EBK ORGANIC CHEMISTRY
10th Edition
ISBN: 9781259636875
Author: Carey
Publisher: MCGRAW HILL BOOK COMPANY
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Chapter 3, Problem 30P
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 samemolecule, or are they stereoisomers that cannot be interconverted by rotation about single bonds? Which substituents (if any) occupy axial sites?
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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?
why is this the chair conformation for the cyclohexane? also is the chair conformation cis or trans
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Chapter 3 Solutions
EBK ORGANIC CHEMISTRY
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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- Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal for each one.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_forwardFollowing 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_forward
- Is 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_forwardPyrethrin II and pyrethrosin are two natural products isolated from plants of the chrysanthemum family. Pyrethrin II is a natural insecticide and is marketed as such. Q,) Label all chiral centers in each molecule and all carbon-carbon double bonds about which there is the possibility for cis,trans isomerism.arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?arrow_forward
- In the lowest energy chair conformation of cis-1,3-dimethylcyclohexane, how many axial positions are occupied by methyl groups?arrow_forwardIdentify the correct chair conformations of the following compound and then indicate which one is more stable.arrow_forwardWhich molecule would have their 2 chair conformations be of equal energies?arrow_forward
- According to the following structure, draw the Newmann projections in which you must indicate: a) the most stable conformation and explain why it is more stable, b) the least stable conformation and explain why; c) a conformation where there is a gauche interaction.arrow_forwardThe most stable conformation of the pyranose ring of most Daldohexosesplaces the largest group, CH2OH, in the equatorial position.An exception to this is the aldohexose D-idose. Draw the two possiblechair conformations of either the α or β anomer of D-idose. Explain whythe more stable conformation has the CH2OH group in the axial position .arrow_forwardChoose the two Newman chair conformations of ethylcyclohexane?arrow_forward
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