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Draw the structures of the compound that would give the spectral information below, and explain your reasoning. IR: 3300-3600, 2800-2950, 1710 cm 1 1H-NMR: 9.4 (1H, s), 3.4 (2H, t), 2.7 (1H broad s), 2.3 (2H, t)

Draw the structures of the compound that would give the spectral information below, and explain your reasoning. IR: 3300-3600, 2800-2950, 1710 cm 1 1H-NMR: 9.4 (1H, s), 3.4 (2H, t), 2.7 (1H broad s), 2.3 (2H, t)

Chemistry
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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**Title: Spectral Analysis and Structure Determination** **Objective:** Draw the structures of the compound that would give the following spectral information and explain your reasoning. **Spectral Data:** - **Infrared (IR) Spectroscopy:** - Peaks at 3300-3600 cm⁻¹ - Peaks at 2800-2950 cm⁻¹ - Peak at 1710 cm⁻¹ - **Proton Nuclear Magnetic Resonance (¹H-NMR) Spectroscopy:** - 9.4 ppm (1H, singlet, s) - 3.4 ppm (2H, triplet, t) - 2.7 ppm (1H, broad singlet, broad s) - 2.3 ppm (2H, triplet, t) **Explanation:** - **IR Spectroscopy:** - **3300-3600 cm⁻¹:** This range usually indicates the presence of an O-H group, such as alcohols or phenols. - **2800-2950 cm⁻¹:** This is characteristic of C-H stretching in alkanes. - **1710 cm⁻¹:** This peak is indicative of a carbonyl group (C=O), such as in aldehydes, ketones, or carboxylic acids. - **¹H-NMR Spectroscopy:** - **9.4 ppm (1H, s):** Suggests the presence of an aldehydic proton. - **3.4 ppm (2H, t):** Could indicate protons adjacent to a heteroatom or unsaturated system. - **2.7 ppm (1H, broad s):** May correspond to a proton involved in hydrogen bonding, possibly an O-H proton. - **2.3 ppm (2H, t):** Typically signals protons in a neighboring position to a carbonyl group. By examining these pieces of spectral information, the task is to propose a molecular structure that fits the given data. Consider how the molecular fragments indicated by the NMR and IR data might combine to form a coherent structure.
Transcribed Image Text:**Title: Spectral Analysis and Structure Determination** **Objective:** Draw the structures of the compound that would give the following spectral information and explain your reasoning. **Spectral Data:** - **Infrared (IR) Spectroscopy:** - Peaks at 3300-3600 cm⁻¹ - Peaks at 2800-2950 cm⁻¹ - Peak at 1710 cm⁻¹ - **Proton Nuclear Magnetic Resonance (¹H-NMR) Spectroscopy:** - 9.4 ppm (1H, singlet, s) - 3.4 ppm (2H, triplet, t) - 2.7 ppm (1H, broad singlet, broad s) - 2.3 ppm (2H, triplet, t) **Explanation:** - **IR Spectroscopy:** - **3300-3600 cm⁻¹:** This range usually indicates the presence of an O-H group, such as alcohols or phenols. - **2800-2950 cm⁻¹:** This is characteristic of C-H stretching in alkanes. - **1710 cm⁻¹:** This peak is indicative of a carbonyl group (C=O), such as in aldehydes, ketones, or carboxylic acids. - **¹H-NMR Spectroscopy:** - **9.4 ppm (1H, s):** Suggests the presence of an aldehydic proton. - **3.4 ppm (2H, t):** Could indicate protons adjacent to a heteroatom or unsaturated system. - **2.7 ppm (1H, broad s):** May correspond to a proton involved in hydrogen bonding, possibly an O-H proton. - **2.3 ppm (2H, t):** Typically signals protons in a neighboring position to a carbonyl group. By examining these pieces of spectral information, the task is to propose a molecular structure that fits the given data. Consider how the molecular fragments indicated by the NMR and IR data might combine to form a coherent structure.
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