Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 3, Problem 64P
Interpretation Introduction
Interpretation:
Check whether the trans-1,4-dimethylcyclohexane or cis-1-tertbutyl-3-methylcyclohexane will have a higher percentage of the diequatorial-substituted conformer compared with the diaxial-substituted conformer.
Concept introduction:
The axial substituent interferes with the axial hydrogens on C3 and C5 carbons. This interference generally called as 1, 3-diaxial interaction.
Considering,
Among this the equatorial isomer is more stable due to the absence of
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Which has a higher percentage of the diequatorial-substituted conformer compared with the diaxial-substituted conformer: trans-1,4-dimethylcyclohexane or cis-1-tert-butyl-3-methylcyclohexane?
Which has a higher percentage of the diequatorial-substituted conformer compared with the diaxial-substituted conformer: trans-1,4-difluorocyclohexane or cis-1-tert-butyl-3-
fluorocyclohexane?
O trans-1,4-difluorocyclohexane
O cis-1-tert-butyl-3-fluorocyclohexane
It is easy to imagine a cyclohexane as a flat hexagon and a lot of the time we draw it
that way. Looking at 1,3,5-triethylcyclohexane we cannot tell the stability of the
molecule from looking at the flat 2D drawing. Explain why we need to look at the 3D
configuration and what conformation (axial,equatorial) would each of the three ethyl
groups be in for the most stable configuration.
Chapter 3 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 3.1 - Name each of the following:Ch. 3.1 - Draw the structures and name the four...Ch. 3.1 - Draw the structure for each of the following...Ch. 3.1 - Name the following compounds:Ch. 3.1 - Prob. 7PCh. 3.2 - What is each compounds systematic name?Ch. 3.2 - Prob. 11PCh. 3.3 - Prob. 12PCh. 3.3 - Convert the following condensed structures into...Ch. 3.3 - The molecular formula for ethyl alcohol (CH3CH2OH)...
Ch. 3.3 - Draw a condensed and a skeletal structure for the...Ch. 3.3 - What is each compounds systematic name?Ch. 3.4 - Prob. 17PCh. 3.4 - Give two names for each of the following alkyl...Ch. 3.5 - Are the following compounds primary, secondary, or...Ch. 3.5 - Name the following amines and tell whether they...Ch. 3.5 - Draw the structures and provide systematic names...Ch. 3.6 - Predict the approximate size of the following bond...Ch. 3.7 - What is the smallest straight-chain alkane that is...Ch. 3.7 - Prob. 24PCh. 3.7 - Prob. 25PCh. 3.7 - Prob. 26PCh. 3.7 - List the compounds in each set from highest...Ch. 3.8 - Rank the following compounds in each set from most...Ch. 3.8 - In which solvent would cyclohexane have the lowest...Ch. 3.8 - Prob. 30PCh. 3.9 - Prob. 31PCh. 3.9 - a. Draw the three staggered conformations and the...Ch. 3.9 - a. Draw the most stable conformation of pentane...Ch. 3.11 - Draw 1,2,3,4,5,6-hexachlorocyclohexane with a. all...Ch. 3.12 - At any one time, would you expect there to be more...Ch. 3.13 - Prob. 36PCh. 3 - a. How many hydrogens does an alkane with 17...Ch. 3 - Prob. 2PCh. 3 - Draw a condensed structure and a skeletal...Ch. 3 - Prob. 39PCh. 3 - Prob. 40PCh. 3 - Which of the following represents a cis isomer?Ch. 3 - a. How many primary carbons does each of the...Ch. 3 - Name the following amines and tell whether they...Ch. 3 - Which of the following conformers of isobutyl...Ch. 3 - What is each compounds name? a. CH3CH2CH2OCH2CH3Ch. 3 - Draw the structural formula for an alkane that has...Ch. 3 - Which has a. the higher boiling point:...Ch. 3 - Ansaid and Motrin belong to the group of drugs...Ch. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 51PCh. 3 - Draw skeletal structures for the following: a....Ch. 3 - Prob. 53PCh. 3 - For rotation about the C-3 8 C-4 bond of...Ch. 3 - Prob. 55PCh. 3 - What is each compounds systematic name?Ch. 3 - Draw the two chair conformers for each of the...Ch. 3 - Draw the nine constitutional isomers with...Ch. 3 - Prob. 59PCh. 3 - Prob. 60PCh. 3 - Prob. 61PCh. 3 - Using Newman projections, draw the most stable...Ch. 3 - For each of the following disubstituted...Ch. 3 - Prob. 64PCh. 3 - Prob. 65PCh. 3 - What is each compounds systematic name?Ch. 3 - Prob. 67PCh. 3 - Bromine is a larger atom than chlorine, but the...Ch. 3 - Prob. 69PCh. 3 - Prob. 70PCh. 3 - a. Draw a potential energy diagram for rotation...
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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
- Why is a substituted cyclohexane ring more stable with a larger group in the equatorial position?arrow_forwardPlace the methyl groups by drawing the axial and equatorial positions on the cyclohexane structure in the chair conformations next to the cyclohexane derivatives named below.arrow_forwardThe energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).arrow_forward
- 5. Draw the two chair conformations ("ring filips") of trans –1- ethyl-4-methylcyclohexane to show the axial and equatorial substituents (including all hydrogens). Then determine which of the two conformations is more stable and why.arrow_forwardDraw all the possible conformations of trans- and cis-1,3-dimethylcyclobutane. Which of these conformations is the most stable conformation? Explain your answer. Discuss the type of strain(s) that affect the stability of these compounds.arrow_forwardcOH CH2OH H, ОН Н Ha ÓH H In its most stable chair conformation, indicate the orientation of each of the labeled groups in this substituted cyclohexane. Group a: equatorial Group b: axial Group c: equatorialarrow_forward
- Which of the following is a position isomer of 3-methylhex-2-ene? 2,3-dimethylpent-2-ene, 1,3-dimethylcyclopentane, isobutylcyclopropane, 3-methylhex-1-enearrow_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_forwardName 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_forward
- Write a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.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_forwardDraw the two chair conformations for each of the following compounds and indicate which conformer is more stable.arrow_forward
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