JEE Challenger
More from Organic Chemistry - Basic Principles

Relationship Between Keto Enol Forms and Geometric Isomers

The correct statement(s) concerning the structures E\mathbf{E}, F\mathbf{F} and G\mathbf{G} is (are)

Diagram 0

Options

A

E\mathbf{E}, F\mathbf{F} and G\mathbf{G} are resonance structures

B

E\mathbf{E}, F\mathbf{F} and E\mathbf{E}, G\mathbf{G} are tautomers

Correct
C

F\mathbf{F} and G\mathbf{G} are geometrical isomers

Correct
D

F\mathbf{F} and G\mathbf{G} are diastereomers

Correct

Step-by-Step Solution

To determine the correct statements concerning the structures E\mathbf{E}, F\mathbf{F}, and G\mathbf{G}:

  1. Relation between E\mathbf{E}, F\mathbf{F}, and G\mathbf{G} (Tautomerism vs Resonance):

    • Structure E\mathbf{E} is a ketone (keto form).
    • Structures F\mathbf{F} and G\mathbf{G} are enols (enol forms) differing in the connectivity of hydrogen and the position of the double bond:
      Keto form (E)⇌Enol forms (F and G)\text{Keto form } (\mathbf{E}) \rightleftharpoons \text{Enol forms } (\mathbf{F} \text{ and } \mathbf{G})
    • Since the interconversion involves the migration of a proton accompanied by a shift of a π\pi-bond (change in atomic connectivity), E\mathbf{E} and F\mathbf{F}, as well as E\mathbf{E} and G\mathbf{G}, are tautomers (structural isomers in dynamic equilibrium), not resonance structures (which differ only in electron distribution).
    • Therefore, statement (A) is incorrect and statement (B) is correct.
  2. Relation between F\mathbf{F} and G\mathbf{G} (Geometrical Isomerism and Diastereomerism):

    • Both F\mathbf{F} and G\mathbf{G} are stereoisomers with restricted rotation about the carbon-carbon double bond (C=C\text{C}=\text{C}).
    • In structure F\mathbf{F}, the −OH-\text{OH} group and the top substituent are oriented on the same side (or relative spatial arrangement), whereas in G\mathbf{G}, their spatial orientation across the double bond is reversed (one is (E)(E)-isomer and the other is (Z)(Z)-isomer).
    • Because they differ in the spatial arrangement of atoms around the rigid double bond and are non-superimposable non-mirror images, F\mathbf{F} and G\mathbf{G} are geometrical isomers.
    • All geometrical isomers that are non-mirror images are, by definition, diastereomers.
    • Therefore, statements (C) and (D) are correct.

Thus, the correct statements are B, C, and D.