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Q8.15:

What is the relationship between the members of following pairs of structures ? Are they structural or geometrical isomers or resonance contributors ?

(a) 

Solution :

Step 1: Structural Analysis of Molecule A

The first structure provided is $CH_3-CH_2-CH=CH_2$.

  • IUPAC Name: But-1-ene
  • Molecular Formula: $C_4H_8$
  • Connectivity: The double bond is positioned between carbon-1 and carbon-2. The chain is a straight-chain alkene. [Per IUPAC nomenclature rules for unsaturated hydrocarbons].

Step 2: Structural Analysis of Molecule B

The second structure provided is $CH_3-CH=CH-CH_3$.

  • IUPAC Name: But-2-ene
  • Molecular Formula: $C_4H_8$
  • Connectivity: The double bond is positioned between carbon-2 and carbon-3. The chain remains a straight-chain alkene. [Per IUPAC numbering priority, ensuring the lowest locant for the functional group].

Step 3: Determination of Isomeric Relationship

To classify the relationship, we evaluate the following criteria:

  • Molecular Formula: Both compounds possess the formula $C_4H_8$. They are isomers.
  • Structural vs. Geometrical: The compounds differ in the position of the functional group (the double bond). Molecule A has the bond at $C_1$, while Molecule B has the bond at $C_2$.
  • Conclusion: Since the connectivity of the atoms has changed (the position of the $\pi$-bond is different), these are categorized as position isomers, which is a sub-category of structural isomers.

Step 4: Visualizing the Structural Distinction

But-1-ene: $CH_3-CH_2-CH=CH_2$ But-2-ene: $CH_3-CH=CH-CH_3$

Step 5: Theoretical Justification

By definition, Position Isomerism occurs when two or more compounds with the same molecular formula differ in the position of a functional group or a substituent on the carbon skeleton [Reference: Organic Chemistry Principles of IUPAC Nomenclature]. Because the double bond is a functional group, shifting its position from $C_1$ to $C_2$ satisfies the definition of structural isomers specifically known as position isomers. They are not resonance contributors because resonance requires the shifting of $\pi$-electrons without moving atomic nuclei [Per Valence Bond Theory].

Final Solution: The members of the pair are structural isomers, specifically categorized as position isomers.


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