Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 3, Problem 41P
One stereoisomer of
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The barrier of rotation for the C–C bond in bromoethane is 3.7 kcal/mol. We previously learned that an eclipsing C–H bond with another C–H is about 1 kcal/mol each. Based on this, what is the energy cost to eclipse a C–H bond with a C–Br bond?
Stereoisomers 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
trans-1,4-dibromocyclohexane
cis-1,2-dimethylcyclobutane
cis-1,3-dimethylcyclobutane
On a cyclohexane ring, an axial carboxyl group has a conformational energy of 5.9 kJ (1.4 kcal)/mol relative to an equatorial carboxyl group. Consider the equilibrium for the alternative chair conformations of trans-1,4-cyclohexanedicarboxylic acid. Draw the less stable chair conformation on the left of the equilibrium arrows and the more stable chair on the right. Calculate DG0 for the equilibrium as written and calculate the ratio of the more stable chair to the less stable chair at 25°C.
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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- Both 1,2-dihydronaphthalene and 1,4-dihydronaphthalene may be selectively hydrogenated to 1,2,3,4-tetrahydronaphthalene.One of these isomers has a heat of hydrogenation of 101 kJ/mol (24.1 kcal/mol), and the heat of hydrogenation of the other is 113 kJ/mol (27.1 kcal/mol). Match the heat of hydrogenation with the appropriate dihydronaphthalene.arrow_forwardOnly three stereoisomers are possible for 2,3-dibromo-2, 3-dichlorobutane. Draw them, indicating which pair are enantiomers (optical isomers). Why does the other isomer not have an enantiomer?arrow_forwardDefine the three stereoisomers of 2,3-dibromobutane?arrow_forward
- How many possible stereoisomers can be written for 1-ethyl-3- methylcyclohexane? O 2 O4 8arrow_forwardIs cis-1,3-dimethylcyclohexane (total energy - 12.5020 kcal/mol) or trans-1,3-dimethylcyclohexane (total energy - 9.0056 kcal/mol) more stable? Why? Is cis-1,2-dimethylcyclohexane (total energy - 12.5020 kcal/mol) conformational isomer of trans-1,2-dimethylcyclohexane (total energy - 9.0056 kcal/mol) ? Explain your reasoning.arrow_forwardDraw the optically active stereoisomer(s) of 1,3-dimethoxycyclohexane.arrow_forward
- Name and draw structural formulas for the eight constitutional isomeric alcohols with molecular formula C5H12O. Classify each alcohol as primary, secondary, or tertiary. Which are chiral?arrow_forwardDraw structural formulas for the cis and trans isomers of hydrindane. Show each ring in its most stable conformation. Which of these isomers is more stable?arrow_forwardDraw the most stable conformers of trans-1-Bromo-4-methylcyclohexane and cis-1-Bromo-4-methylcyclohexane. Which is more stable? Explain the reason for your answer.arrow_forward
- Draw the structures of the two chair conformations of trans-1-tert-butyl-4-ethylcyclohexane. Which conformation is more stable? Explain your answer.arrow_forwardExplain the four stereoisomers of 2,3-dibromopentane ?arrow_forwardWhen cyclohexane is substituted by an ethynyl group, -C=CH, the energy difference between axial and equatorial conformations is only 1.7 kJ (0.41 kcal)/mol. Compare the conformational equilibrium for methylcyclohexane with that for ethynylcyclohexane and account for the difference between the two.arrow_forward
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