Draw all three staggered conformations for the following compound, viewed along the C₂-C3 bond. Determine which conformation is the most stable, taking into account gauche interactions and hydrogen-bonding interactions. (J. Phys. Chem. A 2001, 105, 6991-6997) Provide a reason for your choice by identifying all of the interactions that led to your decision. H H&COH C₂ C3 HỌ CH CH3 Which of the following is the most stable staggered conformer? Me H OH Me OH Me- Me Me H Conformer A OH OH OH HO H H H Conformer B Conformer C Me Conformer B because the anti OH groups avoid hydrogen bonding, which is a destabilizing effect. Conformer A because there are only two gauche interactions, and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer C because there is no steric strain for Me-OH gauche interactions and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer B because the large OH groups are anti to each other.

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Chapter3: The Chemistry Of Life: Organic Compounds
Section: Chapter Questions
Problem 2TYU: VISUALIZE The structures depicted are (a) enantiomers (b) different views of the same molecule (c)...
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Draw all three staggered conformations for the following compound, viewed along the C₂-C3 bond. Determine which conformation is
the most stable, taking into account gauche interactions and hydrogen-bonding interactions. (J. Phys. Chem. A 2001, 105, 6991-6997)
Provide a reason for your choice by identifying all of the interactions that led to your decision.
H
H&COH
C₂
C3
HỌ CH
CH3
Which of the following is the most stable staggered conformer?
Me
H
OH
Me
OH
Me-
Me
Me
H
Conformer A
OH
OH
OH
HO
H
H
H
Conformer B
Conformer C
Me
Conformer B because the anti OH groups avoid hydrogen bonding, which is a destabilizing effect.
Conformer A because there are only two gauche interactions, and hydrogen bonding between the two OH groups is a
stabilizing effect.
Conformer C because there is no steric strain for Me-OH gauche interactions and hydrogen bonding between the two OH
groups is a stabilizing effect.
Conformer B because the large OH groups are anti to each other.
Transcribed Image Text:Draw all three staggered conformations for the following compound, viewed along the C₂-C3 bond. Determine which conformation is the most stable, taking into account gauche interactions and hydrogen-bonding interactions. (J. Phys. Chem. A 2001, 105, 6991-6997) Provide a reason for your choice by identifying all of the interactions that led to your decision. H H&COH C₂ C3 HỌ CH CH3 Which of the following is the most stable staggered conformer? Me H OH Me OH Me- Me Me H Conformer A OH OH OH HO H H H Conformer B Conformer C Me Conformer B because the anti OH groups avoid hydrogen bonding, which is a destabilizing effect. Conformer A because there are only two gauche interactions, and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer C because there is no steric strain for Me-OH gauche interactions and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer B because the large OH groups are anti to each other.
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