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How many stereogenic centers are there in the following tetrasubstituted adamantane molecule?
  • a)
    0
  • b)
    1
  • c)
    4
  • d)
    6
Correct answer is option 'B'. Can you explain this answer?
Verified Answer
How many stereogenic centers are there in the following tetrasubstitut...
The adamantane derivative features four asymmetric substituted carbon atoms, and it only exists as two stereoisomers (enantiomers) rather than the sixteen predicted by the 2n rule. However, the number of observed stereoisomers is only 2 since once the first stereocenter is defined, the remaining three are determined by their relative configuration.
The configurations of the asymmetric bridgehead carbon units in this structure are (R), (S), (R) and (R) respectively, for the Br, Cl, CO2H and CH3 substituents.
The central adamantyl residue may be regarded as an extended tetrahedron, and the stereogenic center is located in the center of the adamantyl cage, shown by the dotted lines below connecting at the center of the molecule, and the configuration shown here is (R).
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Most Upvoted Answer
How many stereogenic centers are there in the following tetrasubstitut...
The adamantane derivative features four asymmetric substituted carbon atoms, and it only exists as two stereoisomers (enantiomers) rather than the sixteen predicted by the 2n rule. However, the number of observed stereoisomers is only 2 since once the first stereocenter is defined, the remaining three are determined by their relative configuration.
The configurations of the asymmetric bridgehead carbon units in this structure are (R), (S), (R) and (R) respectively, for the Br, Cl, CO2H and CH3 substituents.
The central adamantyl residue may be regarded as an extended tetrahedron, and the stereogenic center is located in the center of the adamantyl cage, shown by the dotted lines below connecting at the center of the molecule, and the configuration shown here is (R).
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