Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 4.SE, Problem 58AP
Tell whether each of the following substituents on a steroid is axial or equatorial. (A substituent that is “up” is on the top face of the molecule as drawn, and a substituent that is “down” is on the bottom face.)
(a) Substituent up at C3
(b) Substituent down at C7
(c) Substituent down at C11
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(v) Identify every chiral center in cholesterol (below) with an asterisk.
HO
(vi) Draw an energy vs. dihedral angle diagram that represents all the conformations of butane
starting from the anti-conformation.
(vii) Draw both chair conformations for the compound shown below using the templates provided.
Circle the chair conformation that is lowest in energy.
Br
(viii) Draw a chair conformation that meets the following criteria.
Axial chlorine at C5
Equatorial methyl at C4
Bromine on C2 that is cis to the chlorine
6
2
5
3
4
) NH₂
For the questions below, more than one answer may be correct.
Circle all of the correct answers regarding the following compounds.
Br
Br
A
Br
B
Br
(a) Which pair of compounds are identical?
(b) Which pair of compounds are enantiomers?
(c) Which pair of compounds are diastereomers?
(d) Which compounds are chiral?
(e) Which compounds are meso?
C
Br
Br
D
AB AC AD BC BD CD none
AB AC AD BC BD CD none
AB AC AD BC BD CD none
ABCD none
A B C D none
5
a) Sighting down the C3-C4 bond, draw the gauche (60 degrees) and anti (180 degrees) Newman projections of 2,4-dimethylhexane.
b) Circle the conformation that you drew that is lower energy.
Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
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- You have isolated a new trisaccharide from a new species of insect shown below that you are calling Jiminy-Cricketose. Draw the Hayworth Projection of the molecule to the right of it. НО,, НО НО НО ОН OH ОН ОН "ОН ОН ОНarrow_forwarda) Draw the following compound in topological structure (zig-zag) and name the conformation that is drawn: b) Determine if each of the following molecules is an enantiomer, a diastereoisomer, an isomer in constitution or identical to the molecule in (a) and which is drawn in the box. Solve all parts otherwise I will downvotearrow_forward4. (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.arrow_forward
- Give answer to all parts otherwise i will give you downwardarrow_forward3) a) Using Newman projections, draw the lowest and highest energy conformers of 2- methylbutane, with respect to rotation around the C2-C3 bond. b) What is the barrier to rotation (difference in energy between lowest and highest) around the C2-C3 bond of 2-methylbutane?arrow_forwardI NEED HELP WITH BOTH QUESTIOND PLEASEarrow_forward
- Question attachedarrow_forward5) Draw the chair conformer described in (a), adding only the substituents (not the hydrogen groups of those stereocenters) onto the template below. a) Br CH3 Ph Complete the table, indicating how many of each type of interaction is present in total for the chair conformer described in (a). gauche interactions between gauche interactions substituents and the ring 1,3-diaxial between substituents interactions between substituents Draw the other conformer that results from a chair flip onto the template below. Make he changes that happen in the chair flip, but don't make other changes. Only draw substituents.arrow_forwardHelparrow_forward
- 3. Determine whether the following statements are true or false. Completely fill in the circle in front of your chosen answer. (a) A compound with a plane of symmetry must be achiral. (b) A compound with two or more stereocenters must be chiral. (a) O True O False True O Falsearrow_forwarda) Draw the least favorable conformation of 2,3,4-trimethylpentane along the C2-C3 axis in a Sawhorse projection. b) Draw the most favorable conformation of 2,3,4-trimethylpentane along the C2-C3 axis in a Newman projection.arrow_forward5) Which of the following statements describes the compound shown below? F A) It is achiral. B) The mirror image of this molecule is its diastereomer. C) Its asymmetric center possesses the R configuration. D) It is meso.arrow_forward
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