☰ Contents · Chemistry (Organic chemistry)

Alkynes. Acetylene

Lessons 15 · 1 lessons · A. Mutalibov, E. Murodov, S. Masharipov, H. Islomova. Organic Chemistry, Grade 10, 1st edition. G‘afur G‘ulom Publishing House, Tashkent, 2017
15

Alkynes: preparation and properties

Textbook: pp. 56–60
GoalExplain the structure, naming, preparation and properties of alkynes using acetylene.
New words
alkynes · alkinlartriple bond · uchbog‘hydration (Kucherov reaction) · gidratlanish (Kucherov)calcium carbide · kalsiy karbid
Explanation

Alkynes are open-chain unsaturated hydrocarbons with one C≡C triple bond; the general formula is CₙH₂ₙ₋₂ and the first member is acetylene (ethyne) HC≡CH. In systematic names “-ane” becomes “-yne” and the triple-bond position is numbered: propyne, butyne-1, butyne-2; numbering starts at the end nearer the triple bond. In rational nomenclature an alkyne is a derivative of acetylene: methylacetylene (propyne), dimethylacetylene (butyne-2). Alkynes are interclass isomers of alkadienes with the same carbon number. Acetylene is made from calcium carbide and water: CaC₂ + 2H₂O → C₂H₂↑ + Ca(OH)₂ or by heating methane at 1500 °C: 2CH₄ → C₂H₂ + 3H₂. It is a colourless gas, sparingly soluble in water and slightly lighter than air. In the Kucherov reaction water adds in the presence of mercury salts to give acetaldehyde: HC≡CH + H₂O → CH₃–CHO. N. D. Zelinsky passed acetylene over activated carbon to obtain benzene: 3C₂H₂ → C₆H₆. Acetylene adds H₂, Br₂ and HCl in two stages; burned in oxygen it reaches a flame temperature of about 3000 °C and is used for welding and cutting metals.

Worked examples
Alkynes for C₅H₈: pentyne-1 HC≡C–CH₂–CH₂–CH₃, pentyne-2 CH₃–C≡C–CH₂–CH₃, 3-methylbutyne-1 HC≡C–CH(CH₃)–CH₃ — 3 isomers.
32 g of CaC₂ (M = 64, 0.5 mol) gives 0.5 mol, i.e. 13 g, of acetylene with water. Burning needs 2.5 volumes of O₂ per volume of acetylene: 25 L of O₂ for 10 L of C₂H₂.
Class activity

Look up how acetylene is used in welding and write why welders wear protective goggles. Acetylene is explosive; making or burning it at home is strictly forbidden — only the teacher may demonstrate it.

Practice
1
What are the general formula and first member of alkynes?
2
How many grams of acetylene form from 96 g of calcium carbide (M(CaC₂) = 64, M(C₂H₂) = 26)?
3
How many litres of O₂ are needed to burn 10 L of acetylene (2C₂H₂ + 5O₂ → 4CO₂ + 2H₂O)?
4
Why does acetylene give a much hotter flame than a common fuel when burned in oxygen?