ORGANIC CHEMISTRY

5th Edition

ISBN: 9781259977596

Author: SMITH

Publisher: MCG

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Textbook Question

Chapter 4, Problem 4.65P

Hydrocarbons like benzene are metabolized in the body to arene oxides, which rearrange to form

phenols. This is an example of a general process in the body, in which an unwanted compound

(benzene) is converted to a more water-soluble derivative called a metabolite, so that it can be

excreted more readily from the body.

Chapter 4, Problem 4.65P, 4.65 Hydrocarbons like benzene are metabolized in the body to arene oxides, which rearrange to form

a. Classify each of these reactions as oxidation, reduction, or neither.

b. Explain why phenol is more water soluble than benzene. This means that phenol dissolves in urine, which is largely water, to a greater extent than benzene.

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Chapter 4, Problem 4.64P

Chapter 4, Problem 4.66P

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Chapter 4 Solutions

ORGANIC CHEMISTRY

Ch. 4 - Prob. 4.1P Ch. 4 - Problem 4.2 Which of the following is not another...Ch. 4 - Problem 4.3 Draw the five constitutional isomers...Ch. 4 - Prob. 4.4P Ch. 4 - Prob. 4.5P Ch. 4 - Draw the five constitutional isomers that have...Ch. 4 - Problem 4.7 Give the IUPAC name for each...Ch. 4 - Give the IUPAC name for each compound. a....Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.10P

Ch. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.15P Ch. 4 - Prob. 4.16P Ch. 4 - Problem 4.17 a. Draw the three staggered and...Ch. 4 - Problem 4.18 Rank the following conformations in...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Problem 4.24 Draw both conformations for and...Ch. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.27P Ch. 4 - Problem 4.28 Consider . Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.30P Ch. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.33P Ch. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.36P Ch. 4 - Prob. 4.37P Ch. 4 - 4.38 Give the IUPAC name for each compound. a. c....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 - 4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.41P Ch. 4 - 4.42 Give the IUPAC name for each compound. a....Ch. 4 - Prob. 4.43P Ch. 4 - Prob. 4.44P Ch. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - 4.46 Considering rotation around the bond...Ch. 4 - Prob. 4.47P Ch. 4 - 4.48 (a) Using Newman projections, draw all...Ch. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.57P Ch. 4 - Prob. 4.58P Ch. 4 - 4.59 Classify each pair of compounds as...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.61P Ch. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.63P Ch. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 4.66P Ch. 4 - Prob. 4.67P Ch. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.69P Ch. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.71P Ch. 4 - Prob. 4.72P Ch. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...

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Solution Summary: The author explains that phenol is more water soluble than benzene.

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