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Question: Draw both conformations for 1-ethyl-1-methylcyclohexane and decide which conformation (if any) is more stable.

Short Answer

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Answer

The following are the conformations of 1-ethyl-1-methylcyclohexane:

Step by step solution

01

Conformational isomers

The stereoisomers that can be easily interconverted into one another by rotating about the carbon-carbon sigma bonds are called conformational isomers.

The interconversion of the conformational isomers can also take place at room temperature.

02

The conformations of 1-ethyl-1-methylcyclohexane

The following structures show the conformational isomers of 1-ethyl-1 methylcyclohexane:

Isomer of 1-ethyl-1-methylcyclohexane

In the above structure, a methyl group (-CH3) is present at the equatorial position, and the ethyl group ( -CH2CH3) is present at the axial position. The above structure is less stable because a bulky ethyl group is present at the axial position.

If present at the axial position, the ethyl group will face 1,3 di axial repulsions, making the structure less stable.

Isomer of 1-ethyl-1-methylcyclohexane

In the above structure, the bulky group, i.e., the ethyl group, is present equatorial. It will face less repulsions from the neighboring groups. As a result, the above structure (II) will be more stable.

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Most popular questions from this chapter

Question: Pristane is a high molecular weight alkane present in shark liver oil, a lipid used as a folk remedy and lubricant by coastal societies in northern Europe for centuries. What is the IUPAC name for pristane?

Pristane

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: a. Using Newman projections, draw all staggered and eclipsed conformations that result from rotation around the bond highlighted in pink in each molecule;

b. draw a graph of energy versus dihedral angle for rotation around this bond.

Question: Consider the tricyclic structure A.

(a) Label each substituent on the rings as axial or equatorial.

(b) Draw a skeletal structure for A, using wedges and dashed wedges to show whether the substituents are located above or below the rings.

A

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?

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