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Ch.8 - Covalent Compounds: Bonding Theories and Molecular Structure
Chapter 8, Problem 7

The connections between atoms in the amino acid histidine areshown. Complete the electron-dot structure by adding multiplebonds and lone pairs of electrons. Give the hybridization on thenumbered carbon and nitrogen atoms. (LO 8.4)Electron-dot structure of histidine showing atom connections and hybridization details.
(a) N1 = sp2, N2 = sp, C1 = sp2, C2 = sp3 (b) N1 = sp2, N2 = sp2, C1 = sp3, C2 = sp2 (c) N1 = sp3, N2 = sp, C1 = sp2, C2 = sp3 (d) N1 = sp3, N2 = sp2, C1 = sp2, C2 = sp3

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1
Identify the number of electron domains (bonds and lone pairs) around each atom to determine the hybridization.
For N1, count the number of sigma bonds and lone pairs to determine if it is sp, sp2, or sp3 hybridized.
For N2, count the number of sigma bonds and lone pairs to determine if it is sp, sp2, or sp3 hybridized.
For C1, count the number of sigma bonds and lone pairs to determine if it is sp, sp2, or sp3 hybridized.
For C2, count the number of sigma bonds and lone pairs to determine if it is sp, sp2, or sp3 hybridized.

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Key Concepts

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

Electron-Dot Structures

Electron-dot structures, or Lewis structures, represent the valence electrons of atoms within a molecule. They illustrate how atoms are bonded together and show lone pairs of electrons. In the context of amino acids like histidine, these structures help visualize the connectivity and bonding, including single, double, or triple bonds, which are crucial for understanding molecular geometry and reactivity.
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Hybridization

Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate bonding. The type of hybridization (sp, sp2, sp3) depends on the number of bonds and lone pairs around a central atom. For example, sp hybridization indicates a linear arrangement with two regions of electron density, while sp3 indicates a tetrahedral arrangement with four regions, which is essential for determining the geometry of molecules like histidine.
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Amino Acid Structure

Amino acids are organic compounds that serve as the building blocks of proteins. Each amino acid has a central carbon atom bonded to an amino group, a carboxyl group, a hydrogen atom, and a variable R group. The specific structure of amino acids, including functional groups and their connectivity, influences their chemical properties and interactions, which is critical for understanding biochemical processes and protein synthesis.
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Related Practice
Textbook Question
Give the geometry and approximate bond angles around thecentral atom in CCl3-. (LO 8.1)(a) Trigonal planar, 120°(b) Trigonal pyramidal, 109.5°(c) Trigonal pyramidal, 120°(d) Bent, 109.5°
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Textbook Question
The following diagrams illustrate p-p orbital overlap or s-porbital overlap. Which diagram represents a p bond in valencebond theory? (LO 8.3)(a)

(b)

(c)

(d)

656
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Textbook Question
Which of the following molecules has a central atom with sp3 hybridization? (LO 8.4) (a) PCl5 (b) OF2 (c) CO2 (d) SF4
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Textbook Question
Use the chemical structure for Tagamet, a drug used to treatpeptic ulcers and heartburn, to answer questions 8 and 9.

Which orbitals overlap to form bond 1? (LO 8.5)(a) s bond: N 1sp22 with C 1sp22; p bond: N (p) with C (p)(b) N 1sp22 with C 1sp22(c) s bond: N 1sp22 with C 1sp22; p bond: N 1sp22 withC 1sp22(d) s bond: N (sp) with C 1sp22; p bond: N (p) with C (p)
471
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Textbook Question
Use the chemical structure for Tagamet, a drug used to treat peptic ulcers and heartburn, to answer questions 8 and 9.

Which orbitals overlap to form bond 2? (LO 8.5) (a) C (sp) with C (sp) (b) C (sp) with C 1sp22 (c) C 1sp22 with C 1sp22 (d) C 1sp32 with C 1sp22
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Textbook Question
The C2 molecule has a MO diagram similar to N2 (Figure 8.22a). What is the bond order of C2 and is it paramagnetic or diamagnetic? (LO 8.12) (a) Bond order = 2, diamagnetic (b) Bond order = 2, paramagnetic (c) Bond order = 0, paramagnetic (d) Bond order = 3>2, diamagnetic
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