Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 4.7, Problem 17P
Look at Figure 4-12 on page 105, and estimate the percentages of axial and equatorial conformations present at equilibrium in bromocyclohexane.
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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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- From the data in Figure 4-12 and Table 4-1, estimate the percentages of molecules that have their substituents in an axial orientation for the following compounds: (a) Isopropylcyclohexane (b) Fluorocyclohexane (c) Cyclohexanecarbonitrile, C6H11CNarrow_forwardPlease draw the line structures of all of the C8H17+ carbocations that have the carbon-skeleton below. And circle the most stable carbocation of those drawn.arrow_forwardWhich of the described conformations of trans-1-isopropyl-3-methylcyclohexane will be the most stable? Select one: a. The one in which both groups are equatorial b. The one in which the isopropyl group is axial and methyl group is equatorial c. The one in which the twist boat conformation is adopted d. The one in which the methyl group is axial and the isopropyl group is equatorial e. The one in which two substituents (groups) are axialarrow_forward
- Consider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?arrow_forwardhow can i rank these isomers from lowest bp to highest please? Trans-pent-2-ene Cis-pent-2-ene 3-methylbut-1-ene 2-methylbut-1-ene 2-methylbut-2-ene Cyclopentane Methylcyclobutane Ethylcyclopropane 1,2-dimethylcyclopropane 1,1-dimethylcyclopropane (don't answer only, need explaination)arrow_forwardhow can i rank these isomers from lowest bp to highest please? Trans-pent-2-ene Cis-pent-2-ene 3-methylbut-1-ene 2-methylbut-1-ene 2-methylbut-2-ene Cyclopentane Methylcyclobutane Ethylcyclopropane 1,2-dimethylcyclopropane 1,1-dimethylcyclopropanearrow_forward
- Increased substitution around a bond leads to increased strain. Take the four substituted butanes listed below, for example. For each compound, sight along the C2-C3 bond and draw Newman projections of the most stable and least stable conformations. Use the data in Table 3-5 to assign strain-energy values to each conformation. Which of the eight conformations is most strained? Which is least strained? (a) 2-Methylbutane (b) 2,2-Dimethylbutane (c) 2,3-Dimethylbutane (d) 2,2,3-Trimethylbutanearrow_forwardConsider the molecule 1-bromo-2-methylbutane. C3 and C4 should be drawn as Et as in theexample. This group is called an ethyl group and can be considered a sphere about twice the sizeof a methyl group. Draw the following Newman projections sighting down the C1C2 bond... a. The lowest potential energy conformation. b. The highest potential energy staggered conformation.arrow_forwardCyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq.arrow_forward
- Construct a qualitative potential energy diagram for rotation about C-C bond of 1,2-dibromoethan. Which conformation would you expect to be more stable? label the anti and gauche conformation of 1,2-dibromoethanearrow_forwardusing newman projections draw the least and most stable conformations with respect to the bond indicated 1-hexyne (C3 is front carbon and C4 is back carbon)arrow_forwardTrue or False (give true answer) - 2-methylpropene produces the more stable carbocation than but-2-ene. - When 1-methylcyclopentene undergoes an addition reaction with a carbocation intermediate, the carbocation will form on Carbon 5. - 3,3-diethylhex-1-ene will undergo rearrangement upon formation of a carbocation. - 3-methylcyclopentene will undergo rearrangement upon formation of a carbocation. - 1-ethylcyclopent-1-ene is the name of the product of reaction of 1-bromo-2-ethylcyclopentane with KOH in ethanol solventarrow_forward
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