Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Question
Chapter 3, Problem 27P
Interpretation Introduction
Interpretation:
Whether the two structures in each of the given pairs represent constitutional isomers, different conformations of the same compound, or stereoisomers that cannot be interconverted by rotation about single bonds is to be determined.
Concept introduction:
Different compounds having same molecular formula are called isomers. They can either differ in connectivity or differ in the arrangement of atoms in space.
Different spatial arrangements of a molecule are made by rotation about single bonds. These structures are called as conformations, that is., structures can be made identical by rotation around one or more single bonds.
Stereoisomers have the same constitution but they have different special arrangement of atoms.
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Students have asked these similar questions
Which of the following is an incorrect statement:
Isomers have the same molecular formula such as cyclohexane and 1-hexene.
Conformational isomers are enantiomers or diastereomers, which can interconvert through rotations around bonds within molecules, which include anti and gauche
butane.
Stereoisomers have the same connectivity but different arrangement of their parts in space, which include enantiomers, diastereomer, and conformational isomers,
which include cis and trans dichlorocyclobutane.
O Structural or constitutional isomers are molecules of the same formula but different connectivity such as 1,1-dichlorocyclopropane and 1.2-dichlorocyclobutane.
Draw the two chair conformations for each of the following compounds and indicate which conformer is more stable.
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
Organic Chemistry - Standalone book
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
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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
- Indicate the relationship between the two structures in the pair. Are they chair conformations of the same molecule? If so, are they conformational diastereomers, conformational enantiomers, or identical? If they are not conformations of the same molecule, what is their stereochemical relationship? CH₂ CH₂ H₂C H₂C CH₂ Which statement is true? Ho CH₂ They are chair conformations of the same molecule, and they are conformational enantiomers. They are different molecules, and they are enantiomers. They are different molecules, and they are diastereomers. They are identical conformations of the same molecule. They are chair conformations of the same molecule, and they are conformational diastereomers.arrow_forwardHow To Draw the Two Conformations for a Substituted Cyclohexane ?arrow_forwardDraw six isomeric cyclopentanes of molecular formula C7H14. These will include four constitutional isomers, of which two show geometric (cis-trans) stereoisomerism.arrow_forward
- Place 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_forwardWrite the energy diagram corresponding to each conformer by writing the conformers (and Newman projection formulas) formed by the rotation of the bond between the carbon 3 and 4 (C3 and C4) of the 2-methylpentane. Indicate the most stable and unstable conformers.arrow_forwardIdentify the correct chair conformations of the following compound and then indicate which one is more stable.arrow_forward
- Rank the conformations of n-butane with reference to its potential energy from the most stable to the least stable. Rank from the most stable to the least stable.To rank items as equivalent, overlap them.arrow_forwardIndicate whether the pair of structures shown represent stereoisomers, constitutional isomers, different conformations of the same compound, or the same conformation of a compound view from a different perspective. Note that cis, trans isomers are an example of stereoisomers. Br H3C- Br Br OCH3 H3C Br OCH3 stereoisomers constitutional isomers different conformations same conformation.arrow_forward4. Which of the following statements is a correct description of the most stable chair conformation of 1,1,3-trimethylcyclohexane? Show structures to explain your answer a) The methyl group at C-3 is equatorial. b) C-1 is a tertiary carbon and C-3 is a primary carbon. c) C-1 is a quaternary carbon and C-3 is a secondary carbon. d) C-1 is a tertiary carbon and C-3 is a secondary carbon. e) Both methyl groups at C-1 are equatorial.arrow_forward
- Tell whether the following pairs of compounds are identical, constitutional isomers, stereoisomers, or unrelated. (a) cis-1, 3-Dibromocyclohexane and trans-1, 4-dibromocyclohexane (b) 2, 3-Dimethylhexane and 2, 3, 3-trimethy1pentanearrow_forwardIndicate whether the members of each of the following pairs of hydrocarbons are (1) constitutional isomers, (2) stereoisomers, or (3) not isomers. a. 2-Methylpentane and cyclopentane b. 2-Methylpentane and 2-ethylpentane c. Ethylcyclohexane and 1,2-dimethylcyclohexane d. cis-l,3-Diethylcyclobutane and trans-1,3-diethylcyclobutanearrow_forwardThere are 17 possible alkene isomers with the formula C6H12. Draw structures of the five isomers in which the longest chain has six carbon atoms, and give the name of each. Are any of these isomers chiral? (There are also eight isomers in which the longest chain has five carbon atoms, and four isomers in which the longest chain has four carbon atoms. How many can you find?)arrow_forward
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