ORG CHEM W/ EBOOK & SW5 + STUDY GUIDE
ORG CHEM W/ EBOOK & SW5 + STUDY GUIDE
2nd Edition
ISBN: 9780393666144
Author: KARTY
Publisher: NORTON
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Chapter 14, Problem 14.55P
Interpretation Introduction

Interpretation:

The difference in the calculated dipole moments of the two compounds J and K is to be explained.

Concept introduction:

In an unsaturated ring with an incomplete conjugation or a saturated ring with a suitable number of double-bonded substituents, it is possible for the ring to gain aromatic stabilization through a change in hybridization and/or through resonance. In this case, the extra stability gain drives such transformations, and the ring behaves like an aromatic compound.

If this process involves a charge separation, the molecule may gain polarity even if it is not inherently polar.

Dipole moment is the product of the charge and the distance separating the opposite charges. Generally, the charges in such structures are just unit charges, so the dipole moment primarily depends on their separation. Larger the distance between the centers of the positive and negative charge, larger the dipole moment.

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2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity
Interpreting NMR spectra is a skill that often requires some amount of practice, which, in turn, necessitates access to a collection of NMR spectra. Beyond Labz Organic Synthesis and Organic Qualitative Analysis have spectral libraries containing over 700 1H NMR spectra. In this assignment, you will take advantage of this by first predicting the NMR spectra for two closely related compounds and then checking your predictions by looking up the actual spectra in the spectra library. After completing this assignment, you may wish to select other compounds for additional practice. 1. Write the IUPAC names for the following two structures: Question 2 Question 3 2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled**
11:14 ... worksheets.beyondlabz.com 3. To check your predictions, click this link for Interpreting NMR Spectra 1. You will see a list of all the - compounds in the spectra library in alphabetical order by IUPAC name. Hovering over a name in the list will show the structure on the chalkboard. The four buttons on the top of the Spectra tab in the tray are used to select the different spectroscopic techniques for the selected compound. Make sure the NMR button has been selected. 4. Scroll through the list of names to find the names for the two compounds you have been given and click on the name to display the NMR spectrum for each. In the NMR tables below, list the chemical shift, the splitting, and the number of hydrogens associated with each peak for each compound. Compare your answers to your predictions. **Not all slots must be filled** Peak Chemical Shift (d) Multiplicity 1 2 3 4 5

Chapter 14 Solutions

ORG CHEM W/ EBOOK & SW5 + STUDY GUIDE

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