**Educational Content: Analyzing a ^1H-NMR Spectrum****Task Overview:**1. **Objective:** Propose a molecular structure with the formula $ C_{13}H_{18}O_2 $ based on the given ^1H-NMR spectrum.2. **Instructions:** Draw the structure in the provided box and label each hydrogen atom using the corresponding labels (a, b, c, etc.). Note that the TMS peak at 0 ppm is not part of the structure. 3. **Hints:** Consider that the mass spectrometry (MS) of this molecule shows major fragment peaks at m/z = 57 and 73. Calculate the index of hydrogen deficiency (IHD) for the molecular formula.**^1H-NMR Spectrum Details:**- **a:** Broad singlet for 1H at around 11 ppm.- **b:** Doublet for 2H at approximately 7.3 ppm.- **c:** Doublet for 2H at approximately 7.2 ppm.- **d:** Quartet for 1H at around 4.3 ppm.- **e:** Doublet for 2H around 3.9 ppm.- **f:** Multiplet for 1H around 2.7 ppm.- **g:** Doublet for 3H at about 1.2 ppm.- **h:** Doublet for 6H at approximately 0.9 ppm.- **TMS (Tetramethylsilane):** Peak at 0 ppm, not part of the molecule.*Note:* The spectrum reflects the number of unique hydrogen environments and their splitting patterns, which aid in identifying the molecular structure.---**Graph Description:**The horizontal axis represents the chemical shift in parts per million (ppm), which indicates the environment of the hydrogen atoms within the molecule. The vertical axis represents the signal intensity, correlating to the number of protons contributing to each peak. Peaks are labeled as described above, showing different splitting patterns such as singlets, doublets, quartets, and multiplets that correspond to the chemical environment surrounding each type of hydrogen atom.

1H NMR spectroscopy is useful to determine types of protons, their signals, splitting etc and hence we can determine structure of organic compounds.The chemical shift value of proton depends on chemical environment of proton. Hybridization, electronegativity of attached atom, magnetic anisotropy are the factors which affect the chemical shift value of proton.If electron donating group is attached then it increases electron density around the nucleus and makes that proton shielded. Shielded protons give lower chemical shift value.If electron withdrawing group is present then it decreases electron density around the nucleus and makes that proton deshielded. The deshielded proton gives higher chemical shift value.The splitting pattern of signal can be determined by using n+1 rule. Where n is the number of neighbouring protons.Internsity of the signal can be determined by Pascal's triangle.Molecular formula:- C13H18O2The degree of unsaturation or index of hydrogen deficiency can be determined asDOU greater than or equal to 4 indicates the presence of a benzene ring in a structure.Where C, H, X, and N are the number of carbon, hydrogen, halogen, and nitrogen atoms respectively.0.9 ppm, 6H, d:- This signal indicates two equivalent methyl groups attached to the CH group. Thus possible fragment is CH3-CH-CH31.5 ppm, 3H, d:- This signal indicates the fragment CH-CH31.9 ppm, 1H, m:- This signal indicates one proton has a number of neighboring hydrogen.2.5 ppm, 2H, d:- This signal indicates fragment -CH2-CH-3.6 ppm, 1H, q:- The higher chemical shift value indicates this proton is deshielded due electronegativity effect of the electron withdrawing group. The possible fragment is X-CH-CH37.2 ppm, 2H, d: These are protons of the aromatic ring, highly deshielded due magnetic anisotropic effect of the aromatic ring.7.4 ppm, 2H, d:- These are protons of the aromatic ring, highly deshielded due magnetic anisotropic effect of the aromatic ring.These two signals indicate para di-substituted benzene ring.12 ppm, 1H, broad:-Proton attached to the oxygen of carboxylic group (-COOH) shows broad peak and chemical shift value in the range 11.5-15.5 ppm. Thus possible fragment -COOHFrom the data, it is clear that Unknown contains -COOH group, para-di-substituted benzene ring, and other fragments.By considering all the points probable structure for the given data is The structure for given data is

