Skip to main content
Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooksMullins 1st EditionCh. 15 - Structural Identification II: Nuclear Magnetic Resonance SpectroscopyProblem 64c
Chapter 14, Problem 64c

Draw the ¹H NMR spectrum you would expect to see for each of the molecules in Assessment 15.63.
(c) Hexagon shape representing a benzene ring, used in NMR spectrum analysis for organic molecules.

Verified step by step guidance
1
Identify the structure of the molecule in question from Assessment 15.63, part c. Determine the number of unique hydrogen environments in the molecule. Each unique environment will correspond to a different signal in the ¹H NMR spectrum.
Analyze the chemical environment of each set of equivalent hydrogens. Consider factors such as electronegativity of nearby atoms, hybridization of the carbon atoms to which the hydrogens are attached, and any resonance effects that might influence the chemical shift.
Predict the splitting pattern for each signal based on the number of neighboring hydrogens (n+1 rule). For example, if a set of hydrogens has two neighboring hydrogens, the signal will be split into a triplet.
Estimate the chemical shift range for each signal using typical ¹H NMR chemical shift values. For instance, hydrogens on sp³ hybridized carbons typically appear between 0-3 ppm, while those on sp² hybridized carbons appear between 4.5-7 ppm.
Consider the integration of each signal, which corresponds to the relative number of hydrogens contributing to that signal. This will help in determining the relative intensity of each peak in the spectrum.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?

Key Concepts

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

¹H NMR Spectroscopy

¹H NMR 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. Peaks in the spectrum correspond to different hydrogen environments, and their chemical shifts, multiplicity, and integration help deduce molecular structure.
Recommended video:
Guided course
10:06
General NMR Features

Chemical Shift

Chemical shift in NMR spectroscopy refers to the position of a signal in the spectrum, measured in parts per million (ppm). It indicates the electronic environment surrounding a nucleus, influenced by nearby electronegative atoms or functional groups. Understanding chemical shifts is crucial for identifying the types of hydrogen atoms present in a molecule and their relative positions.
Recommended video:
Guided course
11:44
1H NMR Chemical Shifts

Spin-Spin Coupling

Spin-spin coupling, or J-coupling, occurs when magnetic interactions between neighboring hydrogen nuclei split NMR signals into multiplets. This splitting provides information about the number of adjacent hydrogen atoms, helping to elucidate the connectivity and arrangement of atoms within a molecule. The pattern and number of peaks in a multiplet reveal the number of neighboring hydrogens.
Recommended video:
Guided course
02:54
Sonogashira Coupling Reaction
Related Practice
Textbook Question

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

(d)

1129
views
Textbook Question

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

(d)

1035
views
Textbook Question

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

(b)

1164
views
Textbook Question

For the molecules in Assessment 15.58, give an approximate chemical shift for each indicated carbon. [The range of correct answers is large here.].

(a)

1170
views
Textbook Question

For the molecules in Assessment 15.58, give an approximate chemical shift for each indicated carbon. [The range of correct answers is large here.].

(c)

1032
views
Textbook Question

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

(c)

960
views