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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 1E

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Question

100%

Consider a Newman projection of 2-methylbutane shown. Calculate
the energy from the strain present in this conformation.
CH3
CH3
kcal/mol
H.
1
H
CH3
6
Strain Enery
kcalmo
Interaction Type
guche H
guche CCH,
cosed CH,
cioned C C,
07
7
8
9
33
+/-
x 100
3.
2.
4.

The general values for steric and torsional strain are provided. Use
these values to calculate the amount of strain in the molecule in the
box.
kJ/mol
1
3
H ond
4m toronan
6
C ond
SAma
CHyCH, d
11ma n
7
8
9.
+/-
х 100
2.
5.
4.

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Consider the molecule 1-bromo-2-methylbutane. C3 and C4 should be drawn as Et as in theexample. This group is called an ethyl group and can be considered a sphere about twice the sizeof a methyl group. Draw the following Newman projections sighting down the C1C2 bond... a. The lowest potential energy conformation. b. The highest potential energy staggered conformation.
The highest energy conformation of ethane has 12 kJ/mol of strain. The two highest conformations of butane have 16 and 19 kJ/mol of strain, respectively. How much strain does the highest energy conformation of 2,3-dimethylbutane have?
Amongst the given Newmann projections, identify the Newmann projection corresponding to most stable conformation of 2-methylpentane.
The potential energy of a CH3 group in ethane as it is rotated around the C-C bond can be written V= 1/2V0(1 +cos φ), where φ is the azimuthal angle as shown and V0 = 11.6 kJ mol-1. (a) What is the change in potential energy between the trans and fully eclipsed conformations? (b) Show that for smal lvariations in angle, the torsional (twisting) motion around the C-C bond can be expected to be that of a harmonic oscillator. (d) Estimate the vibrational frequency of this torsional oscil lation.
Consider 1-bromo-2-methylpropane and draw the following. Q) The staggered conformation(s) of lowest energy
Consider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?
For the 1,2-dichlorocyclohexane stereoisomers, which conformation of the trans stereoisomer has the lower energy, the diaxial or the diequatorial conformer? Which isomer and conformation of the three you built has the lowest energy? E of all the isomers of 1,2-dichlorocyclohexane. Explain the differences in energy, i.e., identify the sources of strain in the conformations you built. Show the sources of strain in a drawing.
Draw the most stable conformation of the molecule while taking into account the approximate values of the energies of the following skew interactions:
Can someone tell me what the appropiate E/Z conformation for this example is?
Consider 1-bromo-2-methylpropane and draw the following. Q) The staggered conformation(s) of highest energy
Give the most stable conformation for (1S, 2S)-1-methoxy-2-chlorocyclohexane.
Which chair conformation of cis- and trans-1,4-dimethylcyclohexane has the lowest potenital energy? Which is the most stabel? Why?

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