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An alcohol, on dehydration produces an a...

An alcohol, on dehydration produces an alkene which on ozonolysis yields two molecules of ethanal. The alcohol is, therefore.

A

`CH_(3)CH_(2)CH_(2)OH`

B

`CH_(3)CH_(2)OH`

C

`CH_(3)-underset(CH_(3))underset(|)(C)H-CH_(2)OH`

D

`CH_(3)CH_(2)-underset(OH)underset(|)(C)H-CH_(3)`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem step by step, we need to identify the alcohol that, upon dehydration, produces an alkene which then undergoes ozonolysis to yield two molecules of ethanal (acetaldehyde). ### Step 1: Understand the Products We know that ozonolysis of the alkene yields two molecules of ethanal (CH₃CHO). This means that the alkene must be structured in such a way that when it is cleaved by ozone, it produces two molecules of ethanal. ### Step 2: Identify the Structure of Ethanal Ethanal (acetaldehyde) has the formula CH₃CHO. Therefore, we need to consider how two molecules of this compound can be formed from an alkene. ### Step 3: Determine the Alkene Structure To produce two ethanal molecules from an alkene, the alkene must be butene (C₄H₈). The ozonolysis of butene can yield two ethanal molecules. ### Step 4: Identify the Alcohol Now, we need to find an alcohol that can dehydrate to form butene. The most straightforward candidate is 2-butanol (C₄H₁₀O), which is a secondary alcohol. ### Step 5: Dehydration Reaction When 2-butanol undergoes dehydration (removal of water), it forms butene (specifically, 2-butene). The reaction can be represented as follows: \[ \text{C}_4\text{H}_{10}\text{O} \xrightarrow{\text{H}^+} \text{C}_4\text{H}_8 + \text{H}_2\text{O} \] ### Step 6: Ozonolysis of Butene The ozonolysis of 2-butene will yield two molecules of ethanal: \[ \text{C}_4\text{H}_8 + \text{O}_3 \rightarrow 2 \text{C}_2\text{H}_4\text{O} \] ### Conclusion Thus, the alcohol that upon dehydration produces an alkene which on ozonolysis yields two molecules of ethanal is **2-butanol**. ### Final Answer The alcohol is **2-butanol**. ---
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