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Tests for carbonyl compounds
Appears in
Concepts tested here
- Iodoform test 2
- Identifying a ketone from tests
All Questions
2015 AIPMT-I 1 question
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An organic compound 'X' having molecular formula $C_5H_{10}O$ yields phenyl hydrazone and gives negative response to the Iodoform test and Tollens' test. It produces n-pentane on reduction. 'X' could be:Forms a phenylhydrazone, so X is a carbonyl compound.
Negative Tollens' test, so it is a ketone, not an aldehyde.
Negative iodoform test, so it has no $CH_3CO-$ group.
Reduction gives n-pentane, so the chain is unbranched: X is 3-pentanone, $CH_3CH_2COCH_2CH_3$.
$CH_3CH_2COCH_2CH_3 \xrightarrow{Zn-Hg/HCl} CH_3CH_2CH_2CH_2CH_3$
2012 AIPMT-MAINS 1 question
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Which of the following compounds will give a yellow precipitate with iodine and alkali?A yellow precipitate of iodoform ($CHI_3$) is given by compounds having the $CH_3-CO-$ group attached to C or H.
Acetophenone has this group: $C_6H_5COCH_3 \xrightarrow{I_2/NaOH} C_6H_5COONa + CHI_3\downarrow$
In methyl acetate and acetamide the $CH_3CO-$ group is attached to O or N, so they do not give the test.
As per the key the answer is acetophenone.
2012 AIPMT-PRE 1 question
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$CH_3CHO$ and $C_6H_5CH_2CHO$ can be distinguished chemically byBoth compounds are aldehydes, so both respond to Fehling's, Benedict's and Tollens' tests. These tests cannot tell them apart.
The iodoform test is given only by aldehydes and ketones that have the $CH_3-CO-$ group.
$CH_3CHO$ has this group: $CH_3CHO + 3I_2 + 4NaOH \rightarrow CHI_3 + HCOONa + 3NaI + 3H_2O$, giving a yellow precipitate of iodoform.
$C_6H_5CH_2CHO$ has no $CH_3-CO-$ group, so it gives no precipitate.
So the two are distinguished by the iodoform test.
