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GATE 2019 CY – Question 56

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. · 2 marks · Numerical answer

Pure (R)-2-bromobutane has specific rotation −112.00°. A sample rotates −82.88°. Find the percentage of (S)-(+)-enantiomer.

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Correct answer: 13 to 13

Explanation

The fractional enantiomeric excess in favour of R is 82.88/112=0.74. Let fractions be r and s: r+s=1 and r−s=0.74. Subtract to obtain 2s=0.26, hence s=0.13. The sample contains 13% S and 87% R; optical purity 74% is not the minor-enantiomer percentage.

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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 →