Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 3.12, Problem 13P
Write structural formulas for the most stable conformation of each of the following compounds:
(a) trans-
(b) cis-
(c) trans-
(d) cis-
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Students have asked these similar questions
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?
Write the two chair conformations of each of the following and in each part designate whichconformation would be the more stable: (a) cis-1-tert-butyl-3-methylcyclohexane, (b) trans-1-tert-butyl-3-methylcyclohexane, (c) trans-1-tert-butyl-4-methylcyclohexane, ( d) cis-1-tert-butyl-4-methylcyclohexane.
Draw the most stable conformation of(a) trans-1-tert-butyl-3-(1,1-dimethylpropyl)cyclohexane.
Chapter 3 Solutions
Organic Chemistry - Standalone book
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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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
- 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_forwardThere are four cis,trans isomers of 2-isopropyl-5-methylcyclohexanol:(a) Using a planar hexagon representation for the cyclohexane ring, draw structural formulas for the four cis,trans isomers.(b) Draw the more stable chair conformation for each of your answers in part (a).(c) Of the four cis,trans isomers, which is most stable? (Hint: If you answered thispart correctly, you picked the isomer found in nature and given the name menthol.)arrow_forwardCH3 Flo A CH3 CH3 D B A E F DC C D CH3 H3C- CH 3 B E CH3 H3C 1 CH₂ H H3C C CH3 CH3 F For cis-1,3-dimethylcyclohexane, which two chair conformations are in equilibrium?arrow_forward
- Given the structures of the following two tetramethylcyclohexanes: CH3 CH3 H3C" CH3 H3C" CH3 CH3 CH3 A B (a) Draw the most stable chair conformation for both A and B. Which structure is lower in energy (most stable)? (b) Ring flip the above structures and draw the least stable chair conformation for both A and B. Which structure is highest in energy (least stable)?arrow_forward4.For each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformations would be both equatorial in one chair conformer and both axial in the other, or one equatorial and one axial in each of the two chair conformers. (a) Cis-1,2- (b) Trans-1,2- (c) Cis-1,3- (d) Trans-1,3- (e) Cis-1,4- (f) Trans-1,4-arrow_forwardDraw the most stable conformation of cis-1-tert-butyl-3-ethylcyclohexane. (a) (b) trans-1-tert-butyl-2-methylcyclohexane. (c) trans-1-tert-butyl-3-(1,1-dimethylpropyl)cyclohexane.arrow_forward
- Following are the alternative chair conformations for trans-1,2-dimethylcyclohexane.(a) Estimate the difference in free energy between these two conformations.(b) Given your value in (a), calculate the percent of each chair present in anequilibrium mixture of the two at 25°C.arrow_forwardDraw a chair conformer and the ring-flipped conformed and determine which conformer for each pair you drew in part(a) is more stable. (i) 1-tert-butyl-1-methylcyclohexane (ii) cis-1-tert-butyl-3-methylcyclohexanearrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?arrow_forward
- Which of the following disubstituted cyclohexanes could exist in a conformation that has both groups equatorial (a) cis-1,3-dimethylcyclohexane(b) cis-1,4-dimethylcyclohexane(c) trans-1,3-dimethylcyclohexane(d) cis-1,2-dimethylcyclohexanearrow_forwardIdentify the most stable conformation for 1 tert-butyl-3-methlyclohexanearrow_forwardwhat is the most stable conformation of (1R, 2S, 5R)-1,2,5-trimethylcyclohexanearrow_forward
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