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
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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
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 8

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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