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4. Propose a structure (Lewis structure okay) with molecular formula C13H18O2 that is consistent with ¹H-NMR spectrum below. Place your structure in the box and label each hydrogen atom using corresponding labels given in the spectrum (a, b, c, etc.). Note that the peak labeled "TMS" at 0 ppr not part of your proposed structure and should not be included. Hints: the MS of this molecule major fragment peaks at m/z = 57 and 73; calculate the IHD for the given molecular formula. $60 abrary ty 035 09 03 3.75 07 190 90 950 so TO TO SED FO STO 015 02 to 500 4. Draw structure and label hydrogen atoms a br s 1H 105 13 b d 2H с d 2H pom d q 1H e d 2H g d 3H f m 1H i h d 6H TMS

4. Propose a structure (Lewis structure okay) with molecular formula C13H18O2 that is consistent with ¹H-NMR spectrum below. Place your structure in the box and label each hydrogen atom using corresponding labels given in the spectrum (a, b, c, etc.). Note that the peak labeled "TMS" at 0 ppr not part of your proposed structure and should not be included. Hints: the MS of this molecule major fragment peaks at m/z = 57 and 73; calculate the IHD for the given molecular formula. $60 abrary ty 035 09 03 3.75 07 190 90 950 so TO TO SED FO STO 015 02 to 500 4. Draw structure and label hydrogen atoms a br s 1H 105 13 b d 2H с d 2H pom d q 1H e d 2H g d 3H f m 1H i h d 6H TMS

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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Concept explainers

Mass Spectrometry

This process is an instrumental method in which a sample is changed to fast moving positive ions by electron bombardment. The charged particles vary due to their different mass to charge ratio and are estimated with the help of this difference. It is also called mass spectroscopy.

Question

**Educational Content: Analyzing a ^1H-NMR Spectrum**

**Task Overview:**

1. **Objective:** Propose a molecular structure with the formula $ C_{13}H_{18}O_2 $ based on the given ^1H-NMR spectrum.
2. **Instructions:** Draw the structure in the provided box and label each hydrogen atom using the corresponding labels (a, b, c, etc.). Note that the TMS peak at 0 ppm is not part of the structure.
3. **Hints:** Consider that the mass spectrometry (MS) of this molecule shows major fragment peaks at m/z = 57 and 73. Calculate the index of hydrogen deficiency (IHD) for the molecular formula.

**^1H-NMR Spectrum Details:**

- **a:** Broad singlet for 1H at around 11 ppm.
- **b:** Doublet for 2H at approximately 7.3 ppm.
- **c:** Doublet for 2H at approximately 7.2 ppm.
- **d:** Quartet for 1H at around 4.3 ppm.
- **e:** Doublet for 2H around 3.9 ppm.
- **f:** Multiplet for 1H around 2.7 ppm.
- **g:** Doublet for 3H at about 1.2 ppm.
- **h:** Doublet for 6H at approximately 0.9 ppm.
- **TMS (Tetramethylsilane):** Peak at 0 ppm, not part of the molecule.

*Note:* The spectrum reflects the number of unique hydrogen environments and their splitting patterns, which aid in identifying the molecular structure.

---

**Graph Description:**

The horizontal axis represents the chemical shift in parts per million (ppm), which indicates the environment of the hydrogen atoms within the molecule. The vertical axis represents the signal intensity, correlating to the number of protons contributing to each peak. Peaks are labeled as described above, showing different splitting patterns such as singlets, doublets, quartets, and multiplets that correspond to the chemical environment surrounding each type of hydrogen atom.

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Step 1: NMR spectroscopy

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Step 2: Splitting pattern and intensity

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Step 3: Molecular formula and Degree of unsaturation

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Step 4: Analysis of NMR data

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Step 5: Determine structure of unknown

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Step 6: Assignment of signals

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