Q69. - Organic Chemistry

Question

Question: Treatment of W with CH₃Li, followed by CH₃l, affords compound Y (C₇H₁₄O ) as the major product. Y shows a strong absorption in its IR spectrum at  , and its 1 H NMR spectrum is given below. (a) Propose a structure for Y. (b) Draw a stepwise mechanism for the conversion of W to Y.

Step-by-Step Solution

Answer

Answer

a.

b.

Step 1: NMR spectroscopy

The singlet, doublet, triplet signal, and so on of a proton depend upon the protons connected to the adjacent atom.

Step 2: Steps involved in the reaction

(a)

 

The reaction is shown below:

                       Structure of Y

 

 

The NMR spectra of Y is explained as follows:

                       Structure of Y 

(b)

 

The mechanism is shown below:

                                   Conversion of W to Y