ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 7.6, Problem 14P
Write structural formulas for the six isomeric
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Two alkenes undergo hydrogenation to yield a mixture or cis- and trans-1,4-dimethylcyclohexane. Which two are these? A third, however, gives only cis-1,4-dimethylcyclohexane. What compound is this?
The heat of hydrogenation of cis-2,2,5,5-tetramethyl-3-hexene is -154 kJ (-36.7 kcal)/ mol, while that of the trans isomer is only -113 kJ (-26.9 kcal)/mol.
Q.) Why is the heat of hydrogenation of the cis isomer so much larger (more negative) than that of the trans isomer?
How many different Alkenes with the molecular formula C7H14 will produce 2,4 dimethyl pentane upon hydrogenation. Draw them below
Chapter 7 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
Ch. 7.1 - Name each of the following using IUPAC...Ch. 7.1 - Prob. 2PCh. 7.2 - How many carbon atoms are sp2-hybridized in the...Ch. 7.3 - Prob. 4PCh. 7.3 - Are cis-2-hexene and trans-3-hexene stereoisomers?...Ch. 7.4 - Prob. 6PCh. 7.4 - Prob. 7PCh. 7.4 - Give the IUPAC name of each of the compounds in...Ch. 7.5 - Arrange the following in order of increasing...Ch. 7.6 - Prob. 10P
Ch. 7.6 - Standard enthalpies of formation are known for all...Ch. 7.6 - Prob. 12PCh. 7.6 - Despite numerous attempts, the alkene...Ch. 7.6 - Write structural formulas for the six isomeric...Ch. 7.7 - Place a double bond in the carbon skeleton shown...Ch. 7.9 - Identify the alkene obtained on dehydration of...Ch. 7.10 - Prob. 17PCh. 7.11 - Prob. 18PCh. 7.12 - Prob. 19PCh. 7.13 - The alkene mixture obtained on dehydration of...Ch. 7.14 - Write the structures of all the alkenes that can...Ch. 7.14 - Write structural formulas for all the alkenes that...Ch. 7.15 - A study of the hydrolysis behavior of...Ch. 7.15 - Use curved arrows to illustrate the electron flow...Ch. 7.15 - Predict the major product of the reaction shown.Ch. 7.16 - Prob. 26PCh. 7.17 - Prob. 27PCh. 7.18 - Prob. 28PCh. 7.19 - Predict the major organic product of each of the...Ch. 7.19 - A standard method for the synthesis of ethers is...Ch. 7 - Write structural formulas for each of the...Ch. 7 - Prob. 32PCh. 7 - Give an IUPAC name for each of the following...Ch. 7 - A hydrocarbon isolated from fish oil and from...Ch. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - Choose the more stable alkene in each of the...Ch. 7 - Suggest an explanation for the fact that...Ch. 7 - Prob. 41PCh. 7 - Write structural formulas for all the alkene...Ch. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Predict the major organic product of each of the...Ch. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - The rate of the reaction In the first order in...Ch. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - You have available 2,2-dimethylcyclopentanol (A)...Ch. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Acid-catalyzed dehydration of...Ch. 7 - The ratio of elimination to substitution is...Ch. 7 - Prob. 57PCh. 7 - Prob. 58DSPCh. 7 - Prob. 59DSPCh. 7 - Prob. 60DSPCh. 7 - Prob. 61DSPCh. 7 - A Mechanistic Preview of Addition Reactions The...Ch. 7 - Prob. 63DSPCh. 7 - Prob. 64DSPCh. 7 - Prob. 65DSP
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- Which will be more stable, cis or trans-1,4-tert-butylcyclohexane? Explain by drawing their structures?arrow_forwardFollowing are structural formulas and heats of combustion of acetaldehyde and ethylene oxide. Which of these compounds is more stable? Explain.arrow_forwardDraw a structural formula for the most stable carbocation with each molecular formula. Q.) C3H7O+arrow_forward
- Order the compounds below from least to most thermodynamically stable (relative to their constituent elements) at 25oC. name formula △Gof(kJmol) dichloromethane CH2Cl2(l) -63.2 hydrazine N2H4(l) +149.4 hydrogen peroxide H2O2(l) -120.4 (least stable) < < (most stable)arrow_forwardThe heat of hydrogenation of cis-2,2,5,5-tetramethyl-3-hexene is -154 kJ (-36.7 kcal)/ mol, while that of the trans isomer is only -113 kJ (-26.9 kcal)/mol. Q.) If a catalyst could be found that allowed equilibration of the cis and trans isomers at room temperature (such catalysts do exist), what would be the ratio of trans to cis isomers?arrow_forwardWhich would you predict to have the larger (more negative) heat of combustion, cis-1,4-dimethylcyclohexane or trans-1,4-dimethylcyclohexane?arrow_forward
- The heat of combustion of decahydronaphthalene (C10H18) is -6286 kJ/mol. The heat of combustion of naphthalene 1C10H82 is -5157 kJ/mol. (In both cases CO2(g) and H2O(l) are the products). Calculate the heat of hydrogenation and the resonance energy of naphthalene.arrow_forwardWhen two six-membered rings share a C—C bond, this bicyclic system is called a decalin. There are two possible arrangements: trans-decalin having two hydrogen atoms at the ring fusion on opposite sides of the rings, and cis-decalin having the two hydrogens at the ring fusion on thesame side.a.Draw trans- and cis-decalin using the chair form for the cyclohexane rings. b.The trans isomer is more stable. Explain why.arrow_forwardReaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis-and trans-1-bromo-3-methylcyclohexane and cis-and trans-1-bromo-2-methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1, 2-dibromocyclohexane as the soleproduct. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.arrow_forward
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