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CH(3)-CH=CH-CH(2)-CH(3) overset(HI)to un...

`CH_(3)-CH=CH-CH_(2)-CH_(3) overset(HI)to underset("major")A`
Compound A is

A

`CH_(3)-CH_(2)-underset(|)underset(|)CH-CH_(2)-CH_(3)`

B

`CH_(3)-underset(|)underset(|)CH-CH_(2)-CH_(2)-CH_(3)`

C

`CH_(3)-underset(|)underset(|)overset(CH_(2))overset(|)C-CH_(2)-CH_(3)`

D

`CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-CH_(2)I`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to determine the major product (Compound A) formed when 1-pentene (CH₃-CH=CH-CH₂-CH₃) reacts with hydrogen iodide (HI). ### Step-by-Step Solution: 1. **Identify the Reactants**: The reactant is 1-pentene (CH₃-CH=CH-CH₂-CH₃) and it reacts with hydrogen iodide (HI). 2. **Protonation of the Alkene**: The double bond in 1-pentene is attacked by the proton (H⁺) from HI. This can occur at either of the carbon atoms involved in the double bond: - If the first carbon (C1) of the double bond is protonated, we get a carbocation at C2. - If the second carbon (C2) of the double bond is protonated, we get a carbocation at C1. 3. **Formation of Carbocations**: - **Carbocation from C1 protonation**: CH₃-CH(+)-CH₂-CH₂-CH₃ (2° carbocation at C2) - **Carbocation from C2 protonation**: CH₃-CH₂-CH(+)-CH₂-CH₃ (2° carbocation at C1) 4. **Stability of Carbocations**: - The stability of carbocations can be evaluated based on hyperconjugation and inductive effects. - The carbocation formed by protonating C1 has 3 alpha hydrogens available for hyperconjugation. - The carbocation formed by protonating C2 has 2 alpha hydrogens available for hyperconjugation. - Therefore, the carbocation at C2 (from protonation at C1) is more stable due to having more alpha hydrogens (3 vs. 2). 5. **Nucleophilic Attack by Iodide Ion**: The more stable carbocation (at C2) will be attacked by the iodide ion (I⁻) to form the final product. 6. **Final Product (Compound A)**: The major product (Compound A) is formed as follows: - The structure of Compound A will be CH₃-CH₂-CH(I)-CH₂-CH₃. ### Conclusion: The major product (Compound A) formed from the reaction of 1-pentene with HI is **CH₃-CH₂-CH(I)-CH₂-CH₃**. ---
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