ORGANIC CHEMISTRY,VOL.1 >CUSTOM<
10th Edition
ISBN: 9781260020724
Author: Carey
Publisher: MCG CUSTOM
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Chapter 3.5, Problem 6P
The heats of combustion of ethylcyclopropane and methylcyclobutane have been measured as
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The 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.
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True or False:
1. The eclipsed conformation of a linear alkane IS called cis, while the anti conformation of an alkane IS called trans.
2. In the conversion of open-chain D-glucose to the ring form, the aldehyde carbon (carbon #1) bonds to the oxygen on carbon number 5 to form a ring that is both PYRANOSE and UNLOCKED.
Chapter 3 Solutions
ORGANIC CHEMISTRY,VOL.1 >CUSTOM<
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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- The same alkane is obtained from the catalytic hydrogenation of both alkene A and alkene B. The heat of hydrogenation of alkene A is 29.8 kcal/mol, and the heat of hydrogenation of alkene B is 31.4 kcal/mol. Which alkene is more stable?arrow_forwardAs we learned, monosubstituted cyclohexanes exist as anequilibrium mixture of two conformations having either an axial orequatorial substituent. When R = CH2CH3, Keq for this process is 23.When R = C(CH3)3, Keq for this process is 4000. Question: a.) When R = CH2CH3, which conformation is present in higherconcentration?b.) Which R shows the higher percentage of equatorial conformation atequilibrium?arrow_forwardGibbs 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_forward
- Following 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_forwardIn the conversion of open-chain D-glucose to the ring form, the aldehyde carbon (carbon #1) bonds to the oxygen on carbon number 5 to form a ring that is both PYRANOSE and UNLOCKED. Group of answer choices True or false?arrow_forwardThe G° for conversion of “axial” fluorocyclohexane to “equatorial” fluorocyclohexane at 25 °C is -0.25 kcal>mol. Calculate the percentage of fluorocyclohexane molecules that have the fluoro substituent in an equatorial position at equilibrium.arrow_forward
- Table 6.4. Oxidation: Reaction with Baeyer’s reagent (cold, dilute, neutral, aqueous KMnO4) Write (+) if the reaction is positive, (-) if negative. SAMPLE OBSERVATIONS +/- cyclohexane cyclohexene benzene toluene acetylene Enumerate the classes of hydrocarbons that are oxidizable by Baeyer’s reagent. ________________________________________________________________________ ________________________________________________________________________ What is the structural feature of these classes of hydrocarbons? ________________________________________________________________________ ________________________________________________________________________arrow_forwardTert-butylcyclohexane exists practically (> 99.99%) in a single conformational form. Represent in perspective the most stable conformer of trans-4 isopropylcyclohexan-1-ol.arrow_forwardPlease write the answer clearly with the state of matter following each compound.arrow_forward
- Rank the following groups in order of decreasing priority. −H, −CH3, −Cl, −CH2Clarrow_forwardDHA is a fatty acid derived from sh oil and an abundant fatty acid in vertebrate brains. Hydrogenation of DHA forms docosanoic acid [CH3(CH2)20CO2H] and ozonolysis forms CH3CH2CHO, CH2(CHO)2 (ve equivalents), and HCOCH2CH2CO2H. What is the structure of DHA if all double bonds have the Z conguration?arrow_forwardRank the conformations of n-butane with reference to its potential energy from the most stable to the least stable. Rank from the most stable to the least stable.To rank items as equivalent, overlap them.arrow_forward
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