GATE CY 2023 Question Paper (05-Feb-2023) (Shift 2)

A compound, C₁₅H₁₆O₂, has the following spectral data;

¹H NMR (ppm): 9.16 (s), 6.89 (d, 𝐽 = 8 Hz), 6.64 (d, 𝐽 = 8 Hz), 1.53 (s)

¹³C NMR (ppm): 154.7, 140.9, 127.1, 114.4, 40.7, 30.7

The structure of the compound is

The major product formed in the given reaction sequence is

E and F in the given reaction scheme are

M and N in the given reaction scheme are

In the ¹H NMR spectrum, multiplicity of the signal (bold and underlined H atom) in the following species is

(I) [HNi(OPEt₃)₄]⁺

(II) Ph₂Si(Me)H

(III) PH₃

(IV) (Cp)₂ZrH₂ (Cp = pentamethylcyclopentadienyl)