Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 4.3, Problem 9P
cis-1, 2-Dimethylcyclopropane has more strain than trans-l, 2-dimethylcyclo propane. How can you account for this difference? Which of the two com pounds is more stable?
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Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Which compound is more stable: cis-1,2-dimethylcyclopropane or trans-1,2- dimethylcyclopropane? Explain your answer.arrow_forwardHow to draw the more stable conformer of trans-1-ethyl-2-methylcyclohexane? Thank you.arrow_forwardRank the conformations of n-butane with reference to its potential energy from the most stable to the least stable. Rank from the most stable to the least stable. To rank items as equivalent, overlap them.arrow_forward
- Rank the conformations of n-butane with reference to its potential energy from the most stable to the least stable. Rank from the most stable to the least stable.To rank items as equivalent, overlap them.arrow_forward4. Which structure below represents the most stable conformation of cis-1-t-butyl-4-methylcyclohexane? A B D 5. The planar form of which ring would have bond angles close to the tetrahedral value, but is destabilized by eclipsing interactions (torsional strain)? Which of the following statements about conformations is FALSE? A) Conformations can be isolated and separated at room temperature B) Conformations are interconverted by rotation about o-bonds C) For butane the staggered anti conformation is the most stable D) For ethane the eclipsed conformation is the least stable 6. 7. Which of the following compounds has two chirality centers? .H H. H3Carrow_forwardDraw both the condensed and line-bond structure of these 4 compounds: * 4-ethylcycloheptene * 4,4-dimethylpent-2-ene * 3-chloro-2,7-dimethylnon-4-yne (Cl- Chloro branch) * 1-cyclohexylbut-2-ynearrow_forward
- When cyclopropane is treated with HI, 1-idopropane is formed. A similar type of reaction does not occur with cyclopentene or Cyclohexane. Suggest an explanation for cyclopropane’s reactivity.arrow_forward8. The heat of combustion (per CH₂) of several cycloalkanes is listed below. Based on the data given, which of these cycloalkanes would be considered most stable? Heat of combustion (kJ/CH₂) -686.5 -664.0 -663.6 -659.0 (A) cyclobutane (C) cyclooctane Cycloalkane cyclobutane cyclopentane cyclooctane cyclopentadecane (B) cyclopentane (D) cyclopentadecanearrow_forward5. Complete the following reactons: H,SO, H3C-CH CH2 + H,O CH3 H3C-CH=Ċ -CH2 + H,O H,SO,arrow_forward
- 11. s) Draw the most stable conformation of 1,3-dichloro-2,4-difluorocyclohexane: 12. Which of the following represents the most stable conformation of 1,2,4,5- tetramethyleyclohexane? (one correct answer) CH b) CH HC H- H- CH HC CH, CH 6. Give IUPAC name for the following molecule. Include "cis" and "trans" designations if applicable. H2C-CH3 H -CH2 H- H Brarrow_forwardDraw the most and least stable conformer of chloroethane and 1,2-dibromoethane.arrow_forwardDraw the structure of cis-1,2-dimethylcyclohexane. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. opy astearrow_forward
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