Concept explainers
a) Cyclopentanone
Interpretation:
How to prepare cyclopentanone from cyclopentanol is to be stated.
Concept introduction:
To state:
How to prepare cyclopentanone from cyclopentanol.
b) Cyclopentene
Interpretation:
How to prepare cyclopentene from cyclopentanol is to be stated.
Concept introduction:
Alcohols can be converted into
To state:
How to prepare cyclopentene from cyclopentanol.
c) 1-Methylcyclopentanol
Interpretation:
How to prepare1-methylcyclopentanol from cyclopentanol is to be stated.
Concept introduction:
A 20 alcohol is to be converted into a 30 alcohol. Oxidizing the alcohol to a ketone and treating the ketone with a Grignard reagent will lead to the formation of the 30 alcohol.
To state:
How to prepare 1-methylcyclopentanol from cyclopentanol is to be stated.
d) trans-2-Methylcyclopentanol
Interpretation:
How to prepare trans-2-Methylcyclopentanol from cyclopentanol is to be stated.
Concept introduction:
Alcohols when treated with acids undergo dehydration to yield an alkene. The alkenes can be hydrated either by oxymercuration-demercuration process following Markovnikov regiochemistry or by hydroboration-oxidation following anti-Markovnikov regiochemistry.
To state:
How to prepare trans-2-methylcyclopentanol from cyclopentanol.
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Chapter 17 Solutions
Organic Chemistry
- When 1-butanol is treated with conc. H2SO4 and heat .A product 'A' is formed from the reaction. Treatment of 'A' with HCl/H2O gives 'B'. Treatment of 'A' with cold KMnO4/OH- gives 'C' Treatment of 'A' with hot KMnO4 /OH- gives 'D' followed by acidification of the mixture to give 'E' 1. identify the compounds represented by A,B,C,D and E.arrow_forwardHydroboration of 2-methyl-2-pentene at 25°C, followed by oxidation with alkaline H2o2, yields 2-methyl-3-pentanol, but hydroboration at 160°C followed by oxidation yields 4-methyl-1-pentanol. Suggest a mechanism.arrow_forwardA. In the synthesis of 1-bromobutane, what is the inorganic by-product left in the reaction flask following the distillation? Why was the bromoalkane the bottom layer in the separatory funnel? B. Predict the product when 1-methylcyclohexanol reacts with H2SO4 and KBr. Show the mechanism.arrow_forward
- The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.arrