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Chapter 4: Q.20. (page 128)

Question: Calculate the destabilization present in each eclipsed conformation.

a.

b.

Short Answer

Expert verified

Answer

a. The destabilization energyis 3.8 kcal/mol.

b. The destabilization energy is 4.2 kcal/mol.

Step by step solution

01

Conformation

The two main types of conformations are:

  • eclipsed and
  • staggered.

These are based on the dihedral angle.

The conformations are shown below:

Eclipsed and Staggered

02

Calculation of the destabilization energy of a

a. There is one H, H and two CH3, H eclipsing interactions in the given conformation. The value of the destabilization energyis calculated as follows:

role="math" localid="1648531767188" 鈭�E=1H,Heclipsing+2CH3,Heclipsing=1脳1.0+2脳1.4kcal/mol=3.8kcal/mol

Thus, the destabilization energy is 3.8 kcal/mol.

03

Calculation of the destabilization energy of b

b. There are three CH3, H eclipsing interactions in the given conformation. The value of the destabilization energy is calculated as follows:

鈭�E=3CH3,Heclipsing=3脳1.4kcal/mol=4.2kcal/mol

Thus, the destabilization energy is 4.2 kcal/mol.

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Most popular questions from this chapter

Question: Draw the products of combustion of each alkane.

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Question: Consider rotation around the carbon-carbon bond in 1,2-dichloroethane (ClCH2CH2Cl).

a.Using Newman projections, draw all of the staggered and eclipsed conformations that result from rotation around this bond.

b. Graph energy versus dihedral angle for rotation around this bond.

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?

Question: Rank the following conformations in order of increasing energy.

Question: When two six-membered rings share a C-C bond, this bicyclic system is called decalin. There are two possible arrangements: trans-decalin having two hydrogen atoms at the ring fusion on opposite sides of the rings, and cis-decalin having the two hydrogens at the ring fusion on the same side.

  1. Draw trans- and cis-decalin using the chair form for the cyclohexane rings.
  2. The trans isomer is more stable. Explain why.
See all solutions

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