Inspect the two molecules and consider which compound contains the greater amount of gauche conformation for internal rotation about the central (blue) bond. H3C-CH2-O- -CH3 H3C-CH2-CH2-CH3 A В Select the best statement. For both compounds, the central atoms have identical substituents (methyl groups) that experience identical repulsive forces. Therefore, compounds A and B have the same amount of gauche conformation present. O The C-O bond is shorter than the C-C bond, so the methyl groups of the ether A are closer together, creating steric strain on the gauche conformation. This phenomenon results in less gauche conformation present for A, and hence more of the gauche conformation for butane B. O The electrons of the oxygen in the ether A take up about as much space as the hydrogens of the corresponding carbon of B, and there is very nearly the same amount of steric and electrostatic pressure on the methyl groups of both compounds A and B. Therefore, they have about the same amount of gauche conformation present. O The C-C bond is shorter than the C-O bond, so the methyl groups of butane B are closer together, creating steric strain on the gauche conformation. This phenomenon results in less gauche conformation present for butane B, and hence more of the gauche conformation for the ether A. The oxygen atom of the ether A does not have the hydrogen atoms that the corresponding carbon of butane B does, so there is less steric pressure in A, and hence, A has more of the gauche conformation present.
Inspect the two molecules and consider which compound contains the greater amount of gauche conformation for internal rotation about the central (blue) bond. H3C-CH2-O- -CH3 H3C-CH2-CH2-CH3 A В Select the best statement. For both compounds, the central atoms have identical substituents (methyl groups) that experience identical repulsive forces. Therefore, compounds A and B have the same amount of gauche conformation present. O The C-O bond is shorter than the C-C bond, so the methyl groups of the ether A are closer together, creating steric strain on the gauche conformation. This phenomenon results in less gauche conformation present for A, and hence more of the gauche conformation for butane B. O The electrons of the oxygen in the ether A take up about as much space as the hydrogens of the corresponding carbon of B, and there is very nearly the same amount of steric and electrostatic pressure on the methyl groups of both compounds A and B. Therefore, they have about the same amount of gauche conformation present. O The C-C bond is shorter than the C-O bond, so the methyl groups of butane B are closer together, creating steric strain on the gauche conformation. This phenomenon results in less gauche conformation present for butane B, and hence more of the gauche conformation for the ether A. The oxygen atom of the ether A does not have the hydrogen atoms that the corresponding carbon of butane B does, so there is less steric pressure in A, and hence, A has more of the gauche conformation present.
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:**Topic: Gauche Conformation in Organic Compounds**
**Overview:**
This section explores the gauche conformation of two molecules. Examine the internal rotation about the central (blue) bond in compounds A and B to determine which has a greater amount of gauche conformation.
**Molecular Structures:**
- **Compound A**: H₃C—CH₂—O—CH₃
- **Compound B**: H₃C—CH₂—CH₂—CH₃
**Question:**
Select the best statement regarding the gauche conformation in compounds A and B.
1. **Both compounds have identical central substituents** (methyl groups) with similar repulsive forces. Thus, compounds A and B have the same amount of gauche conformation.
2. **The C—O bond in ether A is shorter than the C—C bond,** causing the methyl groups in A to be closer and experience greater steric strain. This results in less gauche conformation for A, and more for butane B.
3. **The oxygen's electrons in ether A occupy space comparable to hydrogens in B,** causing similar steric and electrostatic pressure on methyl groups in A and B. Thus, both have similar gauche conformation amounts.
4. **The C—C bond is shorter than the C—O bond,** making the methyl groups in B closer, increasing steric strain. This leads to less gauche conformation in B, hence more for ether A.
5. **The oxygen atom in ether A lacks hydrogens found in butane B's corresponding carbon,** resulting in less steric pressure in A. Consequently, A has more gauche conformation.
**Analysis:**
- Compare the differences in bond lengths and resulting steric effects between oxygen and carbon atoms.
- Evaluate the spatial occupation and electrostatic interactions caused by substituents on the central atoms.
**Conclusion:**
Consider chemical interactions and structural differences to choose the most plausible statement about the gauche conformation of compounds A and B.
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