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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Cyclohexane 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.
11.
s) Draw the most stable conformation of 1,3-dichloro-2,4-difluorocyclohexane:
12. Which of the following represents the most stable conformation of 1,2,4,5-
tetramethyleyclohexane? (one correct answer)
CH
b)
CH
HC
H-
H-
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HC
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6.
Give IUPAC name for the following molecule. Include "cis" and "trans"
designations if applicable.
H2C-CH3
H
-CH2
H-
H
Br
The general values for steric and torsional strain are provided. Use
these values to calculate the difference in energy between the two
conformations of 2-methylbutane in the box.
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3.8
Heigned bond
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Question 71 of 100
CH₂CH₂
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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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- 5. Draw the two chair conformations ("ring filips") of trans –1- ethyl-4-methylcyclohexane to show the axial and equatorial substituents (including all hydrogens). Then determine which of the two conformations is more stable and why.arrow_forwardन A 8-£ Barrow_forwardDraw the most stable structure of cis-1-tbutyl-2-methylcyclohexane. Your structure should clearly distinguish between axial and equatorial positions.arrow_forward
- Please explain in detail about these topics along with the structurearrow_forward10. One cis, trans isomer of 3,5-dimethylcyclohexanol is drawn below (left). Complete the drawings of the alternative chair conformations of this molecule (right), adding methyl substituents in axial and/or equatorial positions, as appropriate. Circle the more stable conformation. H3C,,, ОН OH -ОН CH3arrow_forward11. Which one of these forms of 1,2,4-trimethylcyclohexane can have a chair conformation in which the methyl groups are all equatorial? III ++ |||| A B с D Earrow_forward
- Draw all Newman projections of 2,2 bromopropane conformations in which the CH3 group and the H of the CHY2 group are positioned 'gauche' to each other.arrow_forwardWhich will be more stable, cis or trans-1,4-tert-butylcyclohexane? Explain by drawing their structures?arrow_forward7. Which one of the following conformations of disubstituted cyclohexanes is expected to be the most stable? H,C CH, - CH3 A) B) CH3 CH3 CH, D) CH, CH, OB ODarrow_forward
- Consider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?arrow_forwardH2. Please explain with details also explain wrong optionsarrow_forwardProvide an IUPAC name for each of the compounds shown. (Specify (E)/(Z) stereochemistry, if relevant, for straight chain alkenes only. Pay attention to commas, dashes, etc.) C=C CHCH(CH3)2 ČH3 3,4-dimethylpent-1-ene ÇH3 CH3 YCH3 CH3CHC CH3 H CH3 |2,2,4,5-tetramethylhex-2-ene An error has been detected in your answer. Check for typos, miscalculations etc. before submitting your answer.arrow_forward
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