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 3.2, Problem 3P
Sketch a potential energy diagram for rotation around a carbon–carbon bond in propane.
Identify each potential energy maximum and minimum with a structural formula that shows the conformation of propane at that point. Does your diagram more closely resemble that of ethaneor of butane? Would you expect the activation energy for bond rotation in propane tobe morethan or less than that of ethane? Of butane?
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Compare the relative conformational energydiagrams of ethane and propane.
Define Cyclopropanation ?
One of the chair conformations of cis-1-chloro-3-methylcyclohexane is more stable than the other by 15.5 kJ/mol. Use this, and the table below, to estimate the energy cost of a 1,3-diaxial
interaction between a chlorine atom and a methyl group.
1,3-Diaxial Strain Energies for Monosubstituted
Cyclohexanes
kJ/mol
Substituent
Substituent kJ/mol
-NH2
-CN, cyano
0.4
2.95
-F
0.5
-COOH
2.95
-C=CH, ethynyl 0.85
-CH=CH2
3.55
-CH3
-I
0.95
3.64
-CH2CH3
-Cl
3.65
1.1
-CH(CH3)2
1.2
4.5
-Br
-C(CH3)3
10.5
-ОН
1.95
-CGH5
6.3
(Round your answer to one decimal place.)
kJ/mol
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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- It is easy to imagine a cyclohexane as a flat hexagon and a lot of the time we draw it that way. Looking at 1,3,5-triethylcyclohexane we cannot tell the stability of the molecule from looking at the flat 2D drawing. Explain why we need to look at the 3D configuration and what conformation (axial,equatorial) would each of the three ethyl groups be in for the most stable configuration.arrow_forwardStereoisomers share the same connectivity and differ only in the way their atoms are arranged in space. Draw the structure of a compound that is a stereoisomer of cis-1,2- dibromocyclobutane. (Note that the question asks for a different stereoisomer of the named compound and not the named compound itself.) • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • In cases where there is more than one answer, just draw one.arrow_forwardWrite a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.arrow_forward
- Describe the most stable conformation of each ring and compare these conformations with the chair conformation of cyclohexane.arrow_forwardWhat is the most stable conformation for trans-1,2-dichlorocyclohexane. Describe and explain brieflyarrow_forwardIs there a difference in the stability of the two cyclohexane conformations?arrow_forward
- Draw a structural formula and Draw the structure of a compound that is a stereoisomerarrow_forwardWhich of the following compounds contain stereocenters? Also, what are stereocenters?arrow_forwardDescribe the conformations of the following: E) Gauche conformation of ethane, (ü) felipsed conformation of ethene, (iii) Staggered conformation of propane, (iv) Syn- and anti-conformation of butane.arrow_forward
- The structure of a trisubstituted cyclohexane is shown, but no information is given about whether the groups are "up" or "down": that is, wedge and dash notation has not been used. Change the exo-cyclic bonds to represent the structure that will have the most stable chair conformation.arrow_forwardFollowing are structural formulas for 1,4-dioxane and piperidine. 1,4-Dioxane is a widely used solvent for organic compounds. Piperidine is found in small amounts in black pepper (Piper nigrum). (a) Complete the Lewis structure of each compound by showing all unshared electron pairs. (b) Predict bond angles about each carbon, oxygen, and nitrogen atom. (c) Describe the most stable conformation of each ring and compare these conformations with the chair conformation of cyclohexane.arrow_forwardFollowing is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this compound and state which of the two is more stable.arrow_forward
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