EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 5.9, Problem 26P
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4. The enthalpies, AH°, for the hydrogenation of three alkenes are shown below:
Alkene A: -50 kcal/mole
Alkene B: -60 kcal/mole
Alkene C: -70 kcal/mole
Which alkene is the least stable and why?
Draw the alkene that would react with the reagent given to account for the product formed.
CH3
HCI
CH3 CHCCH,
? +
Či CH3
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.
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-yne
Chapter 5 Solutions
EBK ORGANIC CHEMISTRY
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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- How do you rank alkenes in order of their heats of hydrogenation? How do you know an alkene's heat of hydrogenation?arrow_forwarda. 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?arrow_forwardDraw 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_forward
- Several factors can affect alkene stability. Explain why alkene A is more stable than alkene B even though both contain disubstituted carbon–carbon double bonds.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_forwardRank the alkenes from most stable to least stable.arrow_forward
- Predict the energy difference between pent-1-ene and cis-pent-2-ene.arrow_forwardDehydrohalogenation of 1-chloro-1-methylcyclopropane affords two alkenes (A and B) as products. Explain why A is the major product despite the fact that it contains the less substituted double bond.arrow_forwardDraw the structural formula for the product formed upon hydroboration/oxidation of the Alkene below.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 alternative chair conformations for the product formed by the addition of bromine to 4-tert-butylcyclohexene. The Gibbs free energy differences between equatorial and axial substituents on a cyclohexane ring are 21 kJ (4.9 kcal)/mol for tert-butyl and 2.0–2.6 kJ (0.48–0.62 kcal)/mol for bromine. Estimate the relative percentages of the alternative chair conformations you drew in the first part of this problemarrow_forward
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