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Chapter 4: Q.46. (page 128)

Question: Considering rotation around the bond highlighted in pink in each compound, draw Newman projections for the most stable and least stable conformations.

a.

b.

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Conformation

The conformation is the molecule's structure, which is obtained by the rotation of the single bond in the molecules.

02

Eclipsed conformation

The eclipsed conformation is obtained when the two substituents on the two corresponding carbon atoms have zero-degree angles or overlap.

The eclipsed conformation is always higher in energy compared to the staggered conformation.

03

Staggered conformation

The staggered conformation is obtained when the two substituents on the two corresponding carbon atoms have a600 angle.

04

Explanation

a.

The Newman projection of the given molecule is shown as:

Newman projection

b.

The Newman projection of the given molecule is shown as:

Newman projection

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Most popular questions from this chapter

Question: Label the sites of torsional and steric strain in each conformation.

a.

b.

c.

Question: For each compound drawn below:

a. Label each OH, Br, andCH3group as axial or equatorial.

b. Classify each conformation as cis or trans.

c. Translate each structure into a representation with a hexagon for the six-membered ring, and wedges and dashed wedges for groups above and below the ring.

d. Draw the second possible chair conformation for each compound.

Question: a.Draw the three staggered and three eclipsed conformations that result from rotation around the bond labeled in red using Newman projections. b. Label the most stable and least stable conformation.

Question: Convert each of the following structures into its more stable chair form. One structure represents menthol and one represents isomenthol. Menthol, the more stable isomer, is used in lip balms and mouthwash. Which structure corresponds to menthol?

Question: Consider 1,2-dimethylcyclohexane.

  1. Draw structures for the cis and trans isomers using a hexagon for the six-membered ring.
  2. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?
  3. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?
  4. Which isomer, cis or trans, is more stable and why?
See all solutions

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