Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 5, Problem 23P
Which of the following compounds is the most stable? Which is the least stable?
3,4-dimethyl-2-hexene; 2,3-dimethyl-2-hexene; 4,5-dimethyl-2-hexene
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Which of the following alkenes is the most stable?
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 5 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 5.1 - Prob. 1PCh. 5.1 - Draw the structure for each of the following: a....Ch. 5.1 - What is each compounds systematic name?Ch. 5.3 - Prob. 4PCh. 5.3 - Prob. 5PCh. 5.3 - Prob. 7PCh. 5.4 - a. For which reaction in each set below will S be...Ch. 5.6 - Prob. 9PCh. 5.6 - How many different alkenes can be hydrogenated to...Ch. 5.6 - The same alkane is obtained from the catalytic...
Ch. 5.6 - Prob. 12PCh. 5.6 - Rank the following compounds in order from most...Ch. 5.7 - The rate constant for a reaction can be increased...Ch. 5.7 - Prob. 15PCh. 5.7 - Prob. 16PCh. 5.9 - Draw a reaction coordinate diagram for a two-step...Ch. 5.9 - Prob. 18PCh. 5.9 - Draw a reaction coordinate diagram for the...Ch. 5.10 - Which of the following parameters would be...Ch. 5 - What is each compounds systematic name?Ch. 5 - Draw the structure of a hydrocarbon that has six...Ch. 5 - Which of the following compounds is the most...Ch. 5 - Prob. 24PCh. 5 - Prob. 25PCh. 5 - Prob. 26PCh. 5 - Prob. 27PCh. 5 - Name the following:Ch. 5 - Prob. 29PCh. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Name each of the following:Ch. 5 - Prob. 38PCh. 5 - Given that the twist-boat conformer of cyclohexane...Ch. 5 - a. The G for conversion of axial fluorocyclohexane...Ch. 5 - Prob. 1PCh. 5 - Prob. 2PCh. 5 - Prob. 3PCh. 5 - Prob. 4PCh. 5 - Prob. 5PCh. 5 - Prob. 6PCh. 5 - Prob. 7PCh. 5 - Prob. 8PCh. 5 - Prob. 9PCh. 5 - Prob. 10P
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- Draw the structures of the following molecules: (a) trans-l-Bromo-3-methylcyclohexane (b) cis-1, 2-Dimethylcyclobutane (c) trans-1 -tert-Butyl-2-ethylcyclohexanearrow_forwardPlease do the following . 2-butyne + HgSO4, H2SO4 and H2O 2-methyl-1,3-butadiene + HC ≡ C – C ≡ Narrow_forwardPredict the products of the following reactions. cyclopentadiene + methyl acrylate, CH2“CH¬COOCH3arrow_forward
- Which of the structures below is (4R)-4ethyl-2,4- dimethylcyclohexan-1-one?arrow_forwardDraw the compunds below. (2e,4z)-1-bromo-4-methylhexa-2,4-diene (2e,4z)-5-bromo-3-methylhexa-2,4-diene (2z,4e)-1-bromo-4-methylhexa-2,4-diene (2z,4e)-1-bromo-3-methylhexa-2,4-dienearrow_forwardwhich one of the following cycloalkanes will be least stable? (a) cyclopropane (b) cyclobutane (c) cyclopentan (d) cyclohexanearrow_forward
- Please draw the line structures of all of the C8H17+ carbocations that have the carbon-skeleton below. And circle the most stable carbocation of those drawn.arrow_forwardDraw a structural formula for the most stable carbocation with each molecular formula. Q.) C5H11+arrow_forward12-77 Show how to convert cyclopentene into these compounds. 1,2-Dibromocyclopentane Cyclopentanol Iodocyclopentane Cyclopentanearrow_forward
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