GATE CY 2016 Question Paper (31-Jan-2016) (Shift 2)

On reacting 1.55 g of a diol with an excess of methylmagnesium iodide, 1.12 L (corrected to STP) of methane gas is liberated. The molecular mass (g mol${}^{-1}$) of the diol is ________

The structure of the compound having the following characteristic spectral data, is IR: $1690{\text{ cm}}^{-1}$;

${}^{1}H$ -NMR: 1.30 (3H, t, J = 7.2 Hz); 2.41 (2H, q, J = 7.2 Hz); 2.32 (3H, s); 7.44 (1H, t, J = 7.0 Hz); 7.57 (1H, dt, J = 7.0, 3.0 Hz); 7.77 (1H, t, J = 3.0 Hz); 7.90 (1H, dt, J = 7.0, 3.0 Hz);

EI Mass: m/z 119 (100%); 57 (80%).

The major products X and Y formed in the following synthetic scheme, are

The major products S and T formed in the following synthetic scheme, are

Among the following, the transformation(s) that can be accomplished using umpolung concept is(are)