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