Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 3, Problem 3.51SP
The most stable form of the common sugar glucose contains a six-membered ring in the chair conformation with all the substituents equatorial. Draw this most stable conformation of glucose.
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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 structure for the most stable chair conformation of trans-1-isopropyl-3-methylcyclohexane.
Chapter 3 Solutions
Organic Chemistry (9th Edition)
Ch. 3.2 - Using the general molecular formula for alkanes:...Ch. 3.3B - Name the following alkanes and haloalkanes. When...Ch. 3.3B - Write structures for the following compounds. a....Ch. 3.3B - Provide IUPAC names for the following compounds....Ch. 3.3B - Prob. 3.5PCh. 3.3B - Prob. 3.6PCh. 3.3B - Prob. 3.7PCh. 3.3B - Draw the structures of the following compounds. a....Ch. 3.3B - Without looking at the structures, give molecular...Ch. 3.4C - Prob. 3.10P
Ch. 3.7B - Prob. 3.11PCh. 3.7C - Draw a graph similar to Figure 3-9, of the...Ch. 3.8B - Draw a graph similar to Figure 3-11, of the...Ch. 3.9 - Draw a perspective representation of the most...Ch. 3.10C - Give IUPAC names for the following compounds.Ch. 3.10C - Draw the structure and give the molecular formula...Ch. 3.11 - Which of the following cycloalkanes are capable of...Ch. 3.11 - Give IUPAC names for the following cycloalkanes.Ch. 3.12B - The heat of combustion of...Ch. 3.12C - Prob. 3.20PCh. 3.13B - The cyclohexane chair shown in Figure 3-22 has the...Ch. 3.13B - Draw 1,2,3,4,5,6-hexamethylcyclohexane with all...Ch. 3.14 - Prob. 3.23PCh. 3.14 - Prob. 3.24PCh. 3.14 - Draw the most stable conformation of a....Ch. 3.15 - Prob. 3.26PCh. 3.15 - a. Draw both chair conformations of cis-1...Ch. 3.15 - Prob. 3.28PCh. 3.15A - Draw the two chair conformations of each of the...Ch. 3.15B - Draw the most stable conformation of a....Ch. 3.16A - Name the following compounds.Ch. 3.16B - Prob. 3.32PCh. 3 - Prob. 3.33SPCh. 3 - Prob. 3.34SPCh. 3 - 3-35 a. Draw and name the five cycloalkane...Ch. 3 - Draw the structure that corresponds with each...Ch. 3 - Each of the following descriptions applies to more...Ch. 3 - Write structures for a homologous series of...Ch. 3 - Prob. 3.39SPCh. 3 - Construct a graph, similar to Figure 3-11, of the...Ch. 3 - The following names are all incorrect or...Ch. 3 - In each pair of compounds, which compound has the...Ch. 3 - There are eight different five-carbon alkyl...Ch. 3 - Use a Newman projection about the indicated bond...Ch. 3 - a. Draw the two chair conformations of...Ch. 3 - Draw the two chair conformations of each compound,...Ch. 3 - Using what you know about the conformational...Ch. 3 - Prob. 3.48SPCh. 3 - Draw Newman projections along the C3C4 bond to...Ch. 3 - Prob. 3.50SPCh. 3 - The most stable form of the common sugar glucose...Ch. 3 - This is a Newman projection of a substituted...
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- Consider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energyarrow_forwardFollowing is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4. (b) Which of these hydrogens are equatorial? Which are axial? (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?arrow_forwardFill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth methyl groups in __________ positions and one with both methyl groups in ____________ positions.arrow_forward
- Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this compound and state which of the two is more stable.arrow_forward6. The following compound exhibits two chair conformations. Draw them and indicate which one is more stable. Explain. H H -CH3 H3C H3C CH3arrow_forwardMenthol, a terpene, exists in a (1R,2S,5R) and(1S,2R,5S) form. Draw the two molecules in theirmost stable chair conformers (IUPAC name: 2-isopropyl-5-methylcyclohexanol).arrow_forward
- The most stable form of glucose (blood sugar) is a six-membered ring in a chair conformation with its five substituents all in equatorial positions. Draw the most stable conformer of glucose by putting the OH groups and hydrogens on the appropriate bonds in the structure on the right.arrow_forwardDraw the more stable chair conformation for the following compound. trans-1,2-dibutylcyclohexanearrow_forwardDraw the most stable chair conformation of trans-1,2-dimethylcyclohexane.arrow_forward
- Provide the most stable (lowest energy) chair conformation of methylcyclohexanearrow_forwardWhich of the following is the most stable conformation of the following compound? HO "CI CI HO. но. Но Он II IV 우arrow_forwardDraw 5 Chair Conformations of Cyclohexane with right side pointing up and 5 with the left side pointing up.arrow_forward
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