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 50c
Cyclopropane (C3H6, a three-membered ring) is more reactive than most other cycloalkanes.
c. Suggest why cyclopropane is so reactive.
Verified step by step guidance1
Cyclopropane is a three-membered ring, which means it has significant angle strain. The ideal bond angle for sp3 hybridized carbon atoms is 109.5 degrees, but in cyclopropane, the bond angles are approximately 60 degrees.
The deviation from the ideal bond angle creates angle strain, which increases the potential energy of the molecule, making it less stable and more reactive.
In addition to angle strain, cyclopropane also experiences torsional strain due to the eclipsing interactions of the hydrogen atoms attached to the carbon atoms in the ring.
The combination of angle strain and torsional strain makes cyclopropane more reactive as the molecule seeks to relieve this strain by undergoing chemical reactions.
Cyclopropane can participate in reactions such as ring-opening reactions, where the strain is relieved by breaking one of the carbon-carbon bonds, leading to more stable, open-chain structures.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ring Strain
Cyclopropane experiences significant ring strain due to its three-membered ring structure. The bond angles in cyclopropane are approximately 60 degrees, much smaller than the ideal tetrahedral angle of 109.5 degrees, causing increased angle strain. This strain makes the molecule less stable and more reactive as it seeks to relieve the strain.
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Bonding in Cycloalkanes
In cycloalkanes, the carbon atoms are typically sp3 hybridized, forming sigma bonds. However, in cyclopropane, the overlap of orbitals is less effective due to the ring's small size, leading to weaker bonds. This weaker bonding contributes to the molecule's higher reactivity compared to larger, more stable cycloalkanes.
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Torsional Strain
Cyclopropane also experiences torsional strain due to the eclipsing of hydrogen atoms attached to the carbon atoms. This eclipsing increases the energy of the molecule, making it more reactive. The combination of torsional and angle strain in cyclopropane results in a highly strained and reactive structure.
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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.
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.
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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
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
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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