The reaction begins with the protonation of the double bond in 3-chloro-1-butene by HCl. Following Markovnikov’s rule, the proton adds to the carbon with more hydrogen atoms, forming a secondary carbocation:
Step 2: Carbocation Rearrangement (Hydride Shift)
The initially formed secondary carbocation undergoes a 1,2-hydride shift to form a more stable tertiary carbocation:
Step 3: Nucleophilic Attack by Chloride Ion (\( \text{Cl}^- \))
Attack on the secondary carbocation:
Attack on the tertiary carbocation:
One meso compound
One pair of enantiomers
Total Possible Products:
From attack on the secondary carbocation: 1 product (\( \text{CH}_3\text{CHClCH}_2\text{CH}_2\text{Cl} \))
From attack on the tertiary carbocation: 3 products (\( \text{CH}_3\text{CHClCHClCH}_3 \), including a meso compound and a pair of enantiomers)
Total number of possible isomeric products: \( 1 + 3 = 4 \).
Final Answer:
The total number of possible isomeric products is 4.
are isomeric compounds. 
are functional group isomers.