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 3.5, Problem 6P
The heats of combustion of ethylcyclopropane and methylcyclobutane have been measured as
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Why is the energy difference t-butylcyclohexane (total energy - 13.3019 kcal/mol) significantly greater than the corresponding value methylcyclohexane (total energy - 6.8903 kcal/mol?)
Is cis-1,2-dimethylcyclohexane (total energy - 12.5020 kcal/mol) or trans-1,2-dimethylcyclohexane (total energy - 0.4576 kcal/mol) more stable? Why?
What is(are) the major Organic product(s) in the following reaction?
CH;
CH;
H₂C-C-0-CBr;
CBr;
CH;
H₂C-C-0-CH;
CH;
CB13
Br3C C 0-CH₂
HBr
(SNI)
HC
CH;
H₂C-C-0-H
CH,
(b)
CH;
CH;
Br
CH;Br
CH₂OH
H;C
CH,
H₂C C
|
CH;
CH;
C
CH;
(c)
H
CH
+ CH₂Br
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Rank the following compounds according to their heat of combustion.
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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- Show that the addition of each CH2 unit to an alcohol molecule changes the heat of combustion by: 2(C-H)+1(C-C)+1.5(O=O) – [2(C=O)+2(O-H)]arrow_forwardThe heats of hydrogenation of cycloheptene and 1,3,5-cycloheptatriene are 110 kJ/mol (26.3 kcal/mol) and 305 kJ/mol (73.0 kcal/mol), respectively. In both cases cycloheptane is the product. What is the resonance energy of 1,3,5-cycloheptatriene? How does it compare with the resonance energy of benzene?arrow_forwardEach H↔H eclipsing interaction in ethane costs about 4.0 kJ/mol. How many such interactions are percent in cyclopropane? What fraction of the overall 115 kJ/mol (27.5 kcal/mol) strain energy of cyclopropane is due to torsional strain.arrow_forward
- Gibbs free energy differences between axial-substituted and equatorial-substituted chair conformations of cyclohexane were given in Table 2.4. (a) Calculate the ratio of equatorial to axial tert-butylcyclohexane at 25C. (b) Explain why the conformational equilibria for methyl, ethyl, and isopropyl substituents are comparable but the conformational equilibrium for tert-butylcyclohexane lies considerably farther toward the equatorial conformation.arrow_forwardFollowing are structural formulas and heats of combustion of acetaldehyde and ethylene oxide. Which of these compounds is more stable? Explain.arrow_forwardFollowing are heats of combustion per mole for methane, propane, and 2,2,4-trimeth-ylpentane. Each is a major source of energy. On a gram-for-gram basis, which of these hydrocarbons is the best source of heat energy?arrow_forward
- Draw the skeletal structure of 4- butyl-1,1-dipropylcyclohexane and upload in this material.arrow_forwardWhich compound will produce an irritating bunt fat odor when upon heating together with KHSO4? C,,H3s-C-O Na" HO HO HOarrow_forwardWhich of the followings is the principal organic product of the reaction shown below? TsCl= TSCI CH,CH, pyridine as shown below TS0H CH;CH, as shown below CH;CH, as shown below CH-CH, as shown below T50FOTS CH;CH3 as shown below CH,CH,arrow_forward
- (b) H CH2CH3 ·C. -CH2CH3 CH3 CH3OH (H)arrow_forwardThe heat of combustion of cis-1,2-dimethylcyclopropane is larger than that of the trans isomer. Which isomer is more stable? Use drawings to explain this difference instability.arrow_forwardEach hydrogen-hydrogen eclipsing interaction in ethane costs about 4.0 kJ/mol. How many such interactions are present in cyclopropane? What fraction of the overall 115 kj/mol (27.5 kcal/mol) strain energy of cyclopropane is due to torsional strain?arrow_forward
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