Macroscale and Microscale Organic Experiments
Macroscale and Microscale Organic Experiments
7th Edition
ISBN: 9781305577190
Author: Kenneth L. Williamson, Katherine M. Masters
Publisher: Brooks Cole
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Chapter 19, Problem 4Q
Interpretation Introduction

Interpretation: The close resemblance of 1H and 13C spectrum of cyclohexene needs to be explained. The 13C spectrum of cyclohexene and cyclohexanol needs to be compared.

Concept Introduction:

Both 1H spectrum and 13C spectrum comes under NMR (nuclear magnetic resonance) spectroscopy. The NMR interpretation has an important role in the identification of molecules. For any unknown compound, its NMR spectra can help in interpreting its structure. NMR spectrum contains splitting pattern, integral areas and coupling constant.

In 1H spectrum and 13C spectrum, chemical shift is basically the Larmor frequency of a nuclear spin to its chemical environment. Generally, tetramethyl silane (TMS) is used as standard to calculate the chemical shift if compounds as the chemical shift for TMS is 0 ppm. In NMR spectrum, protons having same chemical shift due to symmetry within the molecule have chemical equivalence.

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The oxidation of 3-pentanol to 3-pentanone was performed in the lab and an IR was taken of the finished product.  (a) what are the key functional groups in the starting material, 3-pentaol? (b) what are the key functional groups in the product, 3-pentanone? (c) based on the IR spectrum below, was the experiment successful, and, if so, how pure was the product? Explain your reasoning.
Identify the C-H out-of-plane bending vibrations in the infrared spectrum of 4- methylcyclohexene. What structural information can be obtained from these bands?

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Macroscale and Microscale Organic Experiments

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