5. Determine the structure of the compound with the chemical formula shown below, based on the given spectrum. Be sure to show your work using or reproducing the table below. 3H A E 3H 5H B 1H 2H 8 6. 5 4 PPM 3 2
5. Determine the structure of the compound with the chemical formula shown below, based on the given spectrum. Be sure to show your work using or reproducing the table below. 3H A E 3H 5H B 1H 2H 8 6. 5 4 PPM 3 2
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

Transcribed Image Text:The image depicts a problem from a spectroscopy exercise aimed at determining the structure of a compound with the chemical formula \( \text{C}_{10}\text{H}_{14}\text{O} \) based on a given NMR spectrum. The exercise requires filling out a table and identifying the final structure.
### NMR Spectrum Analysis:
The spectrum displays peaks at various chemical shifts, each labeled with a signal (A through E), integration values, and splitting patterns.
#### Key Features:
- **Signal A:**
- Integration: 3H
- **Signal B:**
- Integration: 2H
- **Signal C:**
- Integration: 3H
- **Signal D:**
- Integration: 1H
- **Signal E:**
- Integration: 5H
#### Chemical Shift (PPM):
- A: Close to 1.0
- B: Around 1.5
- C: Near 2.0
- D: Approximately 4.0
- E: About 7.0
### Table Format:
Below is a template for students to fill in based on the spectrum analysis:
| Signal | Integration | Chemical Shift | Splitting | Possible Fragment |
|--------|-------------|----------------|-----------|-------------------|
| A | 3H | | | |
| B | 2H | | | |
| C | 3H | | | |
| D | 1H | | | |
| E | 5H | | | |
### Final Structure:
The task concludes with deducing the final chemical structure of the compound, using the information from the table and the spectrum.
This exercise helps students apply their understanding of NMR spectroscopy in practical scenarios, encouraging critical thinking and problem-solving in organic chemistry.
Expert Solution

Step 1: Explanation
For the interpretation of 1H NMR spectra, few basic points you should remember.
- More electronegative atom attached - proton get deshielded - has high value of chemical shift.
- More electropositive atom or normal carbon atom- protons get shielded - less chemical shift value.
- Aromatic protons falls in the range of 6-8 ppm.
- Normal alkane type protons falls in the range of 0.5 - 4.0 ppm depending upon the atom attached near to them.
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