Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 5.9, Problem 26P
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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?
Which one of the statements below is wrong about Zaitsev’s Rule.
a.
None of the above
b.
The Zaitsev’s Rule demonstrate the principle of regioselectivity in elimination reactions
c.
The more substituted alkene is the major product of E1 or E2 elimination
d.
The more substituted alkane product is obtained when a proton is removed from β-carbon that is bonded to the fewest hydrogens
e.
The most stable alkene is generally the major product
How process of ring-flipping also affects the orientation of cyclohexane's hydrogen atoms ?
Chapter 5 Solutions
Organic Chemistry (8th Edition)
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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- A 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_forwardAxial alcohols are oxidized faster than equatorial alcohols by PCC and other Cr6+ oxidants. Which OH group in each compound is oxidized faster?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
- Consider the four trienes E–H. Rank compounds E–H in order of increasing heat of hydrogenation.arrow_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_forwardMost methods of making alkenes yield predominately the more stable isomer, usually the trans. Outline all steps in the conversion of a mixture of 75% trans-2-pentene and 25% cis-2-pentene into essentially pure cis-2-pentene.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_forwardWhat two stereoisomeric alkanes are formed in the catalytic hydrogenation of (Z)-3-methyl-2-hexene? Draw and label the alkanes. In this reaction, what are the relative amounts of each of the two alkanes generated?arrow_forwardDraw all stereoisomers formed by monochlorination of the cis andtrans isomers of 1,2-dimethylcyclobutane drawn below.arrow_forward
- 1. What are the various ways by which alkenes may be synthesized?2. Give two examples each of Unsymmetrical alkenes and reagents.3. Give two examples of reactions of alkenes that result in Anti-Markonikov’s addition productsarrow_forward9. Upon hydrogenation, which of the following alkenes releases the least heat per mole?arrow_forwardDraw 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/Carrow_forward
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