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What is the major product when CH3–CH2–C≡CH reacts with HCl?

1. CH3–CH2–C=CH2 Cl
2. CH3–CH2–C=C–CH3 Cl
3. CH3–CH2–C≡CH Cl
4. CH3–CH2–CH=CH2 Cl

Correct answer: CH3–CH2–C=C–CH3 Cl

Solution

The addition of HCl to CH3–CH2–C≡CH follows Markovnikov's rule, where the hydrogen adds to the carbon with more hydrogens, and the chlorine adds to the other carbon, forming CH3–CH2–C=CH–Cl.

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