Understanding Addition Reactions of Alkenes

Expert reviewed 23 November 2024 5 minute read


Introduction

Alkenes are unsaturated hydrocarbons containing at least one carbon-carbon double bond (C=C). These molecules readily undergo addition reactions, where atoms or molecules add across the double bond to form saturated products. This article explores the four major types of alkene addition reactions: hydrohalogenation, halogenation, hydrogenation, and hydration.

Why Are Alkenes Reactive?

Alkenes are highly reactive due to their electron-rich double bond. The π-electrons in the C=C bond make alkenes excellent nucleophiles (electron-rich species that can attack electron-poor molecules). The carbon atoms in the double bond are each bonded to only three other atoms, allowing them to form additional bonds.

Types of Addition Reactions

1. Hydrohalogenation

Hydrohalogenation is the addition of a hydrogen halide (HX) across a double bond. The process follows these steps:

  • The hydrogen halide (HX) polarizes, creating an electrophilic H⁺
  • The alkene attacks this H⁺, forming a carbocation intermediate
  • The halide ion (X⁻) attacks the carbocation to form the final product

The reaction can be represented as:

RCH=CH2+HX>RCHXCH3{R-CH=CH2 + HX -> R-CHX-CH3}

Markovnikov's Rule

Markovnikov's rule predicts the major product of hydrohalogenation:

  • The H⁺ attaches to the carbon with more hydrogen atoms
  • The X⁻ attaches to the carbon with more alkyl groups

This can be explained by carbocation stability:

Tertiary(3°)>Secondary(2°)>Primary (1°) \text{Tertiary} (3°) > \text{Secondary} (2°) > \text{Primary } (1°)

2. Halogenation

Halogenation adds a halogen molecule (X2{X2}) across the double bond. This forms a dihalogenated product:

RCH=CH2+X2>RCHXCH2X{R-CH=CH2 + X2 -> R-CHX-CH2X}

3. Hydrogenation

Hydrogenation adds hydrogen (H2{H2}) across the double bond in the presence of a metal catalyst:

RCH=CH2+H2>[Pd/C]RCH2CH3{R-CH=CH2 + H2 ->[Pd/C] R-CH2-CH3}

Common catalysts include:

  • Palladium on carbon (Pd/C)
  • Platinum (Pt)
  • Nickel (Ni)

4. Hydration

Hydration adds water across the double bond in the presence of an acid catalyst:

RCH=CH2+H2O>[H+]RCHOHCH3{R-CH=CH2 + H2O ->[H+] R-CHOH-CH3}

Key features:

  • Requires dilute acid catalyst (H2SO4{H2SO4} or H3PO4{H3PO4})
  • Follows Markovnikov's rule
  • Forms an alcohol product

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