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10. The proton NMR of a compound has the following peaks. Which compound below best fits the data?

10. The proton NMR of a compound has the following peaks. Which compound below best fits the data?

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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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**Question 10:** The proton NMR of a compound has the following peaks. Which compound below best fits the data? **Structures:** - **A:** A benzene ring with an OCH₂CH₂Cl group and an NO₂ group attached. - **B:** A benzene ring with an OH and a CH-CH₃ (ethyl) group attached. - **C:** A benzene ring with a CH₂CH₂OH group and a Cl atom attached. - **D:** A benzene ring with a CH₂CH₂OH group and a Cl atom attached. **NMR Data:** - Broad singlet at δ 5.17 (1H) - Doublet at δ 1.49 (3H) - Quartet at δ 5.00 (1H) - Doublet at δ 7.22 (2H) - Doublet at δ 7.38 (2H) **Analysis:** To identify the correct structure corresponding to the NMR data provided: 1. **Broad Singlet at δ 5.17 (1H):** - Indicates a hydroxyl (OH) proton or similar. 2. **Doublet at δ 1.49 (3H):** - Suggests a methyl group (CH₃) adjacent to another proton group, such as in an ethyl group (CH-CH₃). 3. **Quartet at δ 5.00 (1H):** - Typical for a methine (CH) group in an ethyl group. 4. **Doublets at δ 7.22 (2H) and δ 7.38 (2H):** - Indicate aromatic protons, possibly on a substituted benzene ring. Consider these data points to identify the most likely structure based on the NMR information.
Transcribed Image Text:**Question 10:** The proton NMR of a compound has the following peaks. Which compound below best fits the data? **Structures:** - **A:** A benzene ring with an OCH₂CH₂Cl group and an NO₂ group attached. - **B:** A benzene ring with an OH and a CH-CH₃ (ethyl) group attached. - **C:** A benzene ring with a CH₂CH₂OH group and a Cl atom attached. - **D:** A benzene ring with a CH₂CH₂OH group and a Cl atom attached. **NMR Data:** - Broad singlet at δ 5.17 (1H) - Doublet at δ 1.49 (3H) - Quartet at δ 5.00 (1H) - Doublet at δ 7.22 (2H) - Doublet at δ 7.38 (2H) **Analysis:** To identify the correct structure corresponding to the NMR data provided: 1. **Broad Singlet at δ 5.17 (1H):** - Indicates a hydroxyl (OH) proton or similar. 2. **Doublet at δ 1.49 (3H):** - Suggests a methyl group (CH₃) adjacent to another proton group, such as in an ethyl group (CH-CH₃). 3. **Quartet at δ 5.00 (1H):** - Typical for a methine (CH) group in an ethyl group. 4. **Doublets at δ 7.22 (2H) and δ 7.38 (2H):** - Indicate aromatic protons, possibly on a substituted benzene ring. Consider these data points to identify the most likely structure based on the NMR information.
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