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Q.

0.40 g of an organic compound (A), (M.F.- C5H8O) reacts with x mole of CH3MgBr to liberate 224 mL of a gas at STP. With excess of H2, (A) gives pentan-1-ol. The correct structure of (A) is :

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a

HCCCH2CH2CH2OH

b

CH3CH2CCCH2OH

c

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d

CH3CCCH2CH2OH

answer is C.

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Detailed Solution

mol. mass of A = 12x5+ 8 + 16 = 84g
moles of A=0.40g84g = 0.005moles
moles of gas released at STP = 224 mL22.4 L = 0.01 moles
0.005 moles of A release 0.01 moles of gas. 
i. e., ratio of 1 : 2.
Hence there must be two acidic H in the compound A. One acidic H is from alcohol the other must be terminal alkyne as only the H attached to terminal alkynes are acidic.

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Hence option (d) is incorrect.

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