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Question:

An organic compound 'X' having molecular formula C5H10O yields phenyl hydrazone and gives a negative response to the Iodoform test and Tollen's test. It produces n-pentane on reduction. 'X' could be: 3-pentanone, n-amyl alcohol, pentanal, 2-pentanone

n-amyl alcohol

3-pentanone

pentanal

2-pentanone

Solution:

An organic compound 'X' having molecular formula C5H10O yields phenyl hydrazone. This indicates the presence of a carbonyl group. It gives a negative response to the Iodoform test. This indicates the absence of a methyl keto group. Hence, n-amyl alcohol and 2-pentanone are ruled out. It gives a negative response to Tollen's test. This indicates the absence of an aldehyde group. Hence, pentanal is ruled out. It produces n-pentane on reduction. This indicates the presence of a 5-carbon backbone. 'X' could be 3-pentanone.