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Chapter 3: Q68P (page 138)

Which of the following conformers has the highest energy (is the least stable)?

Short Answer

Expert verified

Compound B has the highest energy and is the least stable.

Step by step solution

01

Step 1: The stereochemistry of the three conformers.

  • All three compounds are diaxial-substituted cyclohexane.
  • The two alternative chair conformations formed after a ring flip are not equally stable when a substituent is added to a cyclohexane ring.
02

The conformer that has the highest energy or is the least stable.

Conformer B has the highest energy and is least stable because:

  • It has di-axial interaction between CH3 and Cl.
  • Di-axial interaction between CH3and Cl is more than between Cl and H or between CH3 and H.

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Most popular questions from this chapter

a. Calculate the energy difference between the two chair conformers of trans-1,4-dimethylcyclohexane.

b. What is the energy difference between the two chair conformers of cis-1,4-dimethylcyclohexane?

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Ansaid and Motrin belong to the group of drugs known as nonsteroidal anti-inflammatory drugs (NSAIDs). Both are only slightly soluble in water, but one is a little more soluble than the other. Which of the drugs has the greater solubility in water?

One of the chair conformers of cis-1,3-dimethylcyclohexane is 5.4 kcal/mol less stable than the other. How much steric strain does a 1,3-diaxial interaction between two methyl groups introduce into the conformer?

Give each substituent on the nine-carbon chain a common name and a parenthetical name.
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