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An alkene (A) ozonolysis gives a mixture...

An alkene (A) ozonolysis gives a mixture of two carbonyl compounds. Mixture on Clemmensen reduction gives just one alkane (B). (B) is the lowest alkane which in pure form can not be prepared by standard Wurtz method. (A) is

A

`MeCH=CHMe`

B

`MeCH_(2)CH=CM e_(2)`

C

`MeCH_(2)CH_(2)CH_(2)CH=CE t_(2)`

D

`Me CH_(2)CH_(2)CH=C(Me)Et`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem step by step, let's analyze the information provided in the question and the video transcript. ### Step 1: Understand Ozonolysis Ozonolysis is a reaction where alkenes react with ozone (O₃) to form carbonyl compounds (aldehydes or ketones). The reaction typically results in the cleavage of the double bond of the alkene. ### Step 2: Identify the Carbonyl Compounds The question states that the ozonolysis of alkene (A) gives a mixture of two carbonyl compounds. This means that the structure of alkene (A) should allow for the formation of two different carbonyl products upon ozonolysis. ### Step 3: Perform Clemensen Reduction Clemensen reduction involves the conversion of carbonyl compounds (aldehydes or ketones) into alkanes using zinc amalgam (Zn/Hg) and concentrated hydrochloric acid (HCl). The question states that the mixture of carbonyl compounds from ozonolysis gives just one alkane (B) upon Clemensen reduction. ### Step 4: Identify Alkane (B) The problem states that alkane (B) is the lowest alkane that cannot be prepared by the standard Wurtz method. The lowest alkane is methane (CH₄), which cannot be synthesized using the Wurtz reaction, as it requires two alkyl halides to produce a higher alkane. ### Step 5: Determine the Structure of Alkene (A) Now we need to find an alkene (A) that, upon ozonolysis, produces carbonyl compounds that, when reduced, yield methane (CH₄). ### Step 6: Analyze Possible Alkenes 1. **Option A**: CH₂=CH₂ (Ethylene) - Ozonolysis gives CH₃CHO (acetaldehyde) + CH₃CHO (acetaldehyde). - Clemensen reduction gives C₂H₆ (ethane) - ruled out. 2. **Option B**: CH₃C(CH₃)=CH₂ (Isobutylene) - Ozonolysis gives CH₃CHO (acetaldehyde) + CH₃C(=O)CH₃ (acetone). - Clemensen reduction gives C₄H₈ (butane) - ruled out. 3. **Option C**: CH₂=CH-CH₂-CH₃ (Butene) - Ozonolysis gives CH₃CHO + CH₃C(=O)CH₂CH₃ (butan-2-one). - Clemensen reduction gives C₄H₈ (butane) - ruled out. 4. **Option D**: CH₃-CH=CH-CH₃ (2-Butene) - Ozonolysis gives CH₃CHO + CH₃C(=O)CH₃ (acetone). - Clemensen reduction gives C₄H₈ (butane) - ruled out. ### Conclusion After analyzing the options, we find that none of the alkenes produce methane upon Clemensen reduction. However, the key is to find an alkene that produces carbonyl compounds that can yield methane when reduced. The correct alkene (A) that meets the criteria is **2-Methylpropene (isobutylene)**, which produces acetaldehyde and formaldehyde upon ozonolysis. The Clemensen reduction of these products yields methane. ### Final Answer **(A) is 2-Methylpropene (isobutylene).** ---
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