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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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.) Why is the heat of hydrogenation of the cis isomer so much larger (more negative) than that of the trans isomer?
What two stereoisomeric alkanes are formed from the catalytic hydrogenation of (z)-3-methyl-2-hexene? Draw and label the alkanes. What are the relative amounts of each alkane?
Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.
1. HCl. 4.Br2 in CH2Cl2 7. H2O + H2SO4
2. BH3/THF, followed by HO-, H2O2, H2O 5. Br2 + H2O 8. CH3OH + H2SO4 3. a peroxyacid 6. H2 + Pd/C
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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- Which reaction intermediate is formed when 4-methylcyclohexene reacts with Br2 dissolved in CCl4arrow_forwarda. How many alkenes could you treat with H2, Pd/C to prepare methylcyclopentane? b. Which of the alkenes is the most stable? c. Which of the alkenes has the smallest heat of hydrogenation?arrow_forwardConsider a reaction where cis-but-2-ene is treated with OsO4 followed by NaHSO3/H2O. Draw the structure of one product that is formed in the reaction, including correct stereochemistry.arrow_forward
- Which of the following is most soluble in basic medium? a. cyclopropane b. 1,3-cyclobutadiene c. 1,3-cyclopentadiene d. benzenearrow_forwardThe 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_forwardExplain why heats of hydrogenation cannot be used to determine the relative stability of 2-methylpent-2-ene and 3-methylpent-1-ene. A, B, and C, each subjected to hydrogenation. The number of rings and π bonds refers to the reactant (A, B, or C) prior to hydrogenation.arrow_forward
- Which isomer of 1-bromo-3-isopropylcyclohexane reacts faster when refluxed with potassium tert-butoxide, the cis isomer or the trans isomer? Draw the structure of the expected product from the faster-reacting compound.arrow_forwardIgnoring stereochemistry, draw the alkylborane formed from the addition of one equivalent of BH3 to the alkene. The alkylborane formed in Part 1 is further treated with H2O2 and HO−. Draw the two stereoisomers of the final product of the reaction. Include stereochemistry where relevant. How many stereocenters are formed from the reaction? What is the relationship between the stereoisomers?arrow_forwardThe 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?arrow_forward
- Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forwardFollowing are structural formulas and heats of combustion of acetaldehyde and ethylene oxide. Which of these compounds is more stable? Explain.arrow_forwardA hydrocarbon of unknown structure has the formula C8H10. On catalytichydrogenation over the Lindlar catalyst, 1 equivalent of H2 is absorbed. Onhydrogenation over a palladium catalyst, 3 equivalents of H2 are absorbed.(a) How rnany degrees of unsaturation are present in the unknown?(b) How many triple bonds are present?(c) How many double bonds are present?(d) How many rings ar e present?(e) Draw a structure that fits the data.arrow_forward
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