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 4.4, Problem 11P
Two conformations of cis-l, 3-dimethylcyclobutane are shown. What is the difference between them, and which do you think is likely to be more stable?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
(c)
Draw the most likely conformations of the following compounds H and J
and explain your reasoning.
Ph
OMe
H
Br
OH
CO₂Me
J
Draw (1R,3S)-1,3-dimethylcyclohexane, in its minimum energy conformation. Then draw the Newman Projection for this structure with the correct stereochemistry and in its minimum energy state.
Which chair conformation of cis- and trans-1,4-dimethylcyclohexane has the lowest potenital energy? Which is the most stabel? Why?
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
- Consider the molecule 1-bromo-2-methylbutane. C3 and C4 should be drawn as Et as in theexample. This group is called an ethyl group and can be considered a sphere about twice the sizeof a methyl group. Draw the following Newman projections sighting down the C1C2 bond... a. The lowest potential energy conformation. b. The highest potential energy staggered conformation.arrow_forwardGive the most stable conformation for (1S, 2S)-1-methoxy-2-chlorocyclohexane.arrow_forwardDraw the highest and lowest energy conformations. In cases where two or three conformations are degenerate, choose only one as your anwser. Use Pr, Me, H, Et in the structures.arrow_forward
- Draw the planar (Haworth) structure for cis-1-ethyl-2- methylcyclohexane. (b) Draw the two ring - flipped chair conformations. (c) Circle the more stable chair conformation (circle both if they are equal in energy). Draw the Haworth structure and the two ring-flipped conformations of 1, 2, 4- trimethylcyclohexane (Compound D) on the frames below, b) Circle the more stable chair conformation (circle both if they are equal in energy). Haworth Structurearrow_forwardIs the following compound R or S. Support your claim by indicating the priority ofthe groups attached to the asymmetric carbon. H,CCH, *CH,OCH, CIarrow_forwardIn each case below, draw the highest and lowest energy conformations. If there are cases where there are 2 or 3 confirmations that are degenerate, choose only one as the anwser.arrow_forward
- Rank the following conformers in order of decreasing stability, putting the most stable first. H CH₂CH3 CH3 CH₂CH3 H O I > I > II > III ON> I > I|| > || OIII>I> IV> || O II > IV > I > III ON>I>II> III CH³CH₂ CH3 CH₂CH3 CH3CH₂ CH3 H H H 4 CH₂CH3 CH3CH₂ H CH₂CH3 H IV CH3 Harrow_forward| Which of the following compounds is more stable? To get credit you must draw the most stable chair conformation of each compound and explain your answer.arrow_forwardConsider compound Q shown below (trimethylcyclohexane isomer). compound Q Which of the following is the most stable conformation of compound Q? I ||| CH3 Select one: O A. II OB. I O C. III O. D. IV H CH3 H CH3 H H- CH3 CH3 H CHS ||| H IV CH3 H CH₁ CH3 fff, H CH3 CH3 CH3arrow_forward
- In each case below, identify the higest and lowest energy conformations. In cases where two or three conformations are degenerate, choose only one as your anwser. Use Me, H, and Et when drawing the structures.arrow_forwardWhich of these shows the s-trans conformation of (2Z,4Z)-3-ethyl-2,4-hexadiene?arrow_forwardThe highest energy conformation of ethane has 12 kJ/mol of strain. The two highest conformations of butane have 16 and 19 kJ/mol of strain, respectively. How much strain does the highest energy conformation of 2,3-dimethylbutane have?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
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