Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Question
Chapter 3.2, Problem 5P
Interpretation Introduction
Interpretation:
The activation energy for the rotation about the
Concept introduction:
In case of butane, the anti conformation has the least energy while the eclipsed conformation has the highest energy.
The rotation of the bond due to which different conformations arise requires gain of energy.
The gauche and anti conformers have only a slight difference in energy, but their interconversion occurs through an intermediate eclipsed conformation.
This requires energy equal to the activation energy.
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Estimate the strain energy of the following 2,3-dimethylbutane conformation.
Use strain energy increments from the table given in the question, and be sure to specify your units, e.g.kJ/mol. Calculate energy to the nearest 0.1 energy unit.
Strain Energy Increments
strain
CH3
Ø
CH3
H.
H
CH3
The strain energy is
Interaction
HH eclipsing
H→ CH3 eclipsing
CH3 CH3 eclipsing
CH3 CH3 gauche
→
→
kJ/mol kcal/mol
4.0
6.0
11.0
3.8
1.0
1.4
2.6
0.9
Draw a structural formula for the one constitutional isomer of the
unbranched alkane C7H16 in which the longest carbon chain has 4
atoms.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• In cases where there is more than one answer, just draw
one.
ST12A.1 - Determine the temperature [in K] at which the relative proportion of molecules in axial and equatorial conformations in a sample of methylcyclohexane is 0.207. Note
that we are talking about a ratio A:E rather than a typical percentage A/(A+E). The axial conformation is 6.0 kJ/mol higher than the equatorial configuration.
Type your answer...
Chapter 3 Solutions
Organic Chemistry - Standalone book
Ch. 3.1 - Identify the alkanes corresponding to each of the...Ch. 3.1 - Find the conformations in Figure 3.4 in which the...Ch. 3.2 - Sketch a potential energy diagram for rotation...Ch. 3.2 - Acetylcholine is a neurotransmitter in the central...Ch. 3.2 - Prob. 5PCh. 3.5 - The heats of combustion of ethylcyclopropane and...Ch. 3.8 - Prob. 7PCh. 3.10 - The following questions relate to a cyclohexane...Ch. 3.10 - Draw the most stable conformation of...Ch. 3.11 - Prob. 10P
Ch. 3.11 - Prob. 11PCh. 3.12 - Based on what you know about disubstituted...Ch. 3.12 - Write structural formulas for the most stable...Ch. 3.14 - Cubane (C4H8) is the common name of the polycyclic...Ch. 3.14 - Prob. 15PCh. 3.14 - Prob. 16PCh. 3.14 - Prob. 17PCh. 3.14 - Prob. 18PCh. 3.15 - Prob. 19PCh. 3 - Give the IUPAC names of each of the following: (a)...Ch. 3 - Draw Newman projections for the gauche and...Ch. 3 - Identify all atoms that are (a) anti and (b)...Ch. 3 - Prob. 23PCh. 3 - Prob. 24PCh. 3 - Prob. 25PCh. 3 - Prob. 26PCh. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Oxidation of 4-tert-butylthiane proceeds according...Ch. 3 - The following are representations of two forms of...Ch. 3 - Draw (a) a Newman projection of the most stable...Ch. 3 - Write a structural formula for the most stable...Ch. 3 - Sight down the C-2-C-3 bond, and draw Newman...Ch. 3 - Prob. 34PCh. 3 - Sketch an approximate potential energy diagram for...Ch. 3 - Prob. 36PCh. 3 - Even though the methyl group occupies an...Ch. 3 - Which do you expect to be the more stable...Ch. 3 - Arrange the trimethylcyclohexane isomers shown in...Ch. 3 - Identify the more stable stereoisomer in each of...Ch. 3 - One stereoisomer of 1,1,3,5-tetramethylcyclohexane...Ch. 3 - One of the following two stereoisomers is...Ch. 3 - In each of the following groups of compounds,...Ch. 3 - The heats of combustion of the more and less...Ch. 3 - The measured dipole moment of ClCH2CH2Cl is 1.12D....Ch. 3 - Prob. 46PCh. 3 - Prob. 47PCh. 3 - Prob. 48DSPCh. 3 - Prob. 49DSPCh. 3 - Prob. 50DSPCh. 3 - Prob. 51DSPCh. 3 - Prob. 52DSPCh. 3 - Prob. 53DSP
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