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Practice Questions-Conformational Analysis

The document contains 16 questions regarding the conformational analysis of organic molecules. Question 1 asks to draw Newman projections and a graph of energy versus rotation for isobutane. Question 4 asks to draw a Newman projection and calculate strain energy for a conformation of 2,3-dimethylbutane. Question 12 asks about the energy difference between axial and equatorial conformations of cyclohexanol.

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Harry Zgambo
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Download as PDF, TXT or read online on Scribd
586 views

Practice Questions-Conformational Analysis

The document contains 16 questions regarding the conformational analysis of organic molecules. Question 1 asks to draw Newman projections and a graph of energy versus rotation for isobutane. Question 4 asks to draw a Newman projection and calculate strain energy for a conformation of 2,3-dimethylbutane. Question 12 asks about the energy difference between axial and equatorial conformations of cyclohexanol.

Uploaded by

Harry Zgambo
Copyright
© © All Rights Reserved
Available Formats
Download as PDF, TXT or read online on Scribd
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UNIVERSITY OF ZAMBIA

CHEMISTRY DEPARTMENT

CHE 2511 BASIC ORGANIC CHEMISTRY


TUTORIAL QUESTIONS-CONFORMATIONAL ANALYSIS 15TH July 2020
Provide solutions to questions 1, 4, 5,7, 9, 12, 14 & 16

QUESTION ONE

Sight along the C2-C1 bond, 2-methylpropane (isobutane) and;

(a) Draw a Newman projection of the most stable conformation.


(b) Draw a Newman projection of the least stable conformation.
(c) Make a graph of energy versus angle of rotation around the C2-C1 bond.
(d) Since an H↔H eclipsing interaction costs 4.0 kJ/mol and an H↔CH3 eclipsing
interaction costs 6.0 kJ/mol, assign relative values to the maxima and minima in your graph.

QUESTION TWO

Make a graph of potential energy versus angle of bond rotation for propane, and assign
values to the energy maxima.

QUESTION THREE

Sight along the C2-C3 bond of 2,3-dimethylbutane, and draw a Newman projection of the
most stable conformation.

QUESTION FOUR

Draw a Newman projection along the C2-C3 bond of the following conformation of
2,3-dimethylbutane, and calculate a total strain energy:

QUESTION FIVE

Consider 2-methylbutane (isopentane). Sighting along the C2–C3 bond:


(a) Draw a Newman projection of the most stable conformation.
(b) Draw a Newman projection of the least stable conformation.
(c) If a CH3↔CH3 eclipsing interaction costs 11 kJ/mol (2.5 kcal/mol) and a CH3↔CH3
gauche interaction costs 3.8 kJ/mol (0.9 kcal/mol), make a quantitative plot of energy versus
rotation about the C2–C3 bond of the molecule?

1
QUESTION SIX

Increased substitution around a bond leads to increased strain. Take the four substituted
butanes listed below, for example. For each compound, sight along the C2–C3 bond and draw
Newman projections of the most stable and least stable conformations. Use the data in Table
to assign strain energy values to each conformation. Which of the eight conformations is
most strained? Which is least strained?
(a) 2-Methylbutane (b) 2,2-Dimethylbutane
(c) 2,3-Dimethylbutane (d) 2,2,3-Trimethylbutane
QUESTION SEVEN

Each H↔H eclipsing interaction in ethane costs about 4.0 kJ/mol. How many such
interactions are present in cyclopropane? What fraction of the overall 115 kJ/mol
(27.5 kcal/mol) strain energy of cyclopropane is due to torsional strain?

QUESTION EIGHT

How many H↔H eclipsing interactions would be present if cyclopentane were


planar? Assuming an energy cost of 4.0 kJ/mol for each eclipsing interaction, how
much torsional strain would planar cyclopentane have? Since the measured total
strain of cyclopentane is 26 kJ/mol, how much of the torsional strain is relieved by
puckering?

QUESTION NINE

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?
QUESTION TEN

Draw two different chair conformations of cyclohexanol (hydroxycyclohexane), showing all


hydrogen atoms. Identify each position as axial or equatorial.

QUESTION ELEVEN
Draw two different chair conformations of trans-1,4-dimethylcyclohexane, and label all
positions as axial or equatorial.
QUESTION TWELVE
What is the energy difference between the axial and equatorial conformations of
cyclohexanol(hydroxycyclohexane)?

QUESTION THIRTEEN

Why do you suppose an axial cyano (–CN) substituent causes practically no 1,3-diaxial steric
strain (0.4 kJ/mol)? Use molecular models to help with your answer.

2
QUESTION FOURTEEN

Draw the more stable chair conformation of the following molecules, and estimate the
amount of strain in each:
(a) trans-1-Chloro-3-methylcyclohexane (b) cis-1-Ethyl-2-methylcyclohexane
(c) cis-1-Bromo-4-ethylcyclohexane (d) cis-1-tert-Butyl-4-ethylcyclohexane

QUESTION FIFTEEN
myo-Inositol, one of the isomers of 1,2,3,4,5,6-hexahydroxycyclohexane, acts as a growth factor in
both animals and microorganisms. Draw the most stable chair conformation of myo-inositol.

QUESTION SIXTEEN
Show by a calculation using the formula G= -RTlnK that a free energy difference of 7.6 kJ
mol-1 between the axial and equatorial forms of methyl cyclohexane at 25 oC (with equatorial
form being more stable) does correlate with an equilibrium mixture in which the
concentration of the equatorial form is approximately 95 %.

3
APPENDIX

Useful Information
TABLE 1.0 ENERGY COST FOR INTERACTIONS IN ALKANE CONFORMERS
ENERGY COST
CAUSE kJ/mol kcal/mol
H –H Eclipsed Torsional Strain 4.0 1.0
H-CH3 Eclipsed Mostly torsional strain 6.0 1.4
CH3-CH3 Eclipsed Torsional strain and steric strain 11 2.6
CH3-CH3 Gauche Steric strain 3.8 0.9

TABLE 2.0 STERIC STRAIN IN MONOSUBSTITUTED CYCLOHEXANES:


1,3-Diaxial strain 1,3-Diaxial strain

Y (kJ/mol) (kcal/mol)
F 0.5 0.12
Cl, Br 1.0 0.5
OH 2.1 0.5
CH3 3.8 0.9
CH2CH3 4.0 0.95
CH(CH3)2 4.6 1.1
C(CH3)3 11.4 2.7
C6H5 6.3 1.5
CO2H 2.9 0.7
CN 0.5 0.1

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