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Ch.8 - Covalent Compounds: Bonding Theories and Molecular Structure
Chapter 8, Problem 32b

The following ball-and-stick molecular model is a representation of acetaminophen, the active ingredient in such over-thecounter headache remedies as Tylenol. (Red = O, gray = C, blue = N, ivory = H.) (b) Indicate the positions of the multiple bonds in acetaminophen.

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Identify the atoms involved in multiple bonds: In acetaminophen, look for carbon (C) atoms that are double-bonded to oxygen (O) or nitrogen (N) atoms.
Examine the structure: Acetaminophen has a benzene ring, which contains alternating single and double bonds between carbon atoms.
Locate the carbonyl group: This is a common functional group in acetaminophen, consisting of a carbon atom double-bonded to an oxygen atom (C=O).
Identify the amide linkage: In acetaminophen, there is a nitrogen atom bonded to a carbonyl carbon, forming an amide group (N-C=O).
Mark the positions: Highlight the double bonds in the benzene ring and the carbonyl group in the acetaminophen structure.

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Key Concepts

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

Molecular Structure

Molecular structure refers to the arrangement of atoms within a molecule, including the types of bonds (single, double, or triple) and the spatial orientation of these atoms. Understanding the molecular structure of acetaminophen is crucial for identifying where multiple bonds are located, as it directly influences the molecule's chemical properties and reactivity.
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Types of Chemical Bonds

Chemical bonds are the forces that hold atoms together in a molecule. The main types include single bonds (one pair of electrons shared), double bonds (two pairs of electrons shared), and triple bonds (three pairs of electrons shared). In acetaminophen, recognizing the presence and position of double bonds is essential for accurately indicating the multiple bonds in the molecular model.
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Ball-and-Stick Model

The ball-and-stick model is a three-dimensional representation of molecules, where balls represent atoms and sticks represent the bonds between them. This model helps visualize the geometry of the molecule, including bond angles and lengths. In the case of acetaminophen, using this model allows for a clearer identification of the positions of multiple bonds within the structure.
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Related Practice
Textbook Question
The VSEPR model is a simple predictive tool that is usually,but not always, correct. Take urea, for instance, a wasteproduct excreted in animal urine:

What hybridization would you expect for the C and N atoms in urea according to the VSEPR model, and what approximate values would you expect for the various bond angles? What are the actual hybridizations and bond angles based on themolecular model shown? 1Red = O, gray = C, blue = N,ivory = H.2
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Textbook Question
The following ball-and-stick molecular model is a representationof acetaminophen, the active ingredient in such over-thecounterheadache remedies as Tylenol. 1Red = O, gray = C,blue = N, ivory = H.2(c) What is the geometry around each carbon?

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Textbook Question

The following ball-and-stick molecular model is a representation of acetaminophen, the active ingredient in such over-thecounter headache remedies as Tylenol. (Red = O, gray = C, blue = N, ivory = H.) (a) What is the formula of acetaminophen?

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Textbook Question

The following ball-and-stick molecular model is a representation of thalidomide, a drug that causes birth defects when taken by expectant mothers but is valuable for its use against leprosy. The lines indicate only the connections between atoms, not whether the bonds are single, double, or triple. 1Red = O, gray = C, blue = N, ivory = H.2 (a) What is the formula of thalidomide?

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Textbook Question

Ethyl acetate, CH3CO2CH2CH3, is commonly used as a solvent and nail-polish remover. Look at the following electrostatic potential map of ethyl acetate, and explain the observed polarity.

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Textbook Question

Two dichloroethylene molecules with the same chemical formula 1C2H2Cl22, but different arrangements of atoms are shown. (b) Which form of dichloroethylene has a dipole moment of 2.39 D, and which has a dipole moment of 0.00 D?

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