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.
a. [NH2]–
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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 50a,b
Cyclopropane (C3H6, a three-membered ring) is more reactive than most other cycloalkanes.
a. Draw a Lewis structure for cyclopropane.
b. Compare the bond angles of the carbon atoms in cyclopropane with those in an acyclic (noncyclic) alkane.
Verified step by step guidance1
To draw the Lewis structure for cyclopropane (C3H6), start by arranging three carbon atoms in a triangular shape to represent the three-membered ring. Each carbon atom forms two single bonds with the adjacent carbon atoms.
Next, add hydrogen atoms. Each carbon atom in cyclopropane should be bonded to two hydrogen atoms to satisfy the tetravalency of carbon, resulting in each carbon having four bonds in total.
Now, compare the bond angles in cyclopropane. In an ideal acyclic alkane, the bond angles around each carbon atom are approximately 109.5 degrees, which is the tetrahedral angle.
In cyclopropane, the bond angles are significantly smaller due to the constraints of the three-membered ring. The bond angles in cyclopropane are approximately 60 degrees, which is much less than the ideal tetrahedral angle.
This deviation from the ideal bond angle introduces angle strain in cyclopropane, making it more reactive than acyclic alkanes or larger cycloalkanes with less angle strain.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Lewis Structure
A Lewis structure is a diagrammatic representation of a molecule showing how the valence electrons are arranged among the atoms in the molecule. For cyclopropane, the Lewis structure illustrates the three carbon atoms forming a triangle, each bonded to two hydrogen atoms, highlighting the shared electron pairs and the overall connectivity of the atoms.
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Bond Angles in Cycloalkanes
Bond angles in cycloalkanes are determined by the geometric arrangement of the carbon atoms. In cyclopropane, the bond angles are approximately 60 degrees due to the triangular shape, which is significantly smaller than the typical tetrahedral angle of 109.5 degrees found in acyclic alkanes. This deviation from the ideal angle introduces angle strain, contributing to cyclopropane's reactivity.
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Angle Strain
Angle strain occurs when bond angles deviate from their ideal values, causing increased energy and instability in a molecule. In cyclopropane, the 60-degree bond angles are much smaller than the ideal 109.5 degrees, leading to significant angle strain. This strain makes cyclopropane more reactive compared to larger cycloalkanes, which have bond angles closer to the ideal tetrahedral angle.
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Related Practice
Textbook Question
In 1934, Edward A. Doisy of Washington University extracted 3000 lb of hog ovaries to isolate a few milligrams of pure estradiol, a potent female hormone. Doisy burned 5.00 mg of this precious sample in oxygen and found that 14.54 mg of CO2 and 3.97 mg of H2O were generated.
b. The molecular weight of estradiol was later determined to be 272. Determine the molecular formula of estradiol.
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Textbook Question
Cyclopropane (C3H6, a three-membered ring) is more reactive than most other cycloalkanes.
c. Suggest why cyclopropane is so reactive.
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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]+
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Textbook Question
In 1934, Edward A. Doisy of Washington University extracted 3000 lb of hog ovaries to isolate a few milligrams of pure estradiol, a potent female hormone. Doisy burned 5.00 mg of this precious sample in oxygen and found that 14.54 mg of CO2 and 3.97 mg of H2O were generated.
a. Determine the empirical formula of estradiol.
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Textbook Question
If the carbon atom in CH2Cl2 were flat, there would be two stereoisomers. The carbon atom in CH2Cl2 is actually tetrahedral. Make a model of this compound, and determine whether there are any stereoisomers of CH2Cl2.
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