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Biomolecules question

2019 · 10 Apr · Shift 2 · Q18
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Biomolecules question

2019 · 10 Apr · Shift 2 · Q18

JEE MainChemistryBiomoleculesMCQ+4 / −1
Number of stereo centers present in linear and cyclic structures of glucose are respectively :
  1. A
    4 & 4
  2. B
    4 & 5
  3. C
    5 & 4
  4. D
    5 & 5
View written solutionFree

Correct answer: B

  1. Linear (open-chain) glucose

    The structure of glucose in open-chain form is: CHO−CH(OH)−CH(OH)−CH(OH)−CH(OH)−CH2OH\text{CHO} - \text{CH(OH)} - \text{CH(OH)} - \text{CH(OH)} - \text{CH(OH)} - \text{CH}_2\text{OH}CHO−CH(OH)−CH(OH)−CH(OH)−CH(OH)−CH2​OH

    Now identify stereocenters:

    • C1C_1C1​ is an aldehyde carbonyl carbon, so it is not chiral.
    • C2,C3,C4,C5C_2, C_3, C_4, C_5C2​,C3​,C4​,C5​ are each attached to four different groups, so all are stereocenters.
    • C6C_6C6​ is CH2OH\text{CH}_2\text{OH}CH2​OH, so it is not chiral.

    Therefore, number of stereocenters in linear glucose is: 444

  2. Cyclic glucose

    In cyclic form, glucose forms a hemiacetal by reaction of the C1C_1C1​ aldehyde group with the C5C_5C5​ hydroxyl group.

    This creates a new chiral center at anomeric carbon C1C_1C1​.

    In the cyclic form:

    • C1C_1C1​ becomes chiral
    • C2,C3,C4,C5C_2, C_3, C_4, C_5C2​,C3​,C4​,C5​ remain chiral

    Hence total stereocenters in cyclic glucose are: 555

  3. Compare with options

    • A: 4&44 \& 44&4 ❌
    • B: 4&54 \& 54&5 ✅
    • C: 5&45 \& 45&4 ❌
    • D: 5&55 \& 55&5 ❌
  4. Final Answer

    The number of stereocenters in linear and cyclic glucose are respectively: 4 and 54 \text{ and } 54 and 5

    So, the correct option is B.

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