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Exercises · 9.5

Q.An alkene 'A' on ozonolysis gives a mixture of ethanal and pentan-3-one. Write structure and IUPAC name of 'A'.

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The alkene A is 3-ethylpent-2-ene (IUPAC name). Ozonolysis cleaves the double bond; ethanal (CH3CHO\text{CH}_3\text{CHO}) and pentan-3-one (CH3CH2COCH2CH3\text{CH}_3\text{CH}_2\text{COCH}_2\text{CH}_3) come from the two halves, so A must be CH3CH=C(CH2CH3)2\text{CH}_3\text{CH}=\text{C}(\text{CH}_2\text{CH}_3)_2.


The key idea here is retrosynthetic analysis of ozonolysis. Ozonolysis of an alkene breaks the carbon-carbon double bond and replaces it with two carbonyl groups (aldehydes or ketones). If you know the products, you can reconstruct the original alkene by joining the carbonyl carbons back together with a double bond.

Ethanal is CH3CHO\text{CH}_3\text{CHO} — that's a two-carbon aldehyde. Pentan-3-one is CH3CH2COCH2CH3\text{CH}_3\text{CH}_2\text{COCH}_2\text{CH}_3 — a five-carbon ketone with the carbonyl at position 3. So the alkene must have had a total of 2+5=72 + 5 = 7 carbons, and the double bond was between the carbon that became the aldehyde carbon and the carbon that became the ketone carbon.

Let's work through it step by step.

  1. Identify the fragments from the products.

    Ethanal: CH3−CHO\text{CH}_3-\text{CHO}. The carbonyl carbon (the CHO\text{CHO} carbon) was one end of the original double bond.

    Pentan-3-one: CH3CH2−CO−CH2CH3\text{CH}_3\text{CH}_2-\text{CO}-\text{CH}_2\text{CH}_3. The carbonyl carbon (the CO\text{CO} carbon) was the other end of the double bond.

  2. Reconnect the two carbonyl carbons with a double bond.

    Remove the oxygen from each carbonyl and join the two carbons. That gives:

CH3−CH=C(CH2CH3)2\text{CH}_3-\text{CH}=\text{C}(\text{CH}_2\text{CH}_3)_2

The left fragment (from ethanal) gives CH3CH=\text{CH}_3\text{CH}= — a two-carbon chain with the double bond at the end.

The right fragment (from pentan-3-one) gives =C(CH2CH3)2=\text{C}(\text{CH}_2\text{CH}_3)_2 — a central carbon attached to two ethyl groups.

  1. Determine the longest chain and number it. The alkene has 7 carbons total: 2 from the ethanal-derived end and 5 from the pentan-3-one-derived end (the central carbon plus two ethyl groups). The full structure is:

CH3−CH=C(CH2CH3)2\text{CH}_3-\text{CH}=\text{C}(\text{CH}_2\text{CH}_3)_2

To name it, find the longest chain that includes the double bond: starting from the left CH3\text{CH}_3, the chain runs through the double bond and continues into one of the two ethyl groups on the far carbon (the other ethyl group becomes a substituent). That gives a 5-carbon chain:

CH3C1−CHC2=CC3(CH2CH3)−CH2C4−CH3C5\underset{C1}{\text{CH}_3}-\underset{C2}{\text{CH}}=\underset{C3}{\text{C}}(\text{CH}_2\text{CH}_3)-\underset{C4}{\text{CH}_2}-\underset{C5}{\text{CH}_3} …

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