☰ Contents · Chemistry (Organic chemistry)

Physical and chemical properties of alkenes

Lessons 13 · 1 lessons · A. Mutalibov, E. Murodov, S. Masharipov, H. Islomova. Organic Chemistry, Grade 10, 1st edition. G‘afur G‘ulom Publishing House, Tashkent, 2017
13

Physical and chemical properties of alkenes

Textbook: pp. 50–52
GoalWrite the physical and chemical properties of alkenes (addition, oxidation, polymerization) as reaction equations.
New words
Markovnikov’s rule · Markovnikov qoidasipolymerization · polimerlanishmonomer · monomerbromine water · brom suvi
Explanation

Ethylene is a colourless, almost odourless gas (with a very faint sweetish smell), slightly lighter than air and sparingly soluble in water; C₂–C₄ alkenes are gases under ordinary conditions, and as the chain grows the members become liquids and then solids. The π-bond of the double bond governs the properties, so addition reactions are typical. Hydrogenation: CH₂=CH₂ + H₂ → CH₃–CH₃ (Ni, heat). Halogenation: CH₂=CH₂ + Br₂ → CH₂Br–CH₂Br; bromine water is decolourized, which is the qualitative test for unsaturation. Addition of hydrogen halides and water follows Markovnikov’s rule: hydrogen adds to the double-bond carbon that already has more hydrogens, and the halogen (or –OH) to the carbon with fewer: CH₂=CH–CH₃ + HBr → CH₃–CHBr–CH₃. Oxidation: with neutral KMnO₄ solution 3CH₂=CH₂ + 2KMnO₄ + 4H₂O → 3CH₂OH–CH₂OH + 2MnO₂ + 2KOH and the purple colour disappears; combustion: C₂H₄ + 3O₂ → 2CO₂ + 2H₂O. In polymerization monomer molecules join to form a polymer: nCH₂=CH₂ → (–CH₂–CH₂–)ₙ polyethylene; propene gives polypropylene, and n is the degree of polymerization.

Worked examples
Propene + HBr: CH₂=CH–CH₃ + HBr → CH₃–CHBr–CH₃ (2-bromopropane) — by Markovnikov’s rule Br goes to C-2, which has fewer hydrogens. 2-methylpropene + H₂O → (CH₃)₃C–OH (a tertiary alcohol).
28 g of ethylene (1 mol) with bromine: C₂H₄ + Br₂ → C₂H₄Br₂; 1 mol Br₂ = 160 g is used and 188 g of 1,2-dibromoethane forms. If polyethylene has M = 56000 g/mol, n = 56000 : 28 = 2000.
Class activity

Read the recycling marks (PE, PP, PVC) on plastic items and list which are polymers of ethylene or propene. No chemical experiments; never burn plastics.

Practice
1
What is the qualitative test for alkenes and what is observed?
2
Which product is the main one when HBr adds to 2-methylpropene?
3
Polyethylene has M = 84000 g/mol. What is the degree of polymerization n (M(C₂H₄) = 28)?
4
Why do alkenes decolourize KMnO₄ solution while alkanes do not?