves sp2 hybrid orbitals from carbon and oxygen, with a pi bond formed by the overlap of unhybridized p orbitals.
Determine the approximate bond angles. Around the central carbon atom, the bond angles are approximately 120 degrees due to the sp2 hybridization, which gives a trigonal planar geometry. Around the oxygen in the hydroxyl group, the bond angle is approximately 104.5 degrees due to the bent shape caused by the two lone pairs on oxygen.
Consider the resonance structures. Although acetic acid primarily exists in the form shown, resonance can occur between the carbonyl oxygen and the hydroxyl group, affecting the electron distribution.
Review the formal charges. Ensure that all atoms have a formal charge of zero, which is typical for stable organic molecules like acetic acid. This involves checking that each atom has the appropriate number of bonds and lone pairs to satisfy the octet rule.

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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 in a molecule and the lone pairs of electrons that may exist. They use dots to represent valence electrons and lines to represent bonds between atoms. Understanding how to draw Lewis structures is essential for visualizing molecular geometry and predicting reactivity.
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Orbital Hybridization

Orbital hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate the bonding requirements of atoms in a molecule. This process helps explain the geometry of molecular structures, as different types of hybridization (such as sp, sp2, and sp3) correspond to specific bond angles and shapes.
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Bond Angles

Bond angles are the angles formed between adjacent bonds in a molecule, which are influenced by the arrangement of electron pairs around a central atom. These angles are critical for determining the three-dimensional shape of a molecule, which can affect its physical and chemical properties. Common bond angles include 109.5° for tetrahedral, 120° for trigonal planar, and 180° for linear geometries.
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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

h.

655
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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.

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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.

b. [CH2OH]+

1040
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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

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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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