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BITSAT2018ChemistryGeneral Organic ChemistryActual

Which of the following is the correct order of stability of conformations for NH 2 - CH 2 - CH 2 - OH .

Options

  1. Agauche > eclipsed > anti
  2. Bgauche > anti > eclipsed
  3. Ceclipsed > gauche > anti
  4. Danti > eclipsed > gauche

Correct answer

B. gauche > anti > eclipsed

Step-by-step solution

The anti conformation is most stable in which NH 2 and OH groups are far apart as possible and minimum repulsion between two groups occurs. In fully eclipsed conformation NH 2 and OH groups are so close that the steric strain is maximum. Since, gauche form is stabilised by intermolecular hydrogen bonding, hence it is more stable than anti.

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