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Chapter 3: Q51 (page 190)

Question: The most stable form of 1,2,3,4,5,6-Cyclohexanehexolcontains a six-membered ring in the chair conformation with all the substituents equatorial. Draw this most stable conformation of cyclohexanehexol

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01

Chair conformation

Chair conformation is the most stable conformation of cyclohexane, with one part puckered upward and another part puckered downward.

02

Axial and equatorial positions of cyclohexane

Axial bonds are directed vertically parallel to the axis of the ring, and the equatorial bonds are directed outward from the equator of the ring. As the carbon atoms are numbered in cyclohexane, it can be seen that the odd-numbered carbons have their upward bonds in the axial position and their downward bonds in an equatorial position. The even-numbered carbons have their downward bonds in the axial position and their upward bonds in an equatorial position.

03

Drawing the most stable conformation of 1,2,3,4,5,6-Cyclohexanehexol

All the groups in the most stable conformation are in an equatorial position.

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Most popular questions from this chapter

Draw a perspective representation of the most stable conformation of 3-methylhexane.

Name the following compounds. Remember the two up bonds are cis; two down bonds are cis; one up and one down bond are trans.

Construct a graph, similar to Figure 3-11, of the torsional energy of 3-methylpentanealong theC2−C3.PlaceC2in front, represented by three bonds coming together in a Y shape, andC3in back, represented by a circle with three bonds pointing out from it. Define the dihedral angle as the angle between the methyl group on the front carbon and ethyl group on the back carbon. Begin your graph at 00thedihedral angle and begin to turn the front carbon. Show the Newman projection and the approximate energy at each600of rotation. Indicate which conformations are the most stable (lowest energy) and the least stable (highest energy).

Question: Using the general formula for alkanes

  1. Predict the molecular formula of theC27straight chain alkane.
  2. Predict the molecular formula of the alkanes containing 42 carbon atom with extensive branching.

Draw 1,2,3,4,5,6-hexamethylcyclohexane with all the methyl groups

(a) in axial positions. (b) in equatorial positions.
See all solutions

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