Cis-Trans Isomers: Organic & Inorganic Compounds

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Shekhar Suman

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In Chemistry, when we are studying isomers, we will definitely come across various types of isomers. They are mainly divided into two groups namely constitutional isomers and stereoisomers. There are more sub-type of isomers. As such, cis and trans isomers are such type of isomers which we are going to learn here.

Read Also: Elimination Reaction

What are Isomers?

Isomers are molecules, compounds, or polyatomic ions which have an identical molecular formula with the same number of atoms but differ in the way in which they are arranged (i.e., differ in their structure from each other). The presence of isomers is called Isomerism. There are two types of isomers, that can further be divided:

  1. Structural isomers
  2. Stereoisomers

What are Cis-Trans Isomers?

Cis-Trans isomers are Stereoisomers that exhibit stereoisomerism. Cis-trans isomerism is also known as geometrical isomerism or configurational isomerism. The words “Cis” and “Trans” mean “This side of” and “other side of” in Latin context. Isomers that have their functional groups on the same side are called Cis-isomers and isomers that have their functional groups on the opposite sides are called Trans-isomers.

Structure of Cis-Trans Isomers:

Let R, H be two different functional groups. Consider a compound RHC=CHR. If observed in the below image Cis isomer has the functional groups R and H on the same side. Whereas in Trans isomer the functional groups are on the opposite side of the Carbon bond.

Examples of Cis-Trans Isomers:

Some examples of Cis-Trans Isomerism in organic and inorganic compounds is given below

Organic Compounds: The presence of a double or a triple bond in a molecule restricts the bond rotation within the molecule.

Inorganic Compounds:  Many diazines and diphosphates exhibit cis-trans isomerism. Based on the positions of ligands, coordinate complexes that have square planar or octahedral geometries also exhibit cis-trans-isomerism. It can be observed that similar ligands are positioned on the same side in cisplatin and on the opposite side in transplatin.

Cis Isomers Trans Isomers
Similar functional groups placed on the same side of the double bond Similar functional groups placed on the opposite side of the double bond
The molecules in cis isomers are loosely packed The molecules in trans isomers are tightly packed
Low melting point and high boiling point High melting point and low boiling point
Presence of strong attractive forces between atoms No presence of strong attractive force between atoms
Almost all Cis isomers are always polar Trans isomers are not always polar there are many non-polar trans isomers molecules
High acidic strength Low acidic strength because protons aren’t readily emitted
Strongly soluble content is present in inert solvents Solubility is smaller in neutral solvents

Properties of Cis-Trans Isomers:

  • Cis Isomers are mostly much reactive compared to Trans isomers.
  • Cis Isomer can reduce alkenes and alkynes to alkanes.
  • Cis Isomer can occur in organic as well as inorganic compounds
  • A molecule is said to be exhibiting cis-trans isomers only if all these three rules are satisfied:
  1. A restricted atom is present.
  2. Presence of two different functional groups individually in both the restricted atoms.
  3. At least one functional group is commonly present in both the restricted atoms.
  • Alkenes with more than two different substituents cannot use Cis-Trans notation.

Read Also: Class 12 Carbon and Its Compounds

Things to Remember:

  • Cis isomers have functional groups present on the same side of the bond whereas trans isomers have functional groups present on the opposite side of the bond.
  • Cis isomers have a higher boiling point because of the presence of strong attractive forces between the atoms of the cis isomer.
  • Trans isomers have a lower boiling point because of the absence of strong attractive forces between the atoms of Trans-isomer.
  • Cis isomers have a low melting point compared to trans isomers because the molecules are loosely packed in Cis isomers.
  • Trans isomers have a high melting point compared to cis isomers because the molecules are tightly packed in Cis isomers.

Sample Question on Cis-Trans Isomers:

Ques: Draw one structural isomer and one geometrical isomer? (2 marks)

Ans: 

Structural Isomer and Geometrical Isomer

Ques: Why do cis and trans isomers exhibit different properties? (2 marks)

Ans: In most cases, cis-trans isomers exhibit different physical properties. This may be due to the spatial arrangement of the atoms or due to the difference in the dipolar moment of the molecules.

Ques: Why do alkenes exhibit cis-trans isomerism? (1 mark)

Ans: There are restricted atoms in alkenes that contain different individual functional groups therefore alkenes exhibit cis-trans isomerism.

Ques: What is the most stable isomer? (1 mark)

Ans: Trans-1,2 - dimethyl cyclohexane is the most stable isomer because it has the most stable conformed.

Ques: Explain the Limitations of Cis-Trans Isomerism? (2 marks)

Ans: The cis-trans isomerism does not exist If all the restricted atoms have different functional groups. For example, let there be a compound xwC = Cyz. Here different functional groups x, w, and y, z is present but, there is no identical functional group. So, this compound cannot have cis-trans isomerism.

Ques: What is E-Z Notation?

Ans: In E-Z Nomenclature, we only consider two substituents that have the highest priority according to the Cahn–Ingold–Prelog (CIP) sequence rules. The E in E-Z convention represents “entgegen” which means “opposite” in German and Z represents “zusammen” which means “together” in German.

Ques: How is E-Z Nomenclature different from the Cis-Trans Notation? (2 marks)

Ans: The cis-trans convention works unambiguously when at least one pair of identical substituent groups on the carbons exists. Lets, take the example of 1-Bromo-2-chloro-1-fluoro ethane. As the cis-trans system uses relative stereochemistry between two atoms hence, we cannot use Cis-Trans Notation here. This makes the nomenclature of naming difficult to read. Hence the concept of E-Z Nomenclature comes into light which is based on absolute stereochemistry.

Ques: Draw the structures for cis-3-heptene and trans-3-heptene. (2 marks)

Ans: 

cis-3-heptene and trans-3-heptene

Ques: Mention Boiling points and Melting points of Some carbon compounds? (2 marks)

Ans:

Compound Boiling point (k) Melting point (k)
Chloroform (CHCl3 ) 334 209
Acetic acid (CH3COOH) 391 290
Methane (CH4 ) 111 90
Ethanol (CH3CH2OH) 351 156

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