Organic Chemistry&mod Mstg Etx Vp Ac Pkg
Organic Chemistry&mod Mstg Etx Vp Ac Pkg
1st Edition
ISBN: 9780134466729
Author: Bruice
Publisher: Pearson Education
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Chapter 19.7, Problem 16P
Interpretation Introduction

Interpretation:

The difference in the boiling point of imidazole and N-methylimidazole has to be explained.

Concept Introduction:

Imidazole is the aromatic compound and also the heterocyclic ring of histidine. It exists in both protonated and non-protonated form at pH=7.4. The lone pair on first nitrogen are a part of the pi cloud as they are present in p orbital whereas the lone pair electrons on third nitrogen are not a part of pi cloud because they are perpendicular to the p orbitals.

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Three amide isomers, N,N-dimethylformamide, N-methylacetamide, and propanamide, have respective boiling points of 153 °C (426 K), 202 °C (475 K), and 213 °C (486 K). Explain these boiling points in light of their structural formulas.
N-Methylpyrrolidine has a boiling point of 81 °C, and piperidine has a boiling point of 106 °C. Tetrahydropyran has a boiling point of 88 °C, and cyclopentanone has a boiling point of 141 °C. These two isomershave a boiling point difference of 53 °C. Explain why the two oxygen-containing isomers have a much larger boilingpoint difference than the two amine isomers
N-Methylpyrrolidine has a boiling point of 81 °C, and piperidine has a boiling point of 106 °C.  Explain the large difference (25 °C) in the boiling point for these two isomers.

Chapter 19 Solutions

Organic Chemistry&mod Mstg Etx Vp Ac Pkg

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