Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 8.SE, Problem 23VC
Interpretation Introduction
a)
Interpretation:
The structures of
Concept introduction:
The hydroboration reaction takes place with syn stereochemistry and results in a non-Markovnikov addition of water to the double bond in the alkene. The resulting product has the hydroxyl group on the carbon with less number of alkyl substitutents.
The oxymercuration-demercuration reaction takes place with anti stereochemistry and results in Markovnokov addition of water to the double bond in the alkene. The resulting product has the hydroxyl group on the carbon with more number of alkyl substitutents.
To give:
The structures of alkenes that would yield the alcohol shown on hydration.
To state:
Among hydroboration-oxidation and oxymercuration-demercuration methods which method can be used to prepare the alcohol from alkenes.
Interpretation Introduction
b)
Interpretation:
The structures of alkenes that would yield the alcohol shown on hydration are to be given. Among hydroboration-oxidation and oxymercuration-demercuration, the method which can be used to prepare the alcohol also has to be stated.
Concept introduction:
The hydroboration reaction takes place with syn stereochemistry and results in a non-Markovnikov addition of water to the double bond in the alkene. The resulting product has the hydroxyl group on the carbon with less number of alkyl substitutents.
The oxymercuration-demercuration reaction takes place with anti stereochemistry and results in Markovnokov addition of water to the double bond in the alkene. The resulting product has the hydroxyl group on the carbon with more number of alkyl substitutents.
To give:
The structures of alkenes that would yield the alcohol shown on hydration.
To state:
Among hydroboration-oxidation and oxymercuration-demercuration, the method which can be used to prepare the alcohol.
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Students have asked these similar questions
4-methyl-3-hexanol was prepared by reacting an alkene with either hydroboration-oxidation or oxymercuration-reduction.
Draw the structure of the alkene that was used to prepare the alcohol in highest yield.
You do not have to consider stereochemistry.
• Indicate the method of preparation by drawing either BH; (for
hydroboration-oxidation), or Hg (for oxymercuration-reduction), in a separate sketcher.
If there is more than one alkene that can be used for a given method, draw all of them.
If either hydroboration-oxidation or oxymercuration-reduction can be used, just give the structures for one method.
• Separate structures with + signs from the drop-down menu.
Select the reagent that you would use to convert an alkene to a Markovnikov (more
substituted) alcohol without possibility of carbocation rearrangement.
o H2SO4, H2O
OBH3-THF, then H2O2, H2O, NaOH
Hg(OAc)2, H2O, then NaBH4
o OsO4, TBHP, H2O
МЕСНANISMS
1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed
opening of the epoxide ring to form two different products.
> Using ethanol as the solvent and an appropriate acid, show the steps in the acid
catalyzed mechanism, writing structures for all products of the steps. Circle the major
product(s).
> Using ethanol as the solvent and an appropriate base, show the steps in the base-
catalyzed mechanism, writing structures for all products of the steps. Circle the major
product(s).
1,2-epoxy-1-methylcyclopentane
CH3
Chapter 8 Solutions
Organic Chemistry
Ch. 8.1 - Prob. 1PCh. 8.1 - How many alkene products, including E,Z isomers,...Ch. 8.2 - Prob. 3PCh. 8.2 - Addition of HCl to 1, 2-dimethylcyclohexene yields...Ch. 8.3 - Prob. 5PCh. 8.3 - Prob. 6PCh. 8.4 - Prob. 7PCh. 8.4 - From what alkenes might the following alcohols...Ch. 8.5 - Prob. 9PCh. 8.5 - What alkenes might be used to prepare the...
Ch. 8.5 - Tho following cycloalkene gives a mixture of two...Ch. 8.6 - Prob. 12PCh. 8.7 - Prob. 13PCh. 8.7 - Starting with an alkene, how would you prepare...Ch. 8.8 - Prob. 15PCh. 8.8 - Prob. 16PCh. 8.9 - What products would you expect from the following...Ch. 8.10 - Prob. 18PCh. 8.10 - Prob. 19PCh. 8.13 - Prob. 20PCh. 8.13 - What products are formed from hydration of...Ch. 8.SE - Name the following alkenes, and predict the...Ch. 8.SE - Prob. 23VCCh. 8.SE - Prob. 24VCCh. 8.SE - Prob. 25VCCh. 8.SE - Prob. 26MPCh. 8.SE - Prob. 27MPCh. 8.SE - Draw the structures of the organoboranes formed...Ch. 8.SE - Prob. 29MPCh. 8.SE - Provide the mechanism and products for the...Ch. 8.SE - Propose a curved-arrow mechanism to show how ozone...Ch. 8.SE - Prob. 32MPCh. 8.SE - Prob. 33MPCh. 8.SE - Prob. 34MPCh. 8.SE - 10-Bromo- α -chamigrene, a compound isolated from...Ch. 8.SE - Isolated from marine algae, prelaureatin is...Ch. 8.SE - Dichlorocarbene can be generated by heating sodium...Ch. 8.SE - Reaction of cyclohexene with mercury(II) acetate...Ch. 8.SE - Use your general knowledge of alkene chemistry to...Ch. 8.SE - Prob. 40MPCh. 8.SE - Hydroboration of 2-methyl-2-pentene at 25°C,...Ch. 8.SE - Prob. 42APCh. 8.SE - Suggest structures for alkenes that give the...Ch. 8.SE - Prob. 44APCh. 8.SE - Prob. 45APCh. 8.SE - Prob. 46APCh. 8.SE - Prob. 47APCh. 8.SE - Predict the products of the following reactions....Ch. 8.SE - Prob. 49APCh. 8.SE - How would you carry out the following...Ch. 8.SE - Draw the structure of an alkene that yields only...Ch. 8.SE - Show the structures of alkenes that give the...Ch. 8.SE - Prob. 53APCh. 8.SE - Which of the following alcohols could not be made...Ch. 8.SE - Prob. 55APCh. 8.SE - Prob. 56APCh. 8.SE - Prob. 57APCh. 8.SE - Compound A has the formula C10HI6. On catalytic...Ch. 8.SE - Prob. 59APCh. 8.SE - Prob. 60APCh. 8.SE - Prob. 61APCh. 8.SE - Draw the structure of a hydrocarbon that absorbs 2...Ch. 8.SE - Prob. 63APCh. 8.SE - The sex attractant of the common housefly is a...Ch. 8.SE - Prob. 65APCh. 8.SE - Prob. 66APCh. 8.SE - α-Terpinene, C10H16, is a pleasant-smelling...Ch. 8.SE - Prob. 68APCh. 8.SE - Prob. 69APCh. 8.SE - Prob. 70APCh. 8.SE - Prob. 71APCh. 8.SE - Prob. 72AP
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