Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 10, Problem 10PP
Interpretation Introduction

Interpretation:

On fractional distillation of a product mix, the fraction showing optical activity and the fraction that resolves into enantiomers are to be determined. Also, the characterstics of NMR indicating the identity of components in fraction are to be mentioned.

Concept introduction:

Radical reactions are those reactions that take place between free radicals in presence of light energy. In these reactions, changes in bonding occur with homolysis.

Higher alkanes react with halogens by free radical mechanism to form mono, di, tri and tetra-substituted alkyl halides.

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(i) Give reasons, with reference to compound structures, for each of the following observations: (i) (ii) The chemical shift value for a hydrogen attached to a benzene ring is greater than 6.0 ppm while that of a hydrogen attached to an alkyne is c. 2.5 ppm. IR spectroscopy alone can clearly distinguish between trimethylamine and (iii) H-NMR clearly distinguishes between propanethiol and propanol. propanamine.
The spectrum of compound F with molecular formula C5H602 is shown below. IR spectrum shows a medium intensity band at 3270, 2180 and 1690 cm-1. "H NMR: 8 (ppm) 1.3 (t, ЗH), 2.8 (s, 1H), 4.3 (q, 2н). (i) Give the degree of unsaturation of compound F. (ii) By using the IR and 'H NMR data given, deduce the structure of compound F.
10. For each of the following mixtures, suggest a separation technique and explain a basis for your choice: (a) Acetone (a volatile liquid) and benzaldehyde (b) N-Ethylpentanamine, butanamide and phenol. Explain.

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