Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 8, Problem 8.23P
Interpretation Introduction
Interpretation:
BDE of each indicated bond in cyclohexene has to be estimated.
Concept introduction:
Bond dissociation energy also measures the bond strength.
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1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product.
What is the theoretical yield of 2,4-pentanediol expressed in grams? Show calculations.
What is the percentage yield of pure 2,4-pentanediol?
1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product.
a.
Provide a balanced chemical equation to show the reaction between 1,4-pentadiene and sulfuric acid. Do not use molecular formulas in the chemical equation except for sulfuric acid.
b.
What reactant is the limiting reagent in this chemical equation? Show calculations to support your answer.
Chapter 8 Solutions
Organic Chemistry
Ch. 8.2 - Prob. 8.1PCh. 8.4 - Name and draw structural formulas for all...Ch. 8.4 - Using the table of bond dissociation enthalpies in...Ch. 8.5 - Prob. 8.4PCh. 8.6 - Given the solution to Example 8.5, predict the...Ch. 8.7 - Prob. 8.6PCh. 8.7 - Linoleic acid is shown below. What makes this...Ch. 8.7 - Prob. BQCh. 8.7 - Prob. CQCh. 8.7 - The strength of the HO bond in vitamin E is weaker...
Ch. 8.7 - Prob. EQCh. 8.8 - Prob. 8.7PCh. 8 - Prob. 8.8PCh. 8 - Prob. 8.9PCh. 8 - Prob. 8.10PCh. 8 - Prob. 8.11PCh. 8 - Account for the fact that among the chlorinated...Ch. 8 - Name and draw structural formulas for all possible...Ch. 8 - Prob. 8.14PCh. 8 - There are three constitutional isomers with the...Ch. 8 - Following is a balanced equation for bromination...Ch. 8 - Prob. 8.17PCh. 8 - Prob. 8.18PCh. 8 - Prob. 8.19PCh. 8 - Cyclobutane reacts with bromine to give...Ch. 8 - Prob. 8.21PCh. 8 - Following is a balanced equation for the allylic...Ch. 8 - Prob. 8.23PCh. 8 - Prob. 8.24PCh. 8 - The major product formed when methylenecyclohexane...Ch. 8 - Prob. 8.26PCh. 8 - Prob. 8.27PCh. 8 - Prob. 8.28PCh. 8 - Write the products of the following sequences of...Ch. 8 - Using your reaction roadmap as a guide, show...Ch. 8 - Prob. 8.31PCh. 8 - Prob. 8.32PCh. 8 - Prob. 8.33PCh. 8 - Prob. 8.34P
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- Write the monobromination products of 1,4-dimethylcyclohexane and calculate the percentages of each product. Which is the major product?arrow_forwardif the heat of hydrogenation for cyclohexene is 120 kj mol and 1,3 cyclohexane is less than 240 kj mol, what is the heat of hydrogenation for benzene? thank you ^___^arrow_forwardDraw the structure(s) of all of the alkene isomers, C5H10, that contain a branched chain. Consider E/Z stereochemistry of alkenes.arrow_forward
- The heat of combustion of decahydronaphthalene(C10H18) is -6286 kJ/mol. The heat of combustion ofnaphthalene (C10H8) is -5157 kJ/mol. (In both casesCO2(g) and H2O(l) are the products.) Calculate the heat of hydrogenationand the resonance energy of naphthalene.arrow_forwardHow many vinylic hydrogens does cyclopentene have?arrow_forwardUsing the table of bond dissociation enthalpies , calculate ▲H° for bromination of propane to give 2-bromopropane and hydrogen bromide.arrow_forward
- 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.) 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_forwardDerive the structure of 3 - Nitrocyclohexene.arrow_forwardRead Appendix B on naming branched alkyl substituents, and draw all possible alkyl groups having the formula C5H11–. Give the IUPAC names for the eight compounds of molecular formula C10H20 that contain a cyclopentane ring with each of these alkyl groups as a substituent.arrow_forward
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