McMurry (Kap.4,6)

Question 1

What does the substituents on the cyclohexane get influenced by?

Answer 1

The chair conformation influences the chemistry/chemical behavior of the substituents.

The same goes for the twist boat conformation

Question 2

What two positions can the substituents undertake when in chair conformation?

Answer 2

The equatorial position
The axial position

Question 3

Describe the axial position, and the equatorial position

Answer 3

The six axial positions are perpendicular (vinkelret) to the ring/parallel to the ring axis.

The six equatorial positions are around the ring axis.

Question 4

How many equatorial and axial positions can each carbon have in the cyclohexane?

Answer 4

One axial and one equatorial.

each face of the ring (side) has three axial and three equatorial alternating.

Question 5

Is the equatorial and axial positions trans or cis steriopositioned?

Answer 5

It does not matter if two substituents are equatorial or axial positioned, they can still have the CIS-steriochemistry.

The thing that matters is if the substituents are on the same face(side) of the ring or on the opposite sides of the ring.

Same side of the ring (whether axial or equatorial) = CIS.

Opposite side of the ring (whether axial or equatorial) = TRANS

Question 6

How can axial and equatorial positions be drawn in the cyclohexane?

Answer 6

See the tutorial on page 100.

Question 7

Do you typically find one form of chair conformer where only the equatorial or the axial position is in use?

Answer 7

No, these two interchange so quickly between each other (because cyclohexane is conformationally mobile at room temperature), therefore these two positions happens so quickly that both exist.

Question 8

What is it named when the interchange happen between axial and equatorial position in the molecule?

Answer 8

Called a RING FLIP.

Question 9

How do you draw a ring flip

Answer 9

See Page 101 for tutorial