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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. Draw a potential energy diagram for rotation about the C-C bond of 1,2-dichloroethane through 360degree, starting with the least stable conformer. The anti-conformer is 1.2 kcal/mol more stable than a gauche conformer. A gauche conformer has two energy barriers, 5.2 kcal/mol and 9.3 kcal/mol.

b. Draw the conformer that is present in greatest concentration.

c. How much more stable is the most stable staggered conformer than the most stable eclipsed conformer?

d. How much more stable is the most stable staggered conformer than the least stable eclipsed conformer?

What is each compound’s systematic name?

Draw the condensed and skeletal structures for each of the following amines:

a. 2-methyl-N-propyl-1-propanamine d. methyldipropylamine

b. N-ethylethanamine e. N,N-dimethyl-3-pentanamine

c. 5-methyl-1-hexanamine f. cyclohexylethylmethylamine

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?

Using Newman projections, draw the most stable conformer for each of the following:

a. 3-methylpentane, viewed along the C-2 - C-3bond

b. 3-methylhexane, viewed along the C-3 - C-4bond

c. 3,3-dimethylhexane, viewed along the C-3 - C-4bond
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