6. Construct a model of methylcyclohexane in the chair form.

Figure n: Axial conformation of Methylcyclohexane

a. Is the methyl group in the axial or equatorial position?
The methyl group is in its axial position.
b. Flip the model to convert it to the other chair conformation. This is done by holding carbons 2, 3, 5 and
6 firmly and flipping carbons 1 and 4.
Two chair forms can be constructed out of methylcyclohexane, with the equatorial one being 1.8
kcal/mol more stable than the other. The axial conformation can be seen in the figure above, while the
equatorial conformation can be seen below:

Figure n: Equatorial conformation of Methylcyclohexane

c. What is the position of the methyl group in the resulting conformation?
The methyl group is in its equatorial position.
d. Considering the positions of the methyl group, which is more stable? axial or equatorial?
Equatorial methyl cyclohexane is more stable; the equatorial conformation is of lower energy than
the axial conformation and as previously stated, the axial methylcyclohexane exhibits steric strain (1.8
kcal/mole), due to the interaction between one hydrogens of the axial methyl group and two other axial
hydrogens. These (gauche) steric interactions, also referred to as 1,3- diaxial interactions, involve 2 axial
groups which are 0.9kcal/mole each (making it 1.8kcal/mole in total) and make the axial conformation of
methylcyclohexane less stable.
7. Construct a model of the different stereoisomers of CH3CHOHCHOHCH3 and draw the Newman
projection.
3 stereoisomers of 2,3-butanediol exist.

Figure n: Levo-butane-2,3-diol (left) and dextro-butane-2,3-diol (right)

Figure n: Meso-butane-2,3-diol

Figure n: Newman projection of butane-2,3-diol

Of these three projections, the first (left-most) in the figure is the most stable because it only has two
Gauche interactions, while the other two have three.
a. Which compounds are enantiomers?
Enantiomers are substances of whose molecular structures are related as an object and its
non-superimposable mirror image (http://www.uncw.edu/chem/courses/chmL211/Summer
%20labs/SS110%20labs/Experiment%2009.pdf). Two stereoisomers of butane-2,3-diol are enantiomers
(levo- and dextro-2,3-butanediol), of which have (2R, 3R) and (2S, 3S) configurations at carbons 2 and 3

Figure n: (R,R)-butane-2,3-diol

Figure n: (S,S)-butane-2,3-diol
b. Which compounds are diasteriomers?
Diasteriomers are isomers which are not enantiomers. The diasteriomer of butane-2,3-diol is meso-2,3butanediol (also seen in Figure n), which has a (2R, 3S) or (2S, 3R) configuration.
References:
Boutron P, (1992). "Cryoprotection of red blood cells by a 2,3-butanediol containing mainly the levo and
dextro isomers". Cryobiology 29(3): 347358
Ege, S. (1997). Answers to Problem Set 4 CHEM 206. Retrieved February 27, 2016 from
http://www.chemistry.mcmaster.ca/~chem2o6/problems/96ans4.html
(n.d). Chapter 4: Stereochemistry. Retrieved February 27, 2016 from
http://www.colby.edu/chemistry/CH241F/Chapter%204.pdf
(n.d). Substituted Cyclohexanes. Retrieved February 27, 2016 from
https://www.chem.umn.edu/groups/taton/chem2301/Handouts/6_27.pdf
(n.d). Stereochemistry: Enantiomers and Diastereomers. Retrieved February 27, 2016 from
http://www.uncw.edu/chem/courses/chmL211/Summer%20labs/SS110%20labs/Experiment%2009.pdf