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

The following ball-and-stick molecular model is a representation of acetaminophen, the active ingredient in such over-thecounter headache remedies as Tylenol. 1Red = O, gray = C, blue = N, ivory = H.2 (c) What is the geometry around each carbon? Ball-and-stick model of acetaminophen showing molecular geometry with atoms color-coded.

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1
Identify the different types of carbon atoms in the acetaminophen molecule. There are carbons in the benzene ring and carbons in the functional groups attached to the ring.
For the carbons in the benzene ring, recognize that each carbon is bonded to three other atoms (two carbons and one hydrogen) and has a trigonal planar geometry with bond angles of approximately 120 degrees.
Examine the carbon attached to the hydroxyl group (OH). This carbon is bonded to three other atoms (one carbon, one oxygen, and one hydrogen) and also has a trigonal planar geometry.
Look at the carbon in the amide group (C=O). This carbon is bonded to three other atoms (one carbon, one oxygen, and one nitrogen) and has a trigonal planar geometry.
Summarize the geometries: All the carbons in the benzene ring and the carbons in the functional groups (hydroxyl and amide) exhibit trigonal planar geometry.

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Key Concepts

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

Molecular Geometry

Molecular geometry refers to the three-dimensional arrangement of atoms within a molecule. It is determined by the number of bonding pairs and lone pairs of electrons around the central atom, which influences the shape of the molecule. Understanding molecular geometry is crucial for predicting the physical and chemical properties of compounds, including reactivity and polarity.
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VSEPR Theory

Valence Shell Electron Pair Repulsion (VSEPR) theory is a model used to predict the geometry of individual molecules based on the repulsion between electron pairs in the valence shell of the central atom. According to VSEPR, electron pairs will arrange themselves to minimize repulsion, leading to specific molecular shapes such as linear, trigonal planar, tetrahedral, and more, depending on the number of bonding and non-bonding pairs.
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Hybridization

Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate the bonding pairs of electrons in a molecule. In carbon compounds, hybridization can lead to different geometries: sp3 hybridization results in tetrahedral geometry, sp2 leads to trigonal planar, and sp gives linear geometry. Understanding hybridization helps in predicting the bond angles and overall shape of the molecule.
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Related Practice
Textbook Question
What is the geometry around the central atom in each of the following molecular models? (a)

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Textbook Question

Three of the following molecular models have a tetrahedral central atom, and one does not. Which is the odd one? (There may be a 'hidden' atom directly behind a visible atom in some cases.) (a)

(b)

(c)

(d)

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Textbook Question
The VSEPR model is a simple predictive tool that is usually, but not always, correct. Take urea, for instance, a waste product 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 the molecular 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 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 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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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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