EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 9781319188962
Author: VOLLHARDT
Publisher: VST
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Chapter 3, Problem 27P

(a)

Interpretation Introduction

Interpretation: The isomeric products obtained after monobromination of propane should be drawn.

Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism.

Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(b)

Interpretation Introduction

Interpretation: The approximate ratio of products obtained, major product of monobromination and whether the selectivity exhibited by bromine is sufficient enough for formation of isomeric products in good yields should be drawn.

Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism.

Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

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When an unknown amine reacts with an unknown acid chloride, an amide with a molecular mass of 163 g/mol (M* = 163 m/z) is formed. In the infrared spectrum, important absorptions appear at 1661, 750 and 690 cm. The 13C NMR and DEPT spectra are provided. Draw the structure of the product as the resonance contributor lacking any formal charges. 13C NMR DEPT 90 200 160 120 80 40 0 200 160 120 80 40 0 DEPT 135 T 200 160 120 80 40 0 Draw the unknown amide. Select Dow Templates More Frage
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