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Below are the NMR spectra and molecular formulas of three molecules. Draw the complete structure in the boxes below. All the atoms in each molecule are closed shell (octets) and uncharged. Lack of IR data does not mean that a specific functional group is not present in the molecule. a) C11H1402 (There is a C=0 stretch in the IR of the compound)

Below are the NMR spectra and molecular formulas of three molecules. Draw the complete structure in the boxes below. All the atoms in each molecule are closed shell (octets) and uncharged. Lack of IR data does not mean that a specific functional group is not present in the molecule. a) C11H1402 (There is a C=0 stretch in the IR of the compound)

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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**Table 13.3: Correlation of ¹H Chemical Shift with Environment** This table presents the chemical shift values (δ) in proton NMR spectroscopy associated with different types of hydrogens in various environments. The data is organized into two main columns, each listing different hydrogen types and their corresponding chemical shift ranges. ### Left Column: - **Reference:** - Structure: (CH₃)₄Si - Chemical shift (δ): 0 - **Saturated Primary:** - Structure: —CH₃ - Chemical shift (δ): 0.7–1.3 - **Saturated Secondary:** - Structure: —CH₂— - Chemical shift (δ): 1.2–1.6 - **Saturated Tertiary:** - Structure: —CH— - Chemical shift (δ): 1.4–1.8 - **Allylic:** - Structure: =C—CH– - Chemical shift (δ): 1.6–2.2 - **Methyl Ketone:** - Structure: O=C—CH₃ - Chemical shift (δ): 2.0–2.4 - **Aromatic Methyl:** - Structure: Ar—CH₃ - Chemical shift (δ): 2.4–2.7 - **Alkynyl:** - Structure: ≡C—H - Chemical shift (δ): 2.5–3.0 ### Right Column: - **Alkyl Halide:** - Structure: C—(Cl, Br, I)—H - Chemical shift (δ): 2.5–4.0 - **Alcohol:** - Structure: C—OH - Chemical shift (δ): 2.5–5.0 (Variable) - **Alcohol, Ether:** - Structure: C—O—C—H - Chemical shift (δ): 3.3–4.5 - **Vinylic:** - Structure: C=C—H - Chemical shift (δ): 4.5–6.5 - **Aromatic:** - Structure: Ar—H - Chemical shift (δ): 6.5–8.0 -
Transcribed Image Text:**Table 13.3: Correlation of ¹H Chemical Shift with Environment** This table presents the chemical shift values (δ) in proton NMR spectroscopy associated with different types of hydrogens in various environments. The data is organized into two main columns, each listing different hydrogen types and their corresponding chemical shift ranges. ### Left Column: - **Reference:** - Structure: (CH₃)₄Si - Chemical shift (δ): 0 - **Saturated Primary:** - Structure: —CH₃ - Chemical shift (δ): 0.7–1.3 - **Saturated Secondary:** - Structure: —CH₂— - Chemical shift (δ): 1.2–1.6 - **Saturated Tertiary:** - Structure: —CH— - Chemical shift (δ): 1.4–1.8 - **Allylic:** - Structure: =C—CH– - Chemical shift (δ): 1.6–2.2 - **Methyl Ketone:** - Structure: O=C—CH₃ - Chemical shift (δ): 2.0–2.4 - **Aromatic Methyl:** - Structure: Ar—CH₃ - Chemical shift (δ): 2.4–2.7 - **Alkynyl:** - Structure: ≡C—H - Chemical shift (δ): 2.5–3.0 ### Right Column: - **Alkyl Halide:** - Structure: C—(Cl, Br, I)—H - Chemical shift (δ): 2.5–4.0 - **Alcohol:** - Structure: C—OH - Chemical shift (δ): 2.5–5.0 (Variable) - **Alcohol, Ether:** - Structure: C—O—C—H - Chemical shift (δ): 3.3–4.5 - **Vinylic:** - Structure: C=C—H - Chemical shift (δ): 4.5–6.5 - **Aromatic:** - Structure: Ar—H - Chemical shift (δ): 6.5–8.0 -
**Educational Content on NMR Spectra and Molecular Structure** **Introduction** In this educational module, we will explore the use of nuclear magnetic resonance (NMR) spectroscopy to deduce the structure of organic molecules. The goal is to understand the relationship between NMR spectra and chemical structure by analyzing the given data for three compounds. **NMR Spectrum Analysis** The NMR spectrum provided corresponds to a molecule with the molecular formula C₁₁H₁₄O₂. It is important to note the presence of a C=O stretch identified in the IR spectrum of this compound, suggesting the presence of a carbonyl group. **Spectrum Details:** - **Chemical Shift (PPM):** The x-axis represents the chemical shift in parts per million (PPM). - **Splitting Patterns:** - At around 7 PPM: There are two doublets (d), each integrating to 2H, indicating the presence of aromatic protons, likely part of a benzene ring. - At around 4.2 PPM: A triplet (t) integrating to 2H, suggests the presence of a -CH₂- group next to an oxygen atom, possibly part of an ester or ether. - At around 2.5 PPM: Another triplet (t) integrating to 2H, typically indicates a -CH₂- group adjacent to a carbonyl or another electron-withdrawing group. - At around 1.2 PPM: A singlet (s) integrating to 3H, likely represents a methyl group not adjacent to a highly electronegative atom or aromatic system. - At around 1 PPM: Another singlet (s) integrating to 3H, also indicative of a methyl group in a similar environment. **Structural Deduction:** Given the spectra, draw the complete structure of the compound in the provided box. Consider the cues from the splitting patterns and chemical shifts to incorporate functional groups like aromatic rings, carbonyls, ethers, and esters appropriately. **Conclusion** The exercise demonstrates how NMR and IR spectroscopy provide complementary information that aids in the structural elucidation of organic compounds. By understanding these data, chemists can deduce the presence of different functional groups and the overall structure of the molecule. **Further Instructions:** Use the given molecular formula and spectral data to deduce a possible structure in the box labeled "Draw the structure of the compound."
Transcribed Image Text:**Educational Content on NMR Spectra and Molecular Structure** **Introduction** In this educational module, we will explore the use of nuclear magnetic resonance (NMR) spectroscopy to deduce the structure of organic molecules. The goal is to understand the relationship between NMR spectra and chemical structure by analyzing the given data for three compounds. **NMR Spectrum Analysis** The NMR spectrum provided corresponds to a molecule with the molecular formula C₁₁H₁₄O₂. It is important to note the presence of a C=O stretch identified in the IR spectrum of this compound, suggesting the presence of a carbonyl group. **Spectrum Details:** - **Chemical Shift (PPM):** The x-axis represents the chemical shift in parts per million (PPM). - **Splitting Patterns:** - At around 7 PPM: There are two doublets (d), each integrating to 2H, indicating the presence of aromatic protons, likely part of a benzene ring. - At around 4.2 PPM: A triplet (t) integrating to 2H, suggests the presence of a -CH₂- group next to an oxygen atom, possibly part of an ester or ether. - At around 2.5 PPM: Another triplet (t) integrating to 2H, typically indicates a -CH₂- group adjacent to a carbonyl or another electron-withdrawing group. - At around 1.2 PPM: A singlet (s) integrating to 3H, likely represents a methyl group not adjacent to a highly electronegative atom or aromatic system. - At around 1 PPM: Another singlet (s) integrating to 3H, also indicative of a methyl group in a similar environment. **Structural Deduction:** Given the spectra, draw the complete structure of the compound in the provided box. Consider the cues from the splitting patterns and chemical shifts to incorporate functional groups like aromatic rings, carbonyls, ethers, and esters appropriately. **Conclusion** The exercise demonstrates how NMR and IR spectroscopy provide complementary information that aids in the structural elucidation of organic compounds. By understanding these data, chemists can deduce the presence of different functional groups and the overall structure of the molecule. **Further Instructions:** Use the given molecular formula and spectral data to deduce a possible structure in the box labeled "Draw the structure of the compound."
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