☰ Contents · Chemistry (Organic chemistry)

Isomerism and its types

Lessons 3 · 1 lessons · A. Mutalibov, E. Murodov, S. Masharipov, H. Islomova. Organic Chemistry, Grade 10, 1st edition. G‘afur G‘ulom Publishing House, Tashkent, 2017
3

Isomerism and its types

Textbook: pp. 11–14
GoalDistinguish the types of isomerism (chain, position, interclass, geometric) and write isomer structures.
New words
isomers · izomerlarchain isomerism · zanjir izomeriyasiinterclass isomerism · sinflararo izomeriyacis-/trans- isomerism · sis-, trans-izomeriya
Explanation

Substances with the same molecular formula but different structure and properties are isomers, and the phenomenon is isomerism; the term was introduced in the 1830s by J. Berzelius. In chain isomerism the carbon skeleton differs: C₄H₁₀ has n-butane and 2-methylpropane (isobutane), C₅H₁₂ has three isomers, hexane has 5 and heptane has 9. In position isomerism the functional group or double (triple) bond sits on different carbons: 1-chlorobutane and 2-chlorobutane, butene-1 and butene-2, propanol-1 and propanol-2. In interclass isomerism the formula is the same but the compounds belong to different classes: C₂H₆O fits both ethanol (alcohol) and dimethyl ether; C₃H₆O fits propanal (aldehyde) and propanone (ketone). Geometric isomerism arises because rotation about a double bond is impossible: if each double-bonded carbon carries two different substituents, the substituents can lie on the same side (cis-) or opposite sides (trans-).

Worked examples
The three isomers of C₅H₁₂: n-pentane CH₃–CH₂–CH₂–CH₂–CH₃; 2-methylbutane CH₃–CH(CH₃)–CH₂–CH₃; 2,2-dimethylpropane C(CH₃)₄. This is chain isomerism.
In butene-2 CH₃–CH=CH–CH₃ each double-bonded carbon carries H and CH₃, so cis- and trans- isomers exist. In propene CH₂=CH–CH₃ carbon 1 has two identical H atoms, so there are no geometric isomers.
Class activity

Using two colours of plasticine balls and sticks, assemble all three isomers of C₅H₁₂ and sort them by the length of their longest chain. Work with sticks under adult supervision.

Practice
1
How many isomers exist for C₄H₁₀?
2
Add the numbers of isomers of hexane and heptane.
3
What type of isomerism do butanol-1 and butanol-2 show?
4
Why does pentene-1 have no cis-/trans- isomers while pentene-2 does?