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(CH3)2 CH CH (CH3) OHoverset(Acid)unders...

`(CH_3)_2 CH CH (CH_3) OHoverset(Acid)underset(-H_2O)rarr X`
The major product obtained in this reaction is

A

`(CH_3)_2 CHCH=CH_2`

B

`(CH_3)_2C=CH-CH_3`

C

1:1 mixture of (1) and (2)

D

None of the above

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem of determining the major product obtained from the dehydration of (CH₃)₂CHCH(CH₃)OH in the presence of acid, we can follow these steps: ### Step 1: Identify the Reactant The reactant is (CH₃)₂CHCH(CH₃)OH, which is 2-methyl-2-butanol. This alcohol will undergo dehydration in the presence of an acid. **Hint:** Look for the structure of the alcohol and identify the functional groups. ### Step 2: Protonation of the Alcohol In the presence of acid (H⁺), the hydroxyl (-OH) group of the alcohol gets protonated, forming a better leaving group (water). The oxygen of the -OH group uses its lone pair to bond with the proton (H⁺), resulting in a positively charged oxonium ion. **Hint:** Remember that protonation increases the leaving ability of the -OH group. ### Step 3: Formation of Carbocation Once the water molecule leaves, a carbocation is formed. In this case, the carbocation formed is a secondary carbocation because the positively charged carbon is attached to two other carbon atoms. **Hint:** Identify the type of carbocation formed (primary, secondary, tertiary) as it influences stability. ### Step 4: Carbocation Rearrangement The secondary carbocation can undergo rearrangement to form a more stable tertiary carbocation through a 1,2-hydride shift. A hydrogen atom from an adjacent carbon shifts to the carbocation, stabilizing it. **Hint:** Look for possible rearrangements that can lead to a more stable carbocation. ### Step 5: Elimination to Form Alkene After the formation of the more stable carbocation, a proton (H⁺) is removed from an adjacent carbon atom, leading to the formation of a double bond. This results in the formation of an alkene. **Hint:** Identify the location of the double bond and ensure it follows Zaitsev's rule, which states that the more substituted alkene is favored. ### Step 6: Determine the Major Product The major product will be the more substituted alkene, which is formed by the elimination of a proton from the adjacent carbon to the carbocation. The resulting product is 2-methyl-2-butene. **Hint:** Compare the possible products and choose the one with the most alkyl substituents on the double bond. ### Final Answer The major product obtained from the dehydration of (CH₃)₂CHCH(CH₃)OH in the presence of acid is **2-methyl-2-butene**. ---
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