A sweet smelling organic compound A (mol. formula C, H 1602 ) on reaction with lithium aluminium… 1 answer below »

A sweet smelling organic compound A (mol. formula C, H 1602 ) on reaction with lithium aluminium hydride

furnishes a single primary alcohol B. Whereas reaction ofA with an excess of methylmagnesium bromide

furnishes two alcohols B and C. In the NMR spectrum, compound B exhibits signals at 6 3.8 (2H, d, J = 7

Hz), 1.8(1 H, m). 1.6( 1 H, brs, exchangeable with D20 ) and 0.9 (6 H, d, J = 7.2 Hz). Identify the structures

of the compounds A, B and C, and explain the reactions.

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