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 2.63P
On the left is a stereorepresentation of glucose (we discuss the structure and chemistry of glucose in Chapter 25).
- (a) Convert the stereorepresentation on the left to a planar hexagon representation.
- (b) Convert the stereorepresentation on the left to a chair conformation. Which substituent groups in the chair conformation are equatorial? Which are axial?
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Pertanyaan yang ada pada gambar
Draw the alternative chair conformations for the cis and
trans isomers of 1,2-dimethylcyclohexane, 1,3-
dimethylcyclohexane, and 1,4-dimethylcyclohexane. (a
) Indicate by a label whether each methyl group is axial
or equatorial. (b) For which isomer(s) are the alternative
chair conformations of equal stability? (c) For which
isomer(s) is one chair conformation more stable than
the other?
4. (a) Draw a skeletal (line-bond) structure for 3,4-dimethylhexane.
(b) Draw a sawhorse representation of any staggered conformation of this molecule looking down the
carbon-3 to carbon-4 bond.
(c) Draw a Newman projection looking down the carbon-3 to carbon-4 bond of the same conformation
that you drew as a sawhorse representation.
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 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_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_forwardConsider the following chair conformation of bromocyclohexane: H H H Br H H H (a) Identify whether the bromine atom occupies an axial position or an equatorial position in the conformation above. (b) Draw a bond-line drawing (skeletal structure) of this chair conformation (without Newman projections). (c) Draw a bond-line drawing of the other chair conformation (after a ring flip).arrow_forward
- Sight along the C2-C1 bond of 2-methylpropane (isobutane).(a) Draw a Newman projection of the most stable conformation.(b) Draw a Newman projection of the least stable conformation.(c) Make a graph of energy versus angle of rotation around the C2-C1 bond.(d) Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 4.0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.arrow_forwardDraw 2,4-dimethylhexane as a bond-line structure. Then, looking down the C3 – C4 bond, draw a Newman projection representation of the 1) lowest energy (most stable) and 2) highest energy (least stable) conformations.arrow_forward2.Using Newman projections, draw the most stable conformation for each of the following compounds. (a) 3-methyl pentane, viewed along the C2-C3 bond (b) 3,3-dimethyl hexane, viewed along the C3-C4 bondarrow_forward
- For 1,2-dichloroethane: (a) Draw Newman projections for all eclipsed conformations formed by rotation from 0 to 360° about the carbon-carbon single bond. (b) Which eclipsed conformation(s) has the lowest energy? Which has the highest energy? (c) Which, if any, of these eclipsed conformations are related by reflection?arrow_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(c)Conformational isomer is the different spatial arrangement of the atoms that resulted from rotation about a single bond. (i) Differentiate anti conformers and gauche conformers (ii) Using a newman projection, draw the anti conformer and gauche conformers of 3,3-dimethylheptane (viewed along the C3-C4 bond)arrow_forward
- Following is the Structural formal of Chloropropane H H H 2. H Draw Newman projections for all staggered and eclipsed conformation formed by rotation about C1 - C2 bond from 0° to 360°. b) Which Staggered conformation(s) has the lowest energy; which has the highest energy? c) Which eclipsed conformation(s) has the lowest energy, which has thhe highest energy?arrow_forward(2) Draw a more stable conformer of the following Newman Projection, and draw the skeletal structure. H Ø CH3 H H3C H Harrow_forward(a) Draw the most stable chair conformers of trans-1,3-diisopropylcyclohexane and trans-1,4-diisopropylcyclohexane. (b) Which is more stable: trans-1,3-diisopropylcyclohexane or trans-1,4-diisopropylcyclohexane?arrow_forward
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