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GATE 2020 CY – Question 15

Organic Chemistry · Stereochemistry: Chirality and symmetry of organic molecules with or without chiral centres and determination of their absolute configurations and optical purity. Relative stereochemistry in compounds having more than one stereogenic centre. Homotopic, enantiotopic and diastereotopic atoms, groups and faces. Conformational analysis of acyclic and cyclic compounds. Geometrical isomerism and optical isomerism. Configurational and conformational effects, atropisomerism, and neighbouring group participation on reactivity and selectivity/specificity. Stereoselective and stereospecific synthesis. Enantiomeric excess. · 1 mark · Multiple choice

Find the absolute configurations at positions 4a and 8a of the compound shown.

Diagram for GATE 2020 CY question 15
  1. 4aR, 8aS
  2. 4aR, 8aR
  3. 4aS, 8aS
  4. 4aS, 8aR

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Correct answer: (D) 4aS, 8aR

Explanation

Apply CIP ordering separately at the two ring junctions, following each carbon path until the first difference and treating carbonyl double bonds by duplicate-atom rules. At 4a, OH has the highest priority; the carbonyl-containing path outranks the less substituted saturated path. At 8a, compare the carbonyl-bearing paths and the formyl substituent rather than ranking carbons by their visual position. Orient the lowest-priority group away using the drawn dashed bonds. The resulting descriptors are 4aS and 8aR, D.

More Stereochemistry: Chirality and symmetry of organic molecules with or without chiral centres and determination of their absolute configurations and optical purity. Relative stereochemistry in compounds having more than one stereogenic centre. Homotopic, enantiotopic and diastereotopic atoms, groups and faces. Conformational analysis of acyclic and cyclic compounds. Geometrical isomerism and optical isomerism. Configurational and conformational effects, atropisomerism, and neighbouring group participation on reactivity and selectivity/specificity. Stereoselective and stereospecific synthesis. Enantiomeric excess. questions

All Stereochemistry: Chirality and symmetry of organic molecules with or without chiral centres and determination of their absolute configurations and optical purity. Relative stereochemistry in compounds having more than one stereogenic centre. Homotopic, enantiotopic and diastereotopic atoms, groups and faces. Conformational analysis of acyclic and cyclic compounds. Geometrical isomerism and optical isomerism. Configurational and conformational effects, atropisomerism, and neighbouring group participation on reactivity and selectivity/specificity. Stereoselective and stereospecific synthesis. Enantiomeric excess. questions →