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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

What is each compound’s systematic name?

a. Which of the following compounds forms hydrogen bonds between its molecules?

1. CH3CH2OCH2CH2OH 3. CH3CH2CH2CH2Br 5. CH3CH2CH2COOH

2. CH3CH2N(CH3)2 4. CH3CH2CH2NHCH3 6. CH3CH2CH2CH2F

b. Which of the preceding compounds forms hydrogen bonds with a solvent such as ethanol?

Draw the structures and provide systematic names for parts a, b, and c by substituting a chlorine for a hydrogen of methylcyclohexane:

a. A primary alkyl halide

b. A tertiary alkyl halide

c. Three secondary alkyl halides

a. What is each compound’s systematic name?

b. Draw a skeletal structure for each condensed structure given and draw a condensed structure for each skeletal structure.

Draw the most stable conformer of the following molecule. (A solid wedge points out of the plane of the paper toward the viewer. A hatched wedge points back from the plane of the paper away from the viewer.)
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