Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 3, Problem 45P
The measured dipole moment of
It may exist entirely in the anti conformation.
It may exist entirely in the gauche conformation.
It may exist as a mixture of anti and gauche conformations.
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Students have asked these similar questions
Draw all three staggered conformations for the following compound, viewed along the C₂-C3 bond. Determine which conformation is
the most stable, taking into account gauche interactions and hydrogen-bonding interactions. (J. Phys. Chem. A 2001, 105, 6991-6997)
Provide a reason for your choice by identifying all of the interactions that led to your decision.
H₂C OH
C₂
HO CH3
Which of the following is the most stable staggered conformer?
Me
Me
***
Conformer B
Me-
Me
Conformer A
Me
Conformer C
Me
Conformer B because the anti OH groups avoid hydrogen bonding, which is a destabilizing effect.
Conformer A because there are only two gauche interactions, and hydrogen bonding between the two OH groups is a
stabilizing effect.
Conformer C because there is no steric strain for Me-OH gauche interactions and hydrogen bonding between the two OH
groups is a stabilizing effect.
Conformer B because the large OH groups are anti to each other.
From studies of the dipole moment of 1,2-dichloroethane in the gas phase at room temperature (25°C), it is estimated that the ratio of molecules in the anti conformation to gauche conformation is 7.6 to 1. Calculate the difference in Gibbs free energy between these two conformations.
C6H12
From the chair conformation, rotate about the carbon-carbon bonds of the ring to form a boat conformation. In the boat conformation carbon atoms 1 and 4 are both above (they could also both be below) the plane described by carbon atoms 2, 3, 5 and 6. Look through each of the C-C bonds in the cyclohexane ring. Do you observe any eclipsing interactions? If so, describe what atoms/substituents are eclipsing.
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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- Consider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energyarrow_forwardmyo-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.arrow_forwardFollowing is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4. (b) Which of these hydrogens are equatorial? Which are axial? (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?arrow_forward
- The anti-conformation is the most stable n-butane conformation. If you could take a snapshot of a mole of n-butane, would a sizeable number of the molecules be in the gauche-conformation? Why or why not?arrow_forwardWhich conformation is the most STABLE STAGGERED conformation of 2,3-dimethylbutane along the C2-C3 bond?arrow_forwardConsider a Newman Projection for 2,2,3-trimethylbutane. Which of the following is true? The least stable conformation of the molecule has 22 kJ/mol of straih energy. The least stable conformation has 28 kJ/mol of torsional strain energy. The most stable conformation of the molecule has two gauche butane interactions with 7.6 kJ/mol of strain energy. The most stable conformation of the molecule has no torsional strain interactions. O O O Oarrow_forward
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