Organic Chemistry Study Guide and Solutions
Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 19, Problem 19.9P
Interpretation Introduction

Interpretation:

The compound between vanillin and isovanillin that would have a ππ UV absorption at the greater λmax when the compound is dissolved in NaOH the solution is to be identified. The explanation for the corresponding answer is to be stated.

Concept introduction:

Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Molecules have bonding or non-bonding electrons that can absorb light while promoting electrons from the ground state (HOMO) to an excited state (LUMO). The light absorbed is usually in the UV or visible region. Conjugation in the molecule also affects the wavelength of light absorbed.

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An unknown compound A (molecular formula C7H14O) was treated withNaBH4 in CH3OH to form compound B (molecular formula C7H16O).Compound A has a strong absorption in its IR spectrum at 1716 cm−1.Compound B has a strong absorption in its IR spectrum at 3600−3200cm−1. The 1H NMR spectra of A and B are given. What are the structuresof A and B?
As we will learn in Chapter 17, reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600−3200, 3303, 2938, and 2120 cm−1. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?

Chapter 19 Solutions

Organic Chemistry Study Guide and Solutions

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NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY