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Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 2.6, Problem AQ
Interpretation Introduction
Interpretation:
The relationship between the boxed atom and the circled atoms in the given structure has to be given.
Concept Introduction:
Cis, Trans Isomerism in Bicycloalkanes:
Depending on the orientation of two hydrogen atoms at the ring junction, whether the hydrogens are cis or trans to each other, two stereoisomers are possible for bicycloalkanes.
Example: Decalin:
Figure 1
Since both the ring in bicycloalkane is locked into one chair conformation, neither ring can invert to its alternative chair and thus the other substituent on ring which would be in equatorial position will remian equatorial and the substituent which would be in axial position will remain axial.
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Provide an appropriate word which may
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Chapter 2 Solutions
Organic Chemistry
Ch. 2.2 - Do the line-angle formulas in each pair represent...Ch. 2.2 - Draw line-angle formulas for the three...Ch. 2.3 - Write IUPAC names for these alkanes.Ch. 2.4 - Combine the proper prefix, infix, and suffix and...Ch. 2.4 - Write the molecular formula, IUPAC name, and...Ch. 2.4 - Write molecular formulas for each bicycloalkane,...Ch. 2.4 - Prob. 2.7PCh. 2.5 - For 1,2-dichloroethane: (a) Draw Newman...Ch. 2.5 - Following is a chair conformation of cyclohexane...Ch. 2.5 - Draw the alternative chair conformation for the...
Ch. 2.5 - Draw a chair conformation of...Ch. 2.6 - Which cycloalkanes show cis, trans isomerism? For...Ch. 2.6 - Following is a planar hexagon representation for...Ch. 2.6 - Here is one cis,trans isomer of...Ch. 2.6 - Prob. AQCh. 2.6 - Prob. BQCh. 2.6 - Prob. CQCh. 2.7 - Arrange the alkanes in each set in order of...Ch. 2 - Write a line-angle formula for each condensed...Ch. 2 - Write the molecular formula of each alkane.Ch. 2 - Using parentheses and subscripts, provide an even...Ch. 2 - Which statements are true about constitutional...Ch. 2 - Prob. 2.20PCh. 2 - Each member of the following set of compounds is...Ch. 2 - Each of the following compounds is an amine...Ch. 2 - Each of the following compounds is either an...Ch. 2 - Draw structural formulas and write IUPAC names for...Ch. 2 - Draw structural formulas for all of the following....Ch. 2 - Write IUPAC names for these alkanes and...Ch. 2 - Write structural formulas and line-angle formulas...Ch. 2 - Explain why each is an incorrect IUPAC name and...Ch. 2 - For each IUPAC name, draw the corresponding...Ch. 2 - Write the IUPAC name for each compound.Ch. 2 - Prob. 2.31PCh. 2 - Torsional strain resulting from eclipsed CH bonds...Ch. 2 - How many different staggered conformations are...Ch. 2 - Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a...Ch. 2 - Consider 1-bromo-2-methylpropane and draw the...Ch. 2 - trans-1,4-Di-tert-butylcyclohexane exists in a...Ch. 2 - From studies of the dipole moment of...Ch. 2 - Prob. 2.38PCh. 2 - Following are the alternative chair conformations...Ch. 2 - Prob. 2.40PCh. 2 - Prob. 2.41PCh. 2 - Draw line-angle formulas for the cis and trans...Ch. 2 - Name and draw structural formulas for all...Ch. 2 - Using a planar pentagon representation for the...Ch. 2 - Gibbs free energy differences between...Ch. 2 - Prob. 2.46PCh. 2 - Calculate the difference in Gibbs free energy in...Ch. 2 - Draw the alternative chair conformations for the...Ch. 2 - Use your answers from Problem 2.48 to complete the...Ch. 2 - There are four cis,trans isomers of...Ch. 2 - Draw alternative chair conformations for each...Ch. 2 - 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans...Ch. 2 - Prob. 2.53PCh. 2 - What generalization can you make about the...Ch. 2 - What unbranched alkane has about the same boiling...Ch. 2 - Complete and balance the following combustion...Ch. 2 - Following are heats of combustion per mole for...Ch. 2 - Following are structural formulas and heats of...Ch. 2 - Without consulting tables, arrange these compounds...Ch. 2 - Which would you predict to have the larger (more...Ch. 2 - Following are structural formulas for 1,4-dioxane...Ch. 2 - Following is a planar hexagon representation of...Ch. 2 - On the left is a stereorepresentation of glucose...Ch. 2 - Prob. 2.64PCh. 2 - Prob. 2.65P
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- cis-1,2-Dimethylcyclohexane is optically inactive even though it has two chirality centers. Explain.arrow_forwardWat are the four alcohols with the molecular formula C4H9OH. How many of these are chiral?arrow_forwardThe chiral compound of the following is: 1- trans-1,3-dichlorocyclobutane II- trans-1,2-dichlorocyclobutane IV- cis-1,3-dichlorocyclobutane Il- cis-1,2-dichlorocyclobutane O II O II O IV O None of the abovearrow_forward
- Draw the chair conformation for the lowest energy conformationarrow_forwardIs cis-1,2-dibromocyclohexane a meso compound? In its planar structure, it has a line of symmetry but it has two chiral carbons. However, in its chair conformation, it does not look like it has a line of symmetry but it has two chiral carbons.arrow_forwardCompare the two possible chair conformations of this molecule. Given the AG for the two possible chair conformations, calculate the equilibrium constant for the interconversion between the two chair conformers at room temperature. CI H3C AG = 1.3 kcal/mol %3D AG = -RT In K %3D rearranges to K = e-AG/RT %3D R = 1.987 x 10-3 kcal/molK ||arrow_forward
- Following are the alternative chair conformations for trans-1,2-dimethylcyclohexane.(a) Estimate the difference in free energy between these two conformations.(b) Given your value in (a), calculate the percent of each chair present in anequilibrium mixture of the two at 25°C.arrow_forwardOne of the isomers of 1,2,3,4,5,6-hexahydroxycyclohexane, called myo-Inositol, acts as a growth factor in both animals and microorganisms. Draw the most stable chair conformation of myo-Inositol (Note: account the wedge and dash projection). Draw the most stable cis-trans stereoisomer of myo-Inositol. OH HO ОН HO "OH ОНarrow_forwardClassify the folowing pair of molecules as enantimoers or diastereomersarrow_forward
- How many stereocentres are there in quinine, an antimalarial drug? What is the maximum number of stereoisomers possible for this molecule? N "OH quininearrow_forwardProvide the most stable (lowest energy) chair conformation of methylcyclohexanearrow_forwardDescribe the conformation of rings A, B, C, and D in cholestanol.arrow_forward
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