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Chapter 4: Q4-34E (page 114)

Hydrocortisone, a naturally occurring hormone produced in the adrenal glands, is often used to treat inflammation, severe allergies, and numerous other conditions. Is the indicated-OH group axial or equatorial?

Short Answer

Expert verified

The -OHgroup of hydrocortisone indicates the axial position.

Step by step solution

01

Chair form of cyclohexane

Four conformations are possible for cyclohexane: a chair, twist boat, boat, and half chair. Among all the four conformations chair form of cyclohexane is considered a very stable one. Chair conformation of cyclohexane is as follows;

Here 鈥榓鈥� indicates the axial position and 鈥榚鈥� indicates the equatorial position.

02

The -OH group of hydrocortisone

The -OHgroup of hydrocortisone indicates axial position if we compare it with the above chair model of cyclohexane.

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Most popular questions from this chapter

Name the following cycloalkanes:

b. Name the following cycloalkanes:

Two conformations of cis-1,3-dimethylcyclobutane are shown. What is the difference between them, and which do you think is likely to be more stable?

Look at Figure 4-12 on page 105, and estimate the percentages of axial andequatorial conformations present at equilibrium in bromocyclohexane.

Draw the more stable chair conformation of the following molecules, and estimate the amount of strain in each: cis-1-tert-Butyl-4-ethylcyclohexane

One of the two chair structures of cis-1-chloro-3-methylcyclohexane is more stable than the other by 15.5 kJ/mol (3.7 kcal/mol). Which is it? What is the energy cost of a 1,3-diaxial interaction between chlorine and a methyl group?
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