Alkane Stereochemistry 1) For the molecules below: a) Provide a 3 dimensional structure at the indicated atoms. b) Draw the Newman projection for your...
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Alkane Stereochemistry 1) For the molecules below: a) Provide a 3 dimensional structure at the indicated atoms. b) Draw the Newman projection for your structure indicating the direction of sight with an arrow. c) Draw the Newman projection for the most stable conformation. d) Draw the Newman projection for the least stable conformation. e) If possible, calculate the energy difference between the most and least stable conformations. (H3C)2HC
H3C H3CH
Most Stable
H H3C
CH3
(H3C)2HC
HH
H3C
H
H3CH
CH3 H
H
H
H3C
H
H3C 6 kJ/mol H Least Stable
HH 4 kJ/mol
H H3C 6 kJ/mol
H3CH2C CH2OH barrier to rotation = 17kJ/mol (why?)
CH2CH3
HH
HH
CH3 H
H
H CH3
H
H3C 11 kJ/mol CH3 H H3C 6 kJ/mol
HH
H3C
CH3
H3CH2C
H3C
CH3 H
:
H
H
OH
H3C OH
HH 4 kJ/mol
CH3
H
:
H
H3C H HH 4 kJ/mol
H H
O H
HH
OH
OH
H
:
:H
4 kJ/mol 17 - 4 - 4 = 9 kJ/mol for each CH3 : OH eclipse
2) a) b) c) d)
Draw a chair cyclohexane and put in all the axial bonds. On a second chair cyclohexane, put in all the equatorial bonds. Draw a cyclohexane with a bromine in an equatorial position. Draw a cyclohexane with a bromine in an axial position. (a)
(b)
(c)
(d)
Br
Br equatorial bonds
axial bonds
3) Draw both possible conformations for the indicated cyclohexane: a) trans-1-chloro-2-methylcyclohexane. e) trans-1-chloro-4-methylcyclohexane. b) cis-1-chloro-2-methylcyclohexane. f) cis-1-chloro-4-methylcyclohexane. c) trans-1-chloro-3-methylcyclohexane. g) a cyclohexane with 2 methyl groups, both axial. d) cis-1-chloro-3-methylcyclohexane. h) a cyclohexane with 2 methyl groups, both equatorial. a
Cl
b
Cl
c
Cl
Cl Cl
Cl
e
d
f
Cl
Cl
Cl Cl
Cl
Cl
g
h one possible answer
one possible answer
4) Draw the Newman projection for 3 a-d. (a)
H
Cl
H
H
H
H CH3
H
H
Cl
H
H
H H
(c)
H H3C
H
H
H
H
H
H
H
H
H
H
CH3
H
Cl
(b)
H
CH3
Cl
H
(d)
H
H
H
H
Cl
H
H
CH3
Cl
H
H
CH3
H
H
H
H
H3C
H
H
H
CH3 Cl
H
H
H
H
H
H
H
Cl H
5) For the following pairs: a) Circle the more stable cyclohexane. b) Calculate the energy difference between the two structures, if possible. see McMurry Fig. 4.22 c) Indicate whether the structures are conformers (conformational isomers) or stereoisomers. (b)
(a)
CH *CH *
3
t
Cl
3
*
Bu
CH3
H3C
Me
conformers,
Me * Bu Cl* 13.6 kJ/mol t
conformers, 23 kJ/mol (see problem 4.44) (c)
*
NC
Et Et
(e)
* H
H
Me H
H H
7.2 kJ/mol
CN
*
H CO2H
(d)
CN CN
conformers 8.8 kJ/mol
*Et 8.0 kJ/mol
Et
*
0.8 kJ/mol conformers, 7.2 kJ/mol
Me H
H H
H
H H CO2H
* 5.8 kJ/mol
conformers, 1.8kJ/mol
(f)
Cl
* t
t
Bu
Me
*
Cl
Me
Bu
*
9.2 7.2 stereoisomers, 2 kJ/mol
6) For every structure above, star the axial substituents and box the equatorial substituents.
7) For every structure below, draw the most stable chair conformation. Where two or more conformations are equally stable, draw both. Cl Br
