1 mole of a symmetrical alkene on ozonolysis gives 2 moles of an aldehyde with molecular mass 44w. The alkene is
Answer & explanation
Correct answer: option 4
The correct answer is Option (4) → But-2-ene.
Let us go through the ozonolysis of a symmetrical alkene step by step, understanding how it produces two moles of aldehyde with a molecular mass of 44 g/mol, and why the correct alkene is but-2-ene.
Ozonolysis is a reaction where an alkene reacts with ozone \((O_3)\) to cleave the double bond between carbon atoms.
After ozonolysis, a reductive workup (typically with zinc and water or dimethyl sulfide) converts the cleaved bond into carbonyl groups (either aldehydes or ketones).
Aldehyde with Molar Mass 44 g/mol
The reaction produces two moles of aldehyde from one mole of the alkene.
The molecular mass of the aldehyde is 44 g/mol.
We can deduce that this aldehyde is acetaldehyde (ethanal, \(CH_3CHO\)). The molar mass of acetaldehyde is:
\(\text{Molecular mass of }CH_3CHO = 12 (C) + 3 (H) + 12 (C) + 1 (H) + 16 (O) = 44 \, \text{g/mol}\)
Identifying the Symmetrical Alkene
The alkene must be symmetrical, meaning that it is structured in such a way that when the double bond breaks, it produces two identical aldehyde molecules.
Based on the reaction information, the alkene forms two moles of acetaldehyde \((CH_3CHO)\), a 2-carbon aldehyde.
Step-by-Step Analysis of Each Option
(1) Ethene \((C_2H_4)\):
Ethene is the simplest alkene: \(CH_2=CH_2\)
Ozonolysis of ethene would give:
\(CH_2=CH_2 + O_3 \longrightarrow 2 \, \text{formaldehyde} \, (\text{HCHO})\)
Formaldehyde has a molecular mass of 30 g/mol, not 44 g/mol.
Therefore, ethene is not the correct answer.
(2) Propene \((C_3H_6)\):
Propene is a 3-carbon alkene: \(CH_3-CH=CH_2\)
Ozonolysis of propene would give acetaldehyde \((CH_3CHO)\) and formaldehyde \((HCHO)\)
\(CH_3-CH=CH_2 + O_3 \longrightarrow CH_3CHO + HCHO\)
While acetaldehyde has the desired molecular mass of 44 g/mol, ozonolysis of propene gives one mole of acetaldehyde and one mole of formaldehyde. This does not match the information that two moles of aldehyde with a mass of 44 g/mol are produced.
Thus, propene is not the correct answer.
(3) But-1-ene:
But-1-ene is a 4-carbon alkene with the double bond at the end:
\(CH_2=CH-CH_2-CH_3\)
Ozonolysis of but-1-ene would produce acetaldehyde \((CH_3CHO)\) and propanal \((CH_3CH_2CHO)\):
\(CH_2=CH-CH_2-CH_3 + O_3 \longrightarrow CH_3CHO + CH_3CH_2CHO\)
Propanal has a molecular mass of 58 g/mol, while acetaldehyde has a mass of 44 g/mol. Since two different aldehydes are produced, this does not match the requirement of two moles of aldehyde with a mass of 44 g/mol.
Thus, but-1-ene is not the correct answer.
(4) But-2-ene:
But-2-ene is a symmetrical alkene with the double bond in the middle: \(CH_3-CH=CH-CH_3\)
Ozonolysis of but-2-ene would cleave the double bond symmetrically and produce two moles of acetaldehyde \((CH_3CHO)\):
\(CH_3-CH=CH-CH_3 + O_3 \longrightarrow 2 \, CH_3CHO\)
Both molecules produced are acetaldehyde with a molecular mass of 44 g/mol.
This matches the condition of producing two moles of an aldehyde with a molecular mass of 44 g/mol.
Conclusion
The correct alkene is But-2-ene because ozonolysis of but-2-ene gives 2 moles of acetaldehyde \(CH_3CHO)\), each with a molecular mass of 44 g/mol.
Therefore, the answer is But-2-ene.