The product obtained from the Wittig reaction has to be identified. Concept introduction: Alkyl bromide reacts with triphenylphosphine to form triphenylphosphonium salt. The salt is further treated with base to from phosphonium ylide. Phosphonium ylide reacts with aldehyde or ketone and undergoes [ 2 + 2 ] cycloaddition mechanism to form alkene as the major product. Triphenylphosphine oxide is eliminated in the reaction. This reaction is known as Wittig reaction. The 1 H NMR is used to predict the structure of the organic compounds. The resonant frequency of a nucleus with respect to a relative compound is called the chemical shift. Chemical shift is used to identify the nature of the proton. Spin-spin coupling causes the splitting of signal for each type of nucleus. The proton splits the neighbouring proton by the ( n + 1 ) rule. The integer, n represesnts the number of protons. Number of signals gives the chemical environment of the proton. If protons are chemically equivalent, then one signal is produce in the NMR spectra.

Question

Shown below is the 1H NMR spectrum of the alkyl bromide used to make the phosphonium ylide that reacts with a ketone in a Wittig reaction to form acompound with molecular formula C11H14. What product is obtained from the Wittig reaction?

Answer 1

Question

Chapter 16, Problem 87P

Interpretation Introduction

Interpretation:

The product obtained from the Wittig reaction has to be identified.

Concept introduction:

Alkyl bromide reacts with triphenylphosphine to form triphenylphosphonium salt. The salt is further treated with base to from phosphonium ylide. Phosphonium ylide reacts with aldehyde or ketone and undergoes [2+2] cycloaddition mechanism to form alkene as the major product. Triphenylphosphine oxide is eliminated in the reaction. This reaction is known as Wittig reaction.

The 1H NMR is used to predict the structure of the organic compounds. The resonant frequency of a nucleus with respect to a relative compound is called the chemical shift. Chemical shift is used to identify the nature of the proton. Spin-spin coupling causes the splitting of signal for each type of nucleus. The proton splits the neighbouring proton by the (n+1) rule. The integer, n represesnts the number of protons. Number of signals gives the chemical environment of the proton. If protons are chemically equivalent, then one signal is produce in the NMR spectra.

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