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Ch. 14 - NMR Spectroscopy
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
All textbooksBruice 8th EditionCh. 14 - NMR SpectroscopyProblem 14c
Chapter 15, Problem 14c

Without referring to Table 14.1, label the proton or set of protons in each compound that gives the signal at the lowest frequency a, at the next lowest b, and so on.
c. ClCH2CH2CH2Cl

Verified step by step guidance
1
Step 1: Analyze the structure of the molecule provided. The molecule contains three carbon atoms, each bonded to hydrogen atoms and bromine atoms. The bromine atoms are electronegative and will influence the chemical shift of nearby protons in NMR spectroscopy.
Step 2: Identify the protons in the molecule. There are three sets of protons: (1) the protons on the CH2 group directly bonded to the bromine atom on the left, (2) the protons on the middle CH2 group, and (3) the protons on the CH2 group bonded to the bromine atom on the right.
Step 3: Consider the electronegativity of bromine and its effect on the chemical shift. Bromine is highly electronegative and deshields nearby protons, causing them to resonate at higher frequencies in NMR spectroscopy. Protons farther from bromine will experience less deshielding and resonate at lower frequencies.
Step 4: Rank the protons based on their proximity to bromine atoms. The protons on the CH2 group directly bonded to bromine will resonate at the highest frequency due to the strong deshielding effect. The protons on the middle CH2 group, which are equidistant from both bromine atoms, will resonate at a lower frequency. The protons on the CH2 group bonded to the bromine atom on the right will resonate at the next highest frequency.
Step 5: Assign labels to the protons based on their chemical shift. The protons on the middle CH2 group will give the signal at the lowest frequency and are labeled 'a'. The protons on the CH2 group bonded to the bromine atom on the left will give the signal at the next lowest frequency and are labeled 'b'. The protons on the CH2 group bonded to the bromine atom on the right will give the signal at the highest frequency and are labeled 'c'.

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Key Concepts

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

Chemical Shift in NMR Spectroscopy

In nuclear magnetic resonance (NMR) spectroscopy, the chemical shift refers to the resonance frequency of a nucleus relative to a standard in a magnetic field. It is influenced by the electronic environment surrounding the nucleus, with protons in electron-rich environments appearing at higher frequencies (downfield) and those in electron-poor environments appearing at lower frequencies (upfield). Understanding chemical shifts is crucial for interpreting NMR spectra and identifying different types of protons in a compound.
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Electronegativity and Inductive Effect

Electronegativity is the tendency of an atom to attract electrons towards itself. In organic compounds, electronegative atoms like bromine can exert an inductive effect, pulling electron density away from nearby protons. This effect can deshield the protons, causing them to resonate at lower frequencies in NMR spectroscopy. Recognizing the influence of electronegative substituents is essential for predicting the order of proton signals in an NMR spectrum.
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Proton Environment and Signal Splitting

The environment of protons in a molecule affects their NMR signals. Protons that are in similar environments will resonate at the same frequency, while those in different environments will produce distinct signals. Additionally, the splitting of signals due to neighboring protons (n+1 rule) provides information about the number of adjacent protons. Understanding these concepts helps in accurately labeling and interpreting the signals in an NMR spectrum.
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Related Practice
Textbook Question

[18]-Annulene shows two signals in its 1H NMR spectrum: one at 9.25 ppm and the other to the right of the TMS signal at –2.88 ppm. What hydrogens are responsible for each of the signals? (Hint: Look at the direction of the induced magnetic field outside and inside the benzene ring in Figure 14.6.)

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Textbook Question

Which underlined proton (or sets of protons) has the greater chemical shift (that is, the higher frequency signal)?

c.

d.

1
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Textbook Question

Without referring to Table 14.1, label the proton or set of protons in each compound that gives the signal at the lowest frequency a, at the next lowest b, and so on.

h.

1
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Textbook Question

Which underlined proton (or sets of protons) has the greater chemical shift (that is, the higher frequency signal)?

a.

b.

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Textbook Question

Without referring to Table 14.1, label the proton or set of protons in each compound that gives the signal at the lowest frequency a, at the next lowest b, and so on.

e.

3
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Textbook Question

If two signals differ by 90 Hz in a 300 MHz spectrometer, by how much do they differ in a 500 MHz spectrometer