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Consider the following reaction sequence...

Consider the following reaction sequence
`H_(3)C-underset(CH_(3))underset(|)overset(CH_(3))overset(|)(C)-CH=CH_(2) underset(2." "KOH-EtOH, Heat)overset(1." "HBr)to`
the major product formed is

A

`H_(3)C-underset(CH_(3))underset(|)overset(CH_(3))overset(|)(C)-underset(OH)underset(|)(C)H-CH_(3)`

B

`H_(3)C-underset(OE t)underset(|)overset(CH_(3))overset(|)(C)-CH(CH_(3))_(2)`

C

`H_(3)C-underset(CH_(3))underset(|)overset(CH_(3))overset(|)(C)-CH=CH_(2)`

D

`H_(3)C-underset(CH_(3))underset(|)(C)=underset(CH_(3))underset(|)(C)-CH_(3)`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given reaction sequence, we will follow these steps: ### Step 1: Identify the Starting Material The starting material is 2-methyl-2-pentene, which can be represented as: \[ \text{H}_3C-\text{C}(\text{CH}_3)-\text{C}(\text{CH}_3)=\text{CH}_2 \] ### Step 2: Reaction with HBr When 2-methyl-2-pentene reacts with HBr, the double bond will react with HBr to form a carbocation. The HBr can add to the double bond in two ways: 1. H adds to the less substituted carbon (1° carbocation). 2. H adds to the more substituted carbon (2° carbocation). However, the more stable carbocation will be favored. In this case, the more stable 2° carbocation will form: \[ \text{CH}_3-\text{C}^+(\text{CH}_3)-\text{CH}_2-\text{Br} \] ### Step 3: Carbocation Rearrangement The formed 2° carbocation can undergo a rearrangement (methyl shift) to form a more stable 3° carbocation: \[ \text{CH}_3-\text{C}^+(\text{CH}_2-\text{CH}_3)-\text{CH}_3 \] ### Step 4: Nucleophilic Attack The bromide ion (Br⁻) will then attack the carbocation to form the product: \[ \text{CH}_3-\text{C}(\text{Br})(\text{CH}_2-\text{CH}_3)-\text{CH}_3 \] ### Step 5: Reaction with KOH (Ethanolic) The next step involves treating the product with KOH in ethanol, which acts as a strong base. The base will abstract a proton from the β-carbon (the carbon adjacent to the carbon bearing the Br). According to Zaitsev's rule, the base will preferentially remove the hydrogen from the carbon that has the most substituents (the carbon with fewer hydrogens). In this case, the elimination will occur as follows: 1. The base abstracts a hydrogen from the β-carbon that has fewer hydrogens. 2. The Br leaves, resulting in the formation of a double bond. ### Step 6: Final Product The final product after elimination will be: \[ \text{CH}_3-\text{C}(\text{CH}_3)=\text{C}(\text{CH}_2-\text{CH}_3) \] This is a more stable alkene. ### Summary of Major Product The major product formed from the reaction sequence is: \[ \text{CH}_3-\text{C}(\text{CH}_3)=\text{C}(\text{CH}_2-\text{CH}_3) \] ---
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