Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
expand_more
expand_more
format_list_bulleted
Question
Chapter 4, Problem 4.73P
Interpretation Introduction
Interpretation:
The reason for more stability of
Concept introduction:
In monosubstituted compounds, the equatorial substituted conformer is more stable than the axial conformer due to 1, 3 diaxial interactions. But this depends on the substituent present on it. If the substituent is a hydroxyl group (OH group) present in axial position and can form hydrogen bonding with adjacent or near atoms like oxygen, then it prefers to occupy the axial position only.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Below are isomers of tert-butylcyclohexanol in conformational structures. Two are cis-2-tert-
butylcyclohexanol and two are cis-3-tert-butylcyclohexanol. Indicate which is the more stable conformation
for each pair, and indicate which of all four conformations is the most stable.
A
OH
Ex
HO
B
D
OH
OH
Why is a substituted cyclohexane ring more stable with a larger group in the equatorial position?
Name and draw structural formulas for the eight constitutional isomeric alcohols with molecular formula C5H12O. Classify each alcohol as primary, secondary, or tertiary. Which are chiral?
Chapter 4 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 4 - Prob. 4.1PCh. 4 - Prob. 4.2PCh. 4 - Prob. 4.3PCh. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Prob. 4.6PCh. 4 - Prob. 4.7PCh. 4 - Prob. 4.8PCh. 4 - Prob. 4.9PCh. 4 - Prob. 4.10P
Ch. 4 - Prob. 4.11PCh. 4 - Prob. 4.12PCh. 4 - Prob. 4.13PCh. 4 - Prob. 4.14PCh. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Prob. 4.17PCh. 4 - Prob. 4.18PCh. 4 - Prob. 4.19PCh. 4 - Prob. 4.20PCh. 4 - Prob. 4.21PCh. 4 - Prob. 4.22PCh. 4 - Prob. 4.23PCh. 4 - Prob. 4.24PCh. 4 - Prob. 4.25PCh. 4 - Prob. 4.26PCh. 4 - Prob. 4.27PCh. 4 - Prob. 4.28PCh. 4 - Prob. 4.29PCh. 4 - Prob. 4.30PCh. 4 - Prob. 4.31PCh. 4 - Prob. 4.32PCh. 4 - Prob. 4.33PCh. 4 - Prob. 4.34PCh. 4 - Prob. 4.35PCh. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - Prob. 4.38PCh. 4 - Prob. 4.39PCh. 4 - Prob. 4.40PCh. 4 - Prob. 4.41PCh. 4 - Prob. 4.42PCh. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - Prob. 4.45PCh. 4 - Prob. 4.46PCh. 4 - Prob. 4.47PCh. 4 - Prob. 4.48PCh. 4 - Prob. 4.49PCh. 4 - Prob. 4.50PCh. 4 - Prob. 4.51PCh. 4 - Prob. 4.52PCh. 4 - Prob. 4.53PCh. 4 - Prob. 4.54PCh. 4 - Prob. 4.55PCh. 4 - Prob. 4.56PCh. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - Prob. 4.59PCh. 4 - Prob. 4.60PCh. 4 - Prob. 4.61PCh. 4 - Prob. 4.62PCh. 4 - Prob. 4.63PCh. 4 - Prob. 4.64PCh. 4 - Prob. 4.65PCh. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Prob. 4.68PCh. 4 - Prob. 4.69PCh. 4 - Prob. 4.70PCh. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 4 - Prob. 4.73PCh. 4 - Prob. 4.1YTCh. 4 - Prob. 4.2YTCh. 4 - Prob. 4.3YTCh. 4 - Prob. 4.4YTCh. 4 - Prob. 4.5YTCh. 4 - Prob. 4.6YTCh. 4 - Prob. 4.7YTCh. 4 - Prob. 4.8YTCh. 4 - Prob. 4.9YTCh. 4 - Prob. 4.10YTCh. 4 - Prob. 4.11YTCh. 4 - Prob. 4.12YTCh. 4 - Prob. 4.13YTCh. 4 - Prob. 4.14YTCh. 4 - Prob. 4.15YTCh. 4 - Prob. 4.16YTCh. 4 - Prob. 4.17YTCh. 4 - Prob. 4.18YTCh. 4 - Prob. 4.19YTCh. 4 - Prob. 4.20YTCh. 4 - Prob. 4.21YTCh. 4 - Prob. 4.22YTCh. 4 - Prob. 4.23YTCh. 4 - Prob. 4.24YTCh. 4 - Prob. 4.25YT
Knowledge Booster
Similar questions
- Draw the most stable structure of cis-1-tbutyl-2-methylcyclohexane. Your structure should clearly distinguish between axial and equatorial positions.arrow_forwardHow many possible stereoisomers can be written for 1-ethyl-3- methylcyclohexane? O 2 O4 8arrow_forwardHow many chirality centers exist on this molecule? What is the absolute configuration of the primary alcohol in this structure? How many lone pairs are on the structure? How many sp2 hybridized atoms are on the structure?arrow_forward
- On a cyclohexane ring, an axial carboxyl group has a conformational energy of 5.9 kJ (1.4 kcal)/mol relative to an equatorial carboxyl group. Consider the equilibrium for the alternative chair conformations of trans-1,4-cyclohexanedicarboxylic acid. Draw the less stable chair conformation on the left of the equilibrium arrows and the more stable chair on the right. Calculate DG0 for the equilibrium as written and calculate the ratio of the more stable chair to the less stable chair at 25°C.arrow_forwardAre the hydroxyl groups on rings A, B, and C axial or equatorial to their respective rings?arrow_forwardConsider the molecule trans-1-ethyl-2-methylcyclohexane. What can you say about the most stable form of this molecule? O The ethyl is axial and the methyl is equatorial O The methyl is axial and the ethyl is equatorial Both substituents are axial Both substituents are equatorialarrow_forward
- A 1, 2-cis disubstituted cyclohexane, such as cis-1, 2-dichlorocyclohexane, must have one group axial and one group equatorial. Explain.arrow_forwardArrange these compounds in order of increasing boiling point (values in C are 42, 24, 78, and 118). (a) CH3CH2OH (b) CH3OCH3 (c) CH3CH2CH3 (d) CH3COOHarrow_forwardWhen (1-bromoethyl)cyclopentane is heated in water for an extended period of time, SIX products result: three alcohols and three alkenes. Draw the three alcoholsarrow_forward
- Which is the most stable conformation of the following alcohols? In general, how do I find the most stable conformation?arrow_forward2,4,6-Trinitrophenol is known by the common name picricacid. Picric acid is a solid but is readily soluble in water. Insolution, it is used as a biological tissue stain. As a solid,it is also known to be unstable and may explode. In thisway, it is similar to 2,4,6-trinitrotoluene (TNT). Draw thestructures of picric acid and TNT. Why is picric acid readily soluble in water, whereas TNT is not?arrow_forwardDraw structural formulas for the cis and trans isomers of hydrindane. Show each ring in its most stable conformation. Which of these isomers is more stable?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning