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Question

Consider the following statements with respect to citral
(A). Geranial and Neral are geometrical isomers of citral.
(B). It forms geranic acid on heating with potassium hydrogen sulphate.
(C). It gives 6-methylhept-5-en-2-one on treating with potassium carbonate.
(D). On oxidation with silver oxide it yields Laevulic acid.
Choose the correct answer from the options given below:

The correct answer is
(A) and (C) only

Citral is an important organic compound known for its characteristic lemon scent. It is found in the oils of lemon grass, lemon myrtle, and lemon trees. This question tests the understanding of its chemical properties, specifically its isomerism and reactions.

Citral's Geometrical Isomers: Geranial and Neral

Statement (A) claims that Geranial and Neral are geometrical isomers of Citral. Citral is actually a mixture of two geometrical isomers:

  • Geranial: This is the trans (E) isomer of citral.
  • Neral: This is the cis (Z) isomer of citral.

These isomers differ in the configuration around the double bond located between the second and third carbon atoms (C2=C3) of the molecule. Since they have the same molecular formula and connectivity but differ in the spatial arrangement around a double bond, they are indeed geometrical isomers. Therefore, statement (A) is correct.

Citral Reaction with Potassium Hydrogen Sulphate

Statement (B) suggests that Citral forms geranic acid upon heating with potassium hydrogen sulphate. Geranic acid is formed when the aldehyde group of citral is oxidized to a carboxylic acid group. While oxidation is the pathway to geranic acid, heating citral with potassium hydrogen sulphate typically promotes cyclization reactions or dehydration, rather than direct formation of geranic acid. Therefore, statement (B) is incorrect.

Citral Reaction Yielding 6-methylhept-5-en-2-one

Statement (C) states that Citral gives 6-methylhept-5-en-2-one on treating with potassium carbonate. Potassium carbonate is a mild base and can participate in various organic reactions. While this specific transformation might not be among the most common textbook examples, citral's reactivity, including its unsaturated aldehyde structure, allows for various base-catalyzed reactions. Accepting this statement as correct based on the provided options is necessary for selecting the right answer.

Oxidation of Citral with Silver Oxide

Statement (D) proposes that oxidation of Citral with silver oxide yields Laevulic acid. Silver oxide (Ag₂O), especially in the presence of ammonia (as in Tollens' reagent), is a mild oxidizing agent primarily used to oxidize aldehydes to carboxylic acids. In the case of citral, this would lead to the formation of geranic acid. It does not typically cause cleavage of the carbon-carbon double bonds to yield a molecule like Laevulic acid (4-oxopentanoic acid). Therefore, statement (D) is incorrect.

Conclusion

Based on the analysis of each statement:

  • Statement (A) is correct.
  • Statement (B) is incorrect.
  • Statement (C) is considered correct in the context of the question.
  • Statement (D) is incorrect.

Therefore, the correct combination of statements is (A) and (C) only.

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Important Questions from Chemistry (CUET PG) Mixed

  1. The final product (P) is

  2. Which correct sequence of reactions are applied to achieve the following transformation?
     

  3. Above conversion is carried out using
     

  4. The final product (D) in the above conversion is

  5. The major product (P) in the following transformation is

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