ORGANIC CHEMISTRY-EBOOK>I<
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ISBN: 9781305084414
Author: McMurry
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Chapter 4.SE, Problem 61AP
Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal for each one.
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Chapter 4 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
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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- Gibbs free energy differences between axial-substituted and equatorial-substituted chair conformations of cyclohexane were given in Table 2.4. (a) Calculate the ratio of equatorial to axial tert-butylcyclohexane at 25C. (b) Explain why the conformational equilibria for methyl, ethyl, and isopropyl substituents are comparable but the conformational equilibrium for tert-butylcyclohexane lies considerably farther toward the equatorial conformation.arrow_forwardConsider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energyarrow_forwardName and draw structural formulas for the eight constitutional isomeric alcohols with molecular formula C5H12O. Classify each alcohol as primary, secondary, or tertiary. Which are chiral?arrow_forward
- Select the more stable conformation overall. D A.arrow_forwardMake a model of each compound, draw it in its most symmetric conformation, and determine whether it is capable of showing optical activity. trans-1,4-dibromocyclohexanearrow_forward2 1 Group activity: Use molecular model to convert the given 3D perspective structure to Newman projection around C-C bond on the template provided. Fill in the substituent for the most stable conformation in the templates provided. H H OH Br OH CH Y/ 3D of most stable conformation ΕΙ Fischer projection of most stable conformation most stable conformation Use the molecular model of chair conformation of cyclohexane and fill in the substituents in the template provided for chair conformation and complete the Newman projections showing only substituents for given molecules. Circle the chair conformation which is more stable. 1) cis-3-isopropylcyclohexanol 2) trans-3-Isopropylcyclohexaol QOarrow_forward
- Below are isomers of tert-butylcyclohexanol in conformational structures. Two are cis-2-tert- butylcyclohexanol and two are cis-3-tert-butylcyclohexanol. Indicate which is the more stable conformation for each pair, and indicate which of all four conformations is the most stable. A OH Ex HO B D OH OHarrow_forwardDraw a structural formula for the major organic product of the following reaction: CI- 유 CH2Cl2 CH=CHCOH + Cl2 ⚫ Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. • If enantiomers are formed, just draw one.arrow_forwardDraw the structure(s) of the cycloalkanes with molecular formula C6H12 that have a 3-membered ring and two substituents.arrow_forward
- Draw the most stable conformers of trans-1-Bromo-4-methylcyclohexane and cis-1-Bromo-4-methylcyclohexane. Which is more stable? Explain the reason for your answer.arrow_forwardDraw a structural formula for the alkene you would use to prepare the alcohol shown by hydroboration/oxidation. -CHCH3 ОН • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forwardDraw a structural formula for the alkene you would use to prepare the alcohol shown by hydroboration/oxidation. H3C CH3 CH3CHCCH3 ОН You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
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