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Q6.19(x):
How the following conversions can be carried out? (x) 2-Methyl-1-propene to 2-chloro-2-methylpropane

Solution :

Step 1: Analyzing Reactants and Products

The starting material is 2-methyl-1-propene ($CH_3-C(CH_3)=CH_2$), an alkene. The target molecule is 2-chloro-2-methylpropane ($CH_3-C(Cl)(CH_3)-CH_3$), an alkyl halide. The conversion requires the addition of hydrogen chloride ($HCl$) across the carbon-carbon double bond.

Step 2: Theoretical Foundation

The addition of hydrogen halides to unsymmetrical alkenes follows Markownikoff’s Rule. According to this rule, the negative part of the addendum ($Cl^-$) attaches itself to the carbon atom of the double bond that carries the lesser number of hydrogen atoms [Per Markownikoff’s Rule].

Step 3: Reaction Mechanism

The reaction proceeds via the formation of a stable carbocation intermediate:

  • Protonation: The electrophile $H^+$ from $HCl$ attacks the double bond to form the more stable tertiary ($3^\circ$) carbocation ($CH_3-C^+(CH_3)-CH_3$). [Per Electrophilic Addition Mechanism].
  • Nucleophilic Attack: The nucleophile $Cl^-$ attacks the tertiary carbocation to form 2-chloro-2-methylpropane.

Step 4: Chemical Equation

The chemical transformation is represented as follows:

$CH_3-C(CH_3)=CH_2 + HCl \xrightarrow{\text{Room Temperature}} CH_3-C(Cl)(CH_3)-CH_3$

CH3-C(CH3)=CH2 + HCl CH3-C(Cl)(CH3)-CH3

Step 5: Comparative Analysis

Property Reactant (2-Methyl-1-propene) Product (2-Chloro-2-methylpropane)
Functional Group Alkene ($C=C$) Alkyl Halide ($C-Cl$)
Hybridization of C-2 $sp^2$ $sp^3$
Reagent Used N/A $HCl$ (Dry)

Final Solution: The conversion of 2-methyl-1-propene to 2-chloro-2-methylpropane is achieved by the electrophilic addition of hydrogen chloride ($HCl$), where the chloride ion follows Markownikoff’s rule to form the stable $3^\circ$ carbocation intermediate.


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