Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 5.6, Problem 11P
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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?
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 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.
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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- Following are structural formulas and heats of combustion of acetaldehyde and ethylene oxide. Which of these compounds is more stable? Explain.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_forwardHow do you rank alkenes in order of their heats of hydrogenation? How do you know an alkene's heat of hydrogenation?arrow_forward
- H,C -CH3 H,C -CH3 CH3 H,C CH structure 1 structure 2 Which is the more stable alkene? Explain your answer.arrow_forwardThe 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_forwardName each compound in which the benzene ring is best treated as a substituent. CH3 a. CH3-CH-CH,-CH-CH,-CH–CH,-CH; CH,-CH3 b. CH,-CH-CH=CH-CH,-CH,–CH,-CH, c. CH3-C=C-CH-CH-CH-CH2-CH3 CH3 CH3arrow_forward
- Match 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_forwarda. The following compounds have the same molecular formula as benzene. How many monobrominated products could each form? 1. HC‚CC‚CCH2CH3 2. CH2“CHC‚CCH“CH2 b. How many dibrominated products could each of the preceding compounds form? (Do not include stereoisomers.) c. How many dibrominated products could each of the compounds form if stereoisomers are included?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 a structural formula for the alkene you would use to prepare the alcohol shown by hydroboration/oxidation. OH AFFIL CH3 CH3 H • 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. Sn [F ? ChemDoodlearrow_forwardDraw all constitutional isomers formed when each alkene is treated with NBS + hv. -CH3 CH c. CH2=C(CH2CH3)2 a. CH,CH=CHCH3 b.arrow_forwardDraw the skeletal structure of each product for each reaction.arrow_forward
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