Compounds formed from P and Q are, respectively,
- AOptically active S and optically active pair (T, U).
- BOptically inactive S and optically inactive pair (T, U).
- COptically active pair (T, U) and optically active S.
- DOptically inactive pair (T, U) and optically inactive S.
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Correct answer: B
- Identify the isomeric dicarboxylic acids
Given molecular formula: .
A dicarboxylic acid with this formula and which decolorises must contain a bond. So the two geometrical isomers are:
- Maleic acid: cis-butenedioic acid
- Fumaric acid: trans-butenedioic acid
Their structures are:
- Use the anhydride clue to identify P
On heating, P forms a cyclic anhydride.
This is a characteristic property of maleic acid because in the cis-form the two groups are close enough to lose water intramolecularly and form a 5-membered cyclic anhydride.
Hence,
- Reaction with dilute alkaline
Cold dilute alkaline adds two groups across the double bond giving vicinal diols.
So both maleic acid and fumaric acid give 2,3-dihydroxysuccinic acid (tartaric acid type products), but stereochemistry differs.
- Product from P = maleic acid (cis alkene)
Syn addition of across cis-butenedioic acid gives:
For cis alkene + syn addition, the product is the meso tartaric acid form.
Meso tartaric acid is optically inactive due to internal plane of symmetry.
So product from P is:
- Product from Q = fumaric acid (trans alkene)
Syn addition of across trans-butenedioic acid gives:
But now stereochemistry leads to the enantiomeric pair:
- tartaric acid
- tartaric acid
These are optically active individually, but together form an optically inactive racemic pair.
Since the options mention pair , this corresponds to the enantiomeric pair. Thus the pair is considered optically inactive pair.
- Match with options
- From P: optically inactive
- From Q: optically inactive pair
Therefore the correct option is:
- Comparison with stored answer
Stored correct answer: B
My derived answer: B
So they agree.
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