Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
2nd Edition
ISBN: 9780393655551
Author: KARTY, Joel
Publisher: W. W. Norton & Company
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Chapter 14, Problem 14.44P
Interpretation Introduction
Interpretation:
Whether molecule
Concept introduction:
The heat of hydrogenation is the amount of energy released when a hydrogen molecule is added to a double or triple bond. It is based on the stability of
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Draw a stereoisomer of cis-1,2-dimethylcyclohexane.
(Note that the question asks for a different stereoisomer of the named compound and not the named compound itself.)
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• In cases where there is more than one answer, just draw one.
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The heat of combustion of cis-1,2-dimethylcyclopropane is larger than that of the trans isomer. Which isomer is more stable? Use drawings to explain this difference instability.
3. For each pair, predict which conformation is more stable and explain the physical reason
for the difference in stability.
Chapter 14 Solutions
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
Ch. 14 - Prob. 14.1PCh. 14 - Prob. 14.2PCh. 14 - Prob. 14.3PCh. 14 - Prob. 14.4PCh. 14 - Prob. 14.5PCh. 14 - Prob. 14.6PCh. 14 - Prob. 14.7PCh. 14 - Prob. 14.8PCh. 14 - Prob. 14.9PCh. 14 - Prob. 14.10P
Ch. 14 - Prob. 14.11PCh. 14 - Prob. 14.12PCh. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - Prob. 14.15PCh. 14 - Prob. 14.16PCh. 14 - Prob. 14.17PCh. 14 - Prob. 14.18PCh. 14 - Prob. 14.19PCh. 14 - Prob. 14.20PCh. 14 - Prob. 14.21PCh. 14 - Prob. 14.22PCh. 14 - Prob. 14.23PCh. 14 - Prob. 14.24PCh. 14 - Prob. 14.25PCh. 14 - Prob. 14.26PCh. 14 - Prob. 14.27PCh. 14 - Prob. 14.28PCh. 14 - Prob. 14.29PCh. 14 - Prob. 14.30PCh. 14 - Prob. 14.31PCh. 14 - Prob. 14.32PCh. 14 - Prob. 14.33PCh. 14 - Prob. 14.34PCh. 14 - Prob. 14.35PCh. 14 - Prob. 14.36PCh. 14 - Prob. 14.37PCh. 14 - Prob. 14.38PCh. 14 - Prob. 14.39PCh. 14 - Prob. 14.40PCh. 14 - Prob. 14.41PCh. 14 - Prob. 14.42PCh. 14 - Prob. 14.43PCh. 14 - Prob. 14.44PCh. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - Prob. 14.47PCh. 14 - Prob. 14.48PCh. 14 - Prob. 14.49PCh. 14 - Prob. 14.50PCh. 14 - Prob. 14.51PCh. 14 - Prob. 14.52PCh. 14 - Prob. 14.53PCh. 14 - Prob. 14.54PCh. 14 - Prob. 14.55PCh. 14 - Prob. 14.56PCh. 14 - Prob. 14.57PCh. 14 - Prob. 14.58PCh. 14 - Prob. 14.59PCh. 14 - Prob. 14.60PCh. 14 - Prob. 14.61PCh. 14 - Prob. 14.62PCh. 14 - Prob. 14.63PCh. 14 - Prob. 14.64PCh. 14 - Prob. 14.65PCh. 14 - Prob. 14.66PCh. 14 - Prob. 14.1YTCh. 14 - Prob. 14.2YTCh. 14 - Prob. 14.3YTCh. 14 - Prob. 14.4YTCh. 14 - Prob. 14.5YTCh. 14 - Prob. 14.6YTCh. 14 - Prob. 14.7YTCh. 14 - Prob. 14.8YTCh. 14 - Prob. 14.9YTCh. 14 - Prob. 14.10YTCh. 14 - Prob. 14.11YTCh. 14 - Prob. 14.12YTCh. 14 - Prob. 14.13YT
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- Which of the following statement is false about conjugated systems? A conjugated system is more stable than an unconjugated A system. The s-trans isomer is favored over the s-cis isomer. A conjugated system has C multiple resonance structures. A conjugated system can only D contain two alkenes.arrow_forwardHello, I was reading an answer from the book Organic Chemistry by Brown et al. The question is 2.51 "Draw alternative chair conformations for each substituted cyclohexane and state which chair is more stable." There are then 4 cyclohexanes (labeled a-d). For the "a" cyclohexane, the substituents are arranged as a combination of axial and equatorial in both chair conformations. However, for the "b," "c," and "d," cyclohexanes one chair has only equatorial substituents, and the other chair has only axial substituents. Why is the "a" chair conformation different? https://www.bartleby.com/solution-answer/chapter-2-problem-251p-organic-chemistry-8th-edition/9781305580350/draw-alternative-chair-conformations-for-each-substituted-cyclohexane-and-state-which-chair-is-more/4532cd91-c341-11e9-8385-02ee952b546earrow_forwardDraw all constitutional isomers of all-cis ethylmethylisopropylcyclohexane—that is, in which a methyl group (CH3), an ethyl group (CH2CH3), and an isopropyl group [CH(CH3)2] are all bonded to a cyclohexane ring on the same side of the ring’s plane. Which of those isomers do you think is the most stable? Explainarrow_forward
- The energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).arrow_forward3) Draw a cyclohexane chair with 3 substituents in the most stable conformation. Explain why the conformation you've chosen is the most stable.arrow_forward(a) which if the structure of trans-1,2-dimethylcyclopentane? (b) which is the most stable conformation of 1-bromo-2-ethylcyclohexane? (c) which is the least stable conformation of 1-bromo-2-ethylcyclohexane? (d) which is the more stable configuration of 1,3-dimethylcyclopentane? *Et = ethylarrow_forward
- What is the total strain energy of 2,2-dimethylpropane in an eclipsed conformation? Given: For CH3 eclipsed to H (both attached to adjacent C's), the total strain energy is 6 kJ/mol. Select one: A. 12 kJ В. 18 kJ С. 21 kJ D. 11.4 kjarrow_forwardDraw all the possible conformations of trans- and cis-1,3-dimethylcyclobutane. Which of these conformations is the most stable conformation? Explain your answer. Discuss the type of strain(s) that affect the stability of these compounds.arrow_forwardtrans-1,4-dimethylcyclohexane has two conformations with a difference in energy of 3.6 kcal/mol. What is the cause of this difference? Hint: this is twice the difference in methylcyclohexane!arrow_forward
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