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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Textbook Question
Chapter 2, Problem 2.62P
Following is a planar hexagon representation of L-fucose, a sugar component of the determinants of the A, B, O blood group typing. For more on this system of blood typing, see “Chemical Connections: A, B, AB, and O Blood Group Substances” in Chapter 25.
- (a) Draw the alternative chair conformations of L-fucose.
- (b) Which of them is more stable? Explain.
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2.
Identify the type of stereoisomerism in each of the following molecules and draw the
stereoisomer pair.
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(b)
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The following are representations of two forms of glucose. The six-membered ring is known to exist in a chair conformation in each form. Draw clear representations of the most stable conformation of each. Are they two different conformations of the same molecule, or are they stereoisomers that cannot be interconverted by rotation about single bonds? Which substituents (if any) occupy axial sites?
draw the most stable conformation of
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(b) 3-isopropyl-1,1-dimethylcyclohexane
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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- 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_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?arrow_forward(B) Draw two chair conformations of the following substituted cyclohexane and identify the most stable conformation. Clearly show the axial and equatorial bonds.arrow_forward
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