Classification and isomerism

MDCAT Chemistry · Chemistry · Fundamental principles of organic chemistry. The idea in plain words, the rules to remember, the mistake to avoid and a worked example, written and checked by Mega Lecture.

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The idea

Organic compounds are the compounds of carbon, apart from a few simple ones such as CO, CO2, carbonates and cyanides. They are classified by their carbon skeleton (open chain or ring) and by their functional group, the atom or group of atoms that gives a family its typical reactions. Compounds with the same functional group form a homologous series.

Isomers have the same molecular formula but a different arrangement of atoms. In structural isomers the atoms are joined in a different order. In stereoisomers the order is the same, but the arrangement in space is different.

Organic compounds come from coal, petroleum, natural gas and living things. Wöhler's preparation of urea in 1828 showed that they can also be made from inorganic substances.

Rules to remember

Common mistake

Students give cis-trans isomers to every alkene. If either carbon of the C=C carries two identical groups, as in CH2= or (CH3)2C=, there is only one form.

Worked example

How many isomers have the molecular formula C2H2Cl2, counting cis and trans forms separately?

  1. Both Cl atoms on one carbon: CH2=CCl2 (1,1-dichloroethene). Each carbon has two identical atoms, so there is no cis-trans pair: 1 isomer.
  2. One Cl on each carbon: CHCl=CHCl (1,2-dichloroethene). Each carbon has two different atoms, H and Cl, so cis and trans forms exist: 2 isomers.
  3. Total = 1 + 2 = 3.

Answer: Three isomers: 1,1-dichloroethene, cis-1,2-dichloroethene and trans-1,2-dichloroethene.

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