The compound R is- A

- B

- C

- D

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Correct answer: A
Step 1: Identification of Compound P
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Molecular Formula and Functional Group: The compound P has the molecular formula and is an organic acid, which implies the presence of a carboxylic acid group ().
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Oxidation Product: P can be easily oxidized to a dibasic acid which reacts with ethylene glycol to produce the polymer dacron. Dacron is a polyester formed from the condensation of terephthalic acid (benzene-1,4-dicarboxylic acid) and ethylene glycol. This strongly indicates that the dibasic acid is terephthalic acid.
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Structure of P: Since P oxidizes to terephthalic acid, P must be a para-substituted benzoic acid. The structure can be represented as , where R is a side chain that can be oxidized to a group.
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Side Chain Formula: Let's determine the formula of the side chain R.
- The formula of the part is .
- Subtracting this from the molecular formula of P ():
- So, the side chain R has the formula .
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Degree of Unsaturation (DoU): For , the DoU is . A benzene ring accounts for 4 DoU and the carbonyl group () in the carboxylic acid accounts for 1 DoU. This leaves DoU for the side chain , which means it must contain a double bond or a ring.
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Ozonolysis: The problem states that ozonolysis of P gives an aliphatic ketone as one of the products. Ozonolysis cleaves C=C double bonds. For an aliphatic ketone to be formed as a separate molecule, the structure of the side chain attached to the ring must be of the form . Ozonolysis (, then reductive workup with ) would yield and (a ketone).
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Structure of the Side Chain: The side chain is . We need to find and such that the total structure has 4 carbons and 7 hydrogens. The ketone formed is . The simplest aliphatic ketone is acetone, . If the ketone is acetone, then and .
- Let's check the formula for the side chain : It has carbon atoms and hydrogen atoms. The formula is . This matches our requirement.
- Thus, the side chain is the 2-methylprop-1-enyl group.
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Final Structure of P: Combining all the information, the structure of P is 4-(2-methylprop-1-enyl)benzoic acid.
Step 2: Reaction Sequence to form R
- P to intermediate: P reacts with thionyl chloride (). This reagent converts a carboxylic acid into an acid chloride.
- Intermediate to Q: The resulting acid chloride undergoes Friedel-Crafts acylation with benzene in the presence of anhydrous . The acyl group attaches to the benzene ring to form a ketone, Q.
Structure of Q is (4-(2-methylprop-1-enyl)phenyl)(phenyl)methanone.
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Q to R: Compound Q is treated with over a Palladium-Carbon catalyst (). Catalytic hydrogenation reduces both the carbon-carbon double bond and the ketone group. The reduction of a diaryl ketone like this one under these conditions typically leads to the corresponding methylene group (), a reaction known as hydrogenolysis.
- Reduction of the C=C bond: (isobutyl group)
- Reduction of the C=O group: (methylene bridge)
So, the final product R is:
Step 3: Comparison with Options
Let's examine the given options:
- Option A: This structure matches our derived structure for R, which is 1-benzyl-4-isobutylbenzene.
- Option B: The bridge between the two rings is , which is incorrect.
- Option C: The isobutyl group is attached to the wrong benzene ring. The side chain was originally on the ring derived from benzoic acid.
- Option D: The substituents are incorrect.
Therefore, the correct structure for compound R is given in option A.
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