Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 4.8, Problem 19P
Identify each substituent in the following compound 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
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?
Identify the cyclohexane chair conformation with an axial ethyl substituent and equatorial
methyl group.
OL
O II
III
O IV
C
>
။
IV
Chapter 4 Solutions
Organic Chemistry
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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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 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_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_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_forward
- H3C HC 10 aH CH3 In its most stable chair conformation, indicate the orientation of each of the labeled groups in this substituted cyclohexane. Group a: Group b: Group c:arrow_forwardDraw the most stable conformation of the disubstituted cyclohexane below.arrow_forwardDraw the lowest energy conformation of the following molecule along C2-C3. : OH 3 : ОНarrow_forward
- H C-Ć- C -CI Following is the structural formula of 1,2– dichloroethane. H H a) Draw Newman projections for all staggered and eclipsed conformations formed by rotation from 0° to 360° about the carbon- carbon single bond. 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 the highest energy?arrow_forwardWhich staggered conformation(s) has (have) the lowest energy? Which has (have) the highest energy?arrow_forward5) For the following: a) Draw the "flat" line structure of the following (be sure to indicate stereochemistry) Br OH b) Draw both chair conformations of the following compound. Indicate which form is the most stable H3C°arrow_forward
- Starting from the wedge-and-dash structure below, rotate the back carbon to provide the Newman projection in the least stable conformation. HO H H H aarrow_forwardThe sp3 orbitals of carbon in CH4 are formed from the three 2p orbitals. 2s and two of the 2p orbitals. 2s and one of the 2p orbitals. 2s and the three 2p orbitals.arrow_forwarddraw 2 cyclohexane conformationsarrow_forward
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