Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Chapter 5.9, Problem 26P
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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?
The 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?
a. What alkane, with molecular formula C5H12, forms only one monochlorinated product when it is heated with Cl2?
b. What alkane, with molecular formula C7H16, forms seven monochlorinated products (disregarding stereoisomers) when heated with Cl2?
Chapter 5 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 5.1 - What is the molecular formula for each of the...Ch. 5.1 - Prob. 4PCh. 5.1 - Determine the degree of unsaturation and then draw...Ch. 5.1 - Prob. 6PCh. 5.2 - What is each compounds systematic name?Ch. 5.2 - Prob. 8PCh. 5.2 - Draw the structure for each of the following: a....Ch. 5.3 - How many carbons are in the planar double-bond...Ch. 5.3 - Prob. 12PCh. 5.5 - Prob. 13P
Ch. 5.5 - Prob. 14PCh. 5.5 - Prob. 16PCh. 5.5 - Prob. 17PCh. 5.6 - a. Which of the monosubstituted cyclohexanes in...Ch. 5.6 - a. Calculate the percentage of isopropylcylohexane...Ch. 5.6 - a. for which reaction in each set will S be more...Ch. 5.6 - a. For a reaction with H = 12 kcal/ mol and S =...Ch. 5.8 - Prob. 23PCh. 5.9 - Prob. 24PCh. 5.9 - How many different alkenes can be hydrogenated to...Ch. 5.9 - The same alkane is obtained from the catalytic...Ch. 5.9 - Prob. 27PCh. 5.9 - Rank the following compounds from most stable to...Ch. 5.10 - Prob. 29PCh. 5.10 - Prob. 30PCh. 5.11 - The rate constant for a reaction can be increased...Ch. 5.11 - Prob. 33PCh. 5.11 - a. Which reaction has a greater equilibrium...Ch. 5.12 - Draw a reaction coordinate diagram for a two-step...Ch. 5.12 - a. Which step in the reaction coordinate diagram...Ch. 5.12 - Draw a reaction coordinate diagram for the...Ch. 5.13 - Prob. 38PCh. 5 - What is each compounds systematic name?Ch. 5 - Prob. 40PCh. 5 - Draw the structure of a hydrocarbon that has six...Ch. 5 - Draw the condensed structure for each of the...Ch. 5 - Prob. 43PCh. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Name the following:Ch. 5 - Prob. 47PCh. 5 - Prob. 48PCh. 5 - Prob. 49PCh. 5 - In a reaction in which reactant A is in...Ch. 5 - Which bond is stronger? Briefly explain why.Ch. 5 - Prob. 52PCh. 5 - Prob. 53PCh. 5 - By following the curved red arrows, draw the...Ch. 5 - Prob. 55PCh. 5 - Prob. 56PCh. 5 - Draw structures for the following: a....Ch. 5 - Prob. 58PCh. 5 - a. Which of the following reactions has the larger...Ch. 5 - Prob. 60PCh. 5 - a. What is the equilibrium constant for a reaction...Ch. 5 - Prob. 62PCh. 5 - Prob. 63PCh. 5 - Given that the free energy of the twist-boat...Ch. 5 - Prob. 65PCh. 5 - Prob. 1PCh. 5 - Prob. 2PCh. 5 - Prob. 3PCh. 5 - Prob. 4PCh. 5 - Prob. 5PCh. 5 - Prob. 6PCh. 5 - Draw curved arrows to show the movement of the...Ch. 5 - Prob. 8PCh. 5 - Prob. 9PCh. 5 - Prob. 10P
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- The heat of combustion of either but-1-yne or but-2-yne is -2577 kJ/mol (-615.9 kcal/mol), whereas the other's is -2597 kJ/mol (-620.7 kcal/mol). Match each compound to its heat of combustion. But-1-yne But-2-ynearrow_forwardHow do you rank alkenes in order of their heats of hydrogenation? How do you know an alkene's heat of hydrogenation?arrow_forwardWhy 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?arrow_forward
- Draw the alkene that would react with the reagent given to account for the product formed. ? + + H₂O **** H₂S04 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. CH3 CH3 CHCCH3 | | OH CH3 +1arrow_forwardDraw the skeletal structure of each product for each reaction.arrow_forwardMatch each alkene to its heat of hydrogenation. Alkenes: 3-methylbut-1-ene, 2-methylbut-1-ene, 2-methylbut-2-ene ΔH° (hydrogenation) kJ/mol: –119, –127, –112arrow_forward
- What alkylborane is formed from hydroboration of each alkene?arrow_forwardName the three alkenes using systematic names. H3C CH3 A. H3C H. The name of compound A is: CH2 H2 В. CH3 H3C H2 The name of compound B is: Br H2C-CH2 CH3 С. H. CH3 B.arrow_forwardH,C -CH3 H,C -CH3 CH3 H,C CH structure 1 structure 2 Which is the more stable alkene? Explain your answer.arrow_forward
- a. What hydrocarbon with molecular formula C4H10 forms only two monochlorinated products? Both products are achiral. b. What hydrocarbon with the same molecular formula as in part a forms three monochlorinated products? One is achiral and two are chiral.arrow_forwardDraw the structure for an alkene that gives the following reaction product. CH3 HCI CH3CHCH2CHCH3 CI • Ignore alkene stereochemistry. •You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. P. opy aste ChemDoodle"arrow_forwardDraw the structure of each alkene of molecular formula C7H14 that has a tetrasubstituted double bondarrow_forward
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