Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter SRP, Problem 29P
Interpretation Introduction

Interpretation:

The structure is to be proposed for the compound Z with the molecular formula C8H16 with given information.

Concept introduction:

舧 Nuclear Magnetic Resonance (NMR) is one of the most capable analytical techniques used for determining the functional groups and how the atoms are structured and arranged in a molecule.

舧 Few elements, such as 13C and 1H >, have nuclei behaving as magnets about an axis. These elements are placed in magnetic field irradiated with electromagnetic energy of specific frequency and the nuclei tend to absorb energy via magnetic resonance. There is this graph that shows energy absorption frequencies and intensities of a sample kept in the magnetic field called nuclear magnetic resonance (NMR).

舧 In NMR spectroscopy, the proton nuclear magnetic resonance (1HNMR) is used to find out the structure of molecules with the help of 1H atom within the molecules.

舧 Induced magnetic field consists of electricity generated from movement in a magnetic field.

13C NMR is only used in the observation of isotopes of carbon atoms.

舧 In NMR spectroscopy, the proton nuclear magnetic resonance (1HNMR) is used in order to find out the structure of molecules with the help of 1H atom within the molecules.

舧 The splitting of the molecules is determined by the (n+1) peaks in the NMR resonance in which n is the number of hydrogens on the adjacent atom.

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Treatment of ketone A with ethynyllithium (HC≡CLi) followed by D3O+ afforded a compound B of molecular formula C12H13DO3, which gave an IR absorption at approximately 1715 cm−1. What is the structure of B and how is it formed?
Reaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed by treatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 18.
Identify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?

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Organic Chemistry

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