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Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
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All textbooksMullins 1st EditionCh. 15 - Structural Identification II: Nuclear Magnetic Resonance SpectroscopyProblem 63b
Chapter 14, Problem 63b

Complete the table of ¹H NMR data you'd generate for each of the following molecules.
(b) Chemical structure of ethyl isopropyl ether, showing an oxygen atom bonded to an ethyl and isopropyl group.

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1
Identify the structure of the molecule in question. Determine the number of unique hydrogen environments present in the molecule. Each unique environment will correspond to a different signal in the ¹H NMR spectrum.
For each unique hydrogen environment, determine the chemical shift. The chemical shift is influenced by the electronic environment around the hydrogen atoms, such as the presence of electronegative atoms or π-bonds. Use typical chemical shift ranges to estimate the values.
Determine the splitting pattern for each signal. The splitting pattern is determined by the number of neighboring hydrogens (n) using the n+1 rule, where n is the number of adjacent hydrogens.
Calculate the integration for each signal. The integration corresponds to the relative number of hydrogens contributing to each signal. This is typically represented as a ratio that reflects the number of hydrogens in each environment.
Compile the data into a table format, listing each unique hydrogen environment, its chemical shift, splitting pattern, and integration. This will provide a comprehensive overview of the ¹H NMR data for the molecule.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

¹H NMR Spectroscopy

¹H NMR (Proton Nuclear Magnetic Resonance) spectroscopy is a technique used to determine the structure of organic compounds by analyzing the magnetic environment of hydrogen atoms. It provides information about the number of hydrogen atoms, their chemical environment, and how they are connected within a molecule. The resulting spectrum displays peaks corresponding to different hydrogen environments, which can be interpreted to deduce structural information.
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Chemical Shift

Chemical shift in ¹H NMR refers to the position of the NMR signal relative to a standard reference compound, typically tetramethylsilane (TMS). It is measured in parts per million (ppm) and indicates the electronic environment surrounding a hydrogen atom. Factors such as electronegativity of nearby atoms and hybridization affect the chemical shift, helping to identify functional groups and structural features in a molecule.
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Spin-Spin Coupling

Spin-spin coupling, also known as J-coupling, occurs when non-equivalent hydrogen atoms influence each other's magnetic environment, causing splitting of NMR signals into multiplets. The pattern and number of peaks in a multiplet provide information about the number of neighboring hydrogen atoms (n+1 rule) and their spatial relationship. This coupling helps elucidate the connectivity and arrangement of atoms within a molecule.
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Related Practice
Textbook Question

For the hydrogen(s) screened in blue, draw the signal you would expect to see in a ¹H NMR spectrum. At which chemical shift would the signal appear?

(c)

1046
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Textbook Question

Complete the table of ¹H NMR data you'd generate for each of the following molecules.

(d)

1035
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Textbook Question

Draw the signal for the following multiplicities. What is the ratio of peaks within each signal?

(f) septet

930
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Textbook Question

Draw the ¹H NMR spectrum you would expect to see for each of the molecules in Assessment 15.63.

(b)

1164
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Textbook Question

Complete the table of ¹H NMR data you'd generate for each of the following molecules.

(c)

960
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Textbook Question

For the hydrogen(s) screened in blue, draw the signal you would expect to see in a ¹H NMR spectrum. At which chemical shift would the signal appear?

(e)

952
views