Question 17 of 32intermediate🔧 ApplyShort Answer2 marks

Propanal and pentan-3-one are the ozonolysis products of an alkene? What is the structural formula of the alkene?

Correct Answer

The structural formula of the alkene is CH3CH2CH=C(CH2CH3)2\text{CH}_3\text{CH}_2\text{CH}=\text{C}(\text{CH}_2\text{CH}_3)_2.

Exercise: EXERCISES | Q: 9.7 | (Page Page 33)
For More Understanding

Explanation

Ozonolysis of an alkene cleaves the carbon-carbon double bond, converting the double-bonded carbons into carbonyl carbons. To find the original alkene, we remove the oxygen atoms from the carbonyl groups of the ozonolysis products (propanal and pentan-3-one) and join the two fragments with a double bond. Propanal (CH3CH2CHO\text{CH}_3\text{CH}_2\text{CHO}) provides the CH3CH2CH=\text{CH}_3\text{CH}_2\text{CH}= fragment, and pentan-3-one (CH3CH2COCH2CH3\text{CH}_3\text{CH}_2\text{COCH}_2\text{CH}_3) provides the =C(CH2CH3)2=\text{C}(\text{CH}_2\text{CH}_3)_2 fragment. Joining these gives the alkene CH3CH2CH=C(CH2CH3)2\text{CH}_3\text{CH}_2\text{CH}=\text{C}(\text{CH}_2\text{CH}_3)_2.

Solution Steps

  1. Step 1: Identify the ozonolysis products: propanal (CH3CH2CHO\text{CH}_3\text{CH}_2\text{CHO}) and pentan-3-one (CH3CH2COCH2CH3\text{CH}_3\text{CH}_2\text{COCH}_2\text{CH}_3).

  2. Step 2: Remove the oxygen atoms from the carbonyl groups of both products to get the alkene fragments: CH3CH2CH=\text{CH}_3\text{CH}_2\text{CH}= and =C(CH2CH3)2=\text{C}(\text{CH}_2\text{CH}_3)_2.

  3. Step 3: Join the two fragments at the double bond to obtain the structural formula of the alkene: CH3CH2CH=C(CH2CH3)2\text{CH}_3\text{CH}_2\text{CH}=\text{C}(\text{CH}_2\text{CH}_3)_2.