ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 3, Problem 43P
In each of the following groups of compounds, identify the one with the largest heat of combustion and the one with the smallest. In which cases can a comparison of heats of combustion be used to assess relative stability?
Cyclopropane, cyclobutane, cyclopentane
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
1.
Explain which of cis-1,3-dimethylcyclohexane and trans-1,3-
dimethylcyclohexane has the highest enthalpy of combustion in the gas
phase, and which of cis-1,4-dimethylcyclohexane and trans-1,4-dimethylcyclohexane has the
highest enthalpy of combustion in the gas phase. Use diagrams to help explain your answer.
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) cyclopentadecane
Rank the following compounds according to heat of combustion with 1 being greatest exothermicity and 4 least exothermicity of combustion.
Chapter 3 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
Ch. 3.1 - Identify the alkanes corresponding to each of the...Ch. 3.1 - Find the conformations in Figure 3.4 in which the...Ch. 3.2 - Sketch a potential energy diagram for rotation...Ch. 3.2 - Acetylcholine is a neurotransmitter in the central...Ch. 3.2 - Prob. 5PCh. 3.5 - The heats of combustion of ethylcyclopropane and...Ch. 3.8 - Prob. 7PCh. 3.10 - The following questions relate to a cyclohexane...Ch. 3.10 - Draw the most stable conformation of...Ch. 3.11 - Prob. 10P
Ch. 3.11 - Prob. 11PCh. 3.12 - Based on what you know about disubstituted...Ch. 3.12 - Write structural formulas for the most stable...Ch. 3.14 - Cubane (C4H8) is the common name of the polycyclic...Ch. 3.14 - Prob. 15PCh. 3.14 - Prob. 16PCh. 3.14 - Prob. 17PCh. 3.14 - Prob. 18PCh. 3.15 - Prob. 19PCh. 3 - Give the IUPAC names of each of the following: (a)...Ch. 3 - Draw Newman projections for the gauche and...Ch. 3 - Identify all atoms that are (a) anti and (b)...Ch. 3 - Prob. 23PCh. 3 - Prob. 24PCh. 3 - Prob. 25PCh. 3 - Prob. 26PCh. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Oxidation of 4-tert-butylthiane proceeds according...Ch. 3 - The following are representations of two forms of...Ch. 3 - Draw (a) a Newman projection of the most stable...Ch. 3 - Write a structural formula for the most stable...Ch. 3 - Sight down the C-2-C-3 bond, and draw Newman...Ch. 3 - Prob. 34PCh. 3 - Sketch an approximate potential energy diagram for...Ch. 3 - Prob. 36PCh. 3 - Even though the methyl group occupies an...Ch. 3 - Which do you expect to be the more stable...Ch. 3 - Arrange the trimethylcyclohexane isomers shown in...Ch. 3 - Identify the more stable stereoisomer in each of...Ch. 3 - One stereoisomer of 1,1,3,5-tetramethylcyclohexane...Ch. 3 - One of the following two stereoisomers is...Ch. 3 - In each of the following groups of compounds,...Ch. 3 - The heats of combustion of the more and less...Ch. 3 - The measured dipole moment of ClCH2CH2Cl is 1.12D....Ch. 3 - Prob. 46PCh. 3 - Prob. 47PCh. 3 - Prob. 48DSPCh. 3 - Prob. 49DSPCh. 3 - Prob. 50DSPCh. 3 - Prob. 51DSPCh. 3 - Prob. 52DSPCh. 3 - Prob. 53DSP
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
- Following are structural formulas for 1,4-dioxane and piperidine. 1,4-Dioxane is a widely used solvent for organic compounds. Piperidine is found in small amounts in black pepper (Piper nigrum). (a) Complete the Lewis structure of each compound by showing all unshared electron pairs. (b) Predict bond angles about each carbon, oxygen, and nitrogen atom. (c) Describe the most stable conformation of each ring and compare these conformations with the chair conformation of cyclohexane.arrow_forwardClassify the following compounds as E/Z- structures CH3 HO-CH2-CH2 CH2CHCH2OH H2N CH2-CH3 H2N CH=CH2 CH2=CH I CH-CH3 но- CH II CH2-NH2 Br CH2CH2CH2CH3 III CH3 OHarrow_forwardBuild trans-1,4-dichlorocyclohexane of chair form. Build cis-1,4-dichlorocyclohexanes of chair form. Which one is more stable of cis-1,4-dichlorocyclohexane and trans-1,4-dichlorocyclohexane? Draw their conformations that show the chloro atoms in axial or equatorial positions.arrow_forward
- Rank the following compounds from most stable to least stable: trans-3-hexene, cis-3-hexene, cis-2,5-dimethyl-3-hexene, cis-3,4-dimethyl-3-hexenearrow_forwardThe most stable dimethylcyclohexane is trans-1,4-dimethylcyclohexane; cis-1,4-dimethylcyclohexane; trans-1,3-dimethylcyclohexane; trans-1,2-dimethylcyclohexane; cis-1,4-dimethylcyclohexane. after finding the most stable explain how this was found compared to the stability of all the other compounds.arrow_forwardMatch the following organic compounds with their correct pair.arrow_forward
- -Name the Ce Cyclohexanes from yesterday, include cis and trans. Powest in energy. - Decide which of the two conformers is - From all Go, decide CH3 CH3 Д b) CH3 CH3 CH3 6 1 CH3 5 ч CH3 CH3 CH3 по CH3 H₂C CH3 H₂ C CH3 which conformer is the lowest energy. CH3 З ру CH3 CH3 С CHE -СН3 CH3 CH3 ZH₂C CH3 пр CH3 HC Э н с CH3 CH3 CH3 С CH3 -CH3 CH3arrow_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_forwardWhich of the following compounds are trans-1-bromo-3-methylcyclohexane? A I and III B II and III C III and IV D I and IVarrow_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_forwardWrite a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.arrow_forwardWhich of the following molecules has the lowest strain energy? Cyclobutane Cyclopentane Cyclopropane Cyclohexanearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: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
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