Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 4.SE, Problem 23VC
Name the following compound, identify each substituent as axial or equatorial, and tell whether the conformation shown is the more stable or less stable chair form (green=Cl):
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Starting from the Newman projection below, rotate the back
carbon to provide the structure in the least stable
conformation.
(H3C)₂HC H
Q
IX
H^
H
H
CH3
o
For trans‑1‑ethyl‑4‑isopropylcyclohexane, which structures represent the possible boat conformations?
NH2
Br
1 OH
ОН
(a) Use the template below and drawa Newman projection for this conformation of the compound when viewed along the C2-C3
bond.
CH2OH
(b) Why is this the most stable conformation?
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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- Draw the most stable conformation of 1,4-dichlorobutane, using wedges and dashes to represent bonds coming out of the paper and going behind the paper, respectively.arrow_forwardFollowing 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_forwardPrautice qt#12 For the following compound, draw the appropriate Newman projection along the C1-C2 bond of the following: HE Су a) The most stable conformer and name the conformer. b) The least stable conformer and name the conformer. c) The second most stable conformer and name the conformer.arrow_forward
- Which staggered conformation(s) has (have) the lowest energy? Which has (have) the highest energy?arrow_forwardAcetylcholine is a neurotransmitter in the central nervous system in humans. Sighting along the C - C bond, draw Newman projection formulas for the anti and gauche conformations of acetylcholine.arrow_forwardAcetylcholine is a neurotransmitter in the central nervous system in humans. Sighting along the C-C bond, draw Newman projection formulas for all the eclipsed and staggered conformers of acetylcholine. Which among the conformers is the least stable? The most stable? Plot a conformational analysis for these conformers.arrow_forward
- Are the C¬C bonds cyclopropane weaker than those in cyclohexane?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. H,C CH3 H H H CH3arrow_forwardBuild a model (attach a photo) of the following Newman projection viewed along the C2→C3 bond. Draw a line structure of the most stable conformation with the -CH2OH on the left hand side: 1.2 H HO Br- 'Bu CH,OH 1arrow_forward
- Consider the substituted cyclohexane shown in the ball-and-stick model. (See attached) Draw the second possible conformation in the chair form, and classifyit as more stable or less stable than the conformation shown in thethree-dimensional model ?arrow_forwardCalculate the number of degrees of unsaturation for each molecular formula, and propose two possible structures: (a) C8H12; (b) C10H10.arrow_forwardNonearrow_forward
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