Chapter 18, Problem 18.100P

Interpretation Introduction

Interpretation:

By using the given NMR spectrum, the structure of the product and mechanism of the reaction are to be determined.

Concept introduction:

For the analysis of the molecular formula of organic molecules, the sites of unsaturation, also known as IHD, are used for the determination of total number of ring and $\text{π}$ bonds in the structure.

Alkene hydrogen indicates the chemical shift at $\text{2}\text{.1 - 2}\text{.2 δ}$, and ${\text{CH}}_{\text{3}}$ groups, which are slightly deshielded, indicate the chemical shift at $\text{5}\text{.8 - 5}\text{.9 δ}$ respectively.

In case of proton transfer reaction, proton is abstracted by the electronegative atom like oxygen.

In nucleophilic addition reaction, the nucleophile will attack the most electropositive carbon which results in the formation of a new bond.

Heterolysis is the removal of water.

In E1 elimination reaction, deprotonation of a hydrogen nearby the carbocation results in the formation of an alkene.