Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
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?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Among the structuresWhat is the structure for the trans-1,2-dimethylcyclohexane?What is the structure for cis-1-propyl-2-methylcyclohexane?
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.
Which of the following structures completes the resonance equation shown below?
CH;-0-CH,
CH;-0-CH2
CH;-0-CH3
CH;-0-CH3
CH3-0=CH,
CH;-0=CH2
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...
Knowledge Booster
Learn more about
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
- 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_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_forward5. Complete the following reactons: H,SO, H3C-CH CH2 + H,O CH3 H3C-CH=Ċ -CH2 + H,O H,SO,arrow_forward
- 8. 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_forward11. 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_forwardThese are different isomers for C4H8O. Which structure would not be an isomer of butanal?arrow_forward
- Name the following molecule. CH₂CH3 H-CH3 H3C H Br (2R, 3R)-2-bromo-3-methylpentane (2S,3S)-2-bromo-3-methylpentane O (2R,3S)-2-bromo-3-methylpentane (1R, 2S)-1-bromo-1,2-dimethylbutane (1S,2R)-1-bromo-1,2-dimethylbutanearrow_forwardWhy is a substituted cyclohexane ring more stable with a larger group in the equatorial position?arrow_forwardDraw an expanded structural formula of pent-1-en-3-yne/ CH3-CC-CH=CH2 and then label each carbon. Indicate the longest and shortest C-H bond and predict the C—C single bond that has the highest BDE(bond dissociation energy).arrow_forward
- Name or draw the following compounds: Chemical structure IUPAC Name r-on, 1 H;C-CH;-CH-CH, ÇH3 2 H,C-ÇH-CH,-HC-CH, ČH3 Br Br ÇI -CH3 3 H,C-CH-CH,-CH-CH-C- CH, CI CH, H,C-ÇH-CH,--CH;-CH3 ČH3 4 CH3 HC-CH,-CH- ÇH2 Ci-CH CH3 CH-CH, 5 CIarrow_forward13. 14. A F A CI Br The name of A is 2-fiuoro-3-chloro-4-bromohexene The name of A is 4-bromo-3-chloro-2-fluorohexene The name of A is 4-bromo-3-chloro-2-fluorohexane |The name of A is oct-1-yne The name of A is oct-2-yne The name of A is oct-1-ene The name of A is oct-2-ene |The name of A is 3-bromo-2-chloro-1-fluorohexane 15. 16. H HN-C-0: A нн нO F JA and B are the same molecules jA and B are different molecules F OH The formal charges are correct, and the ionic charge is correct The formal charges are correct, but the ionic charge is incorrect 17. 18. DA catalyst changes E,, and it also changes AG JA catalyst changes E,, but it does not change AG With a catalyst, reactions become slower Br, NH2 HN. B HYCI With a catalyst, the reaction rate remains the same H CI OB is the correct Newman projection of A |B is not the correct Newman projection of A OODO O000arrow_forwardConstruct the chair structures with the molecular models for trans-1-ethyl-3-methylcyclohexane. Find the energy of each conformer, the equilibrium constant Keq, and the percentage of each conformer at 25oC. Indicate which conformer is more stable.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry: Principles and PracticeChemistryISBN:9780534420123Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward MercerPublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Chemistry: Principles and Practice
Chemistry
ISBN:9780534420123
Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License