JEE AdvancedChemistryAldehydes Ketones and Carboxylic AcidsMCQ+3 / −1
In the following reaction sequence, the correct structure of E, F and G are : 

- A

- B

- C

- D

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Correct answer: C
The user has provided a multi-step organic reaction sequence and asked to identify the structures of the products E, F, and G.
Let's analyze the reaction sequence step by step.
Step 1: Formation of E
Reaction: Benzene reacts with and in the presence of anhydrous and .
- This is the Gattermann-Koch reaction, which is a method for formylation of aromatic rings.
- The reagents , , and generate the electrophile, the formyl cation or a complex that acts as its equivalent.
- This electrophile attacks the benzene ring in an electrophilic aromatic substitution reaction to introduce a formyl group ().
- Therefore, the product E is Benzaldehyde.
Step 2: Formation of F
Reaction: Compound E (Benzaldehyde) reacts with acetone () in the presence of dilute .
- This is a crossed aldol condensation reaction, specifically a Claisen-Schmidt condensation.
- Benzaldehyde has no -hydrogens, so it cannot form an enolate. Acetone has acidic -hydrogens.
- The base () abstracts an -hydrogen from acetone to form a nucleophilic enolate ion ().
- The enolate ion attacks the electrophilic carbonyl carbon of benzaldehyde.
- An intermediate -hydroxy ketone is formed, which readily undergoes dehydration (loss of a water molecule) upon gentle heating or even under the reaction conditions to form a more stable, conjugated system.
- The final product is an -unsaturated ketone.
- The product F is 4-phenylbut-3-en-2-one, also known as benzylideneacetone.
Step 3: Formation of G
Reaction: Compound F (4-phenylbut-3-en-2-one) is treated with .
- (Sodium borohydride) is a mild and selective reducing agent.
- It reduces aldehydes and ketones to their corresponding alcohols.
- Crucially, does not typically reduce carbon-carbon double bonds, especially when they are part of a conjugated system (it is not a strong enough hydride donor).
- Therefore, will reduce the ketone group () in F to a secondary alcohol ( ) while leaving the carbon-carbon double bond () intact.
- The product G is 4-phenylbut-3-en-2-ol.
Conclusion
Based on the analysis:
- E is Benzaldehyde ()
- F is 4-phenylbut-3-en-2-one ()
- G is 4-phenylbut-3-en-2-ol ()
Comparing these structures with the given options:
- Option A: F is the non-dehydrated aldol product, and G is derived from it. This is less likely as dehydration is highly favorable.
- Option B: E is incorrect (shows benzoic acid).
- Option C: The structures for E, F, and G match our derived structures perfectly.
- Option D: G is incorrect. It shows the reduction of both the C=C and C=O bonds, which is not characteristic of .
Therefore, Option C represents the correct structures for E, F, and G.
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