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2,3-Dimethyl-2-butene can be prepared by...

`2,3-`Dimethyl`-2-`butene can be prepared by heating which of the following compounds with a strong acid ?

A

`(CH_(3))_(2)C=CH-CH_(2)-CH_(2)`

B

`(CH_(3))_(2)CH-CH_(2)-CH=CH_(2)`

C

`(CH_(3))_(2)CH-underset(CH_(3))underset(|)(C)H-CH=CH_(2)`

D

`(CH_(3))_(2)C-CH=CH_(2)`

Text Solution

AI Generated Solution

The correct Answer is:
To determine which compound can be heated with a strong acid to prepare 2,3-dimethyl-2-butene, we need to analyze each given compound and see if it can lead to the desired product through carbocation rearrangement and elimination reactions. ### Step-by-Step Solution: 1. **Identify the Structure of the Desired Product:** - The structure of 2,3-dimethyl-2-butene is: ``` CH3 | CH3-C=CH-CH3 | CH3 ``` - This compound has a double bond between the second and third carbon atoms, with two methyl groups attached to the second carbon. 2. **Analyze Each Compound:** - **Option 1: CH3-C(CH3)=CH-CH2-CH3** - On heating with a strong acid, this compound would form a carbocation. However, the resulting alkene does not match the desired product. Therefore, this option is incorrect. - **Option 2: CH3-CH2-C(CH3)=O** - Upon heating with acid, this compound would also rearrange to form a different carbocation. The elimination process would not yield the desired product, so this option is also incorrect. - **Option 3: CH3-CH=CH-CH3** - This compound would form a secondary carbocation upon heating with acid. However, it would not lead to the formation of 2,3-dimethyl-2-butene, as it would yield a different alkene. Thus, this option is incorrect. - **Option 4: CH3-C(CH3)=CH2** - When this compound is heated with a strong acid, it forms a carbocation. The carbocation can undergo a methyl shift to form a more stable tertiary carbocation. The elimination of a proton from the appropriate carbon leads to the formation of 2,3-dimethyl-2-butene, which is the desired product. 3. **Conclusion:** - The correct compound that can be heated with a strong acid to yield 2,3-dimethyl-2-butene is **Option 4**.

To determine which compound can be heated with a strong acid to prepare 2,3-dimethyl-2-butene, we need to analyze each given compound and see if it can lead to the desired product through carbocation rearrangement and elimination reactions. ### Step-by-Step Solution: 1. **Identify the Structure of the Desired Product:** - The structure of 2,3-dimethyl-2-butene is: ``` CH3 ...
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