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Question

An organic compound A with molecular formula C5H12O undergoes iodoform reaction, reacts with PCC to form compound B. Compound A when reacts with Na metal evolves bubbles of H2 gas. Identify the structure of compound B and write all chemical reactions involved.

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Solution

Dear Student,

Compound A reacts with PCC and reacts with Na metal to evolve H2 gas, therefore it should be an alcohol. Also, it shows iodoform reaction and this indicates the presence of -C(OH)CH3 group. Therefore, compound A is CH3CH2CH2CH(OH)CH3CH3CH2CH2CH(OH)CH3 + I2 +NaOH CHI3 +CH3CH2CH2COO- + H2OCH3CH2CH2CH(OH)CH3 + Na CH3CH2CH2CH(O-Na+)CH3 + H2Now, PCCoxidises secondary alcohols to ketones, thereforeCH3CH2CH2CH(OH)CH3 PCC CH3CH2CH2COCH3 (B)

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