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Chapter 4: Q.18. (page 128)

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

Short Answer

Expert verified

Answer

The increasing order of the energy isD<A<B<C .

Step by step solution

01

Staggered and eclipsed conformation

The energy of a conformation is based on its structure. Energy is based on the stability or repulsion of the groups. The conformation that is stable has less energy as compared to the unstable conformation.

02

Explanation for the order of energy

Compounds A and D are staggered conformation. The energy of staggered conformation is less than the eclipsed conformation as there would be less repulsion between the bulky groups.

Compound D is more stable than compound A as it has less repulsion between the bulkier groups. The energy of compound D is the least. Thus, the order is D<A .

Compounds B and C have eclipsed conformation. There would be more repulsion between the bulkier groups (methyl-ethyl) in compound C compared to compound B (ethyl -hydrogen). Thus, the energy of compound B is less than that of C.

The increasing order of energy is mentioned below:

D<A<B<C

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Most popular questions from this chapter

Question: Answer the following questions about compound A, which contains a -CH3group and OH group bonded to the carbon skeleton that consists of three six-membered rings in the conformation shown.

a. Are the -CH3and OH groups oriented cis or trans to each other?

b. Is a substituent on localid="1648626189057" Cathat is cis to the CH3 group located in the axial or equatorial position?

c. Is an equatorial Br at Cboriented cis or trans to the OH group?

d. Is the H atom on Cclocated cis or trans to the OH group?

e. Is a substituent on Cdthat is trans to the OH group located in the axial or equatorial position?

Question: Draw the three constitutional isomers having molecular formula C7H14that contain a five-membered ring and two methyl groups as substituents. For each constitutional isomer that can have cis and trans isomers, draw the two stereoisomers.

Draw the staggered and eclipsed conformations that result from rotation around the C-C bond inCH3-CH2Br.

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: a. Which compounds (B–F) are identical to A? b. Which compounds (B–F) represent an isomer of A?
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