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Use your brain power · Q16

Q.On ozonolysis an alkene forms the following carbonyl compounds. Draw the structure of unknown alkene from which these compounds are formed. HCHO and CH3COCH2CH3

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Step 1. Read each carbonyl fragment back to its parent alkene carbon. As section 15.2.4 explains, ozonolysis puts a C=O exactly where the C=C used to be, so each product's carbonyl carbon corresponds to one of the two original double-bond carbons, and the OTHER groups on that carbonyl carbon are exactly the groups that were already attached to that alkene carbon.

Step 2. Interpret HCHO. Formaldehyde, H2C=O, has only two hydrogens on its carbonyl carbon -- so the corresponding alkene carbon must have been a terminal =CH2 (two hydrogens, no carbon substituents).

Step 3. Interpret CH3COCH2CH3. Butan-2-one, CH3-CO-CH2-CH3, has a methyl group and an ethyl group on its carbonyl carbon -- so the corresponding alkene carbon must have carried both a CH3 and a CH2CH3 substituent.

Step 4. Reassemble the alkene. Joining the two carbons back together at their former double bond: CH2=C(CH3)(CH2CH3), which is 2-methylbut-1-ene.

Step 5. Sanity-check the formula. 2-Methylbut-1-ene is C5H10; splitting it at the double bond into (CH2=) and (=C(CH3)(CH2CH3)) exactly regenerates HCHO and CH3COCH2CH3 on ozonolysis, confirming the structure.

✓Final answer

The unknown alkene is 2-methylbut-1-ene: CH2=C(CH3)-CH2-CH3.

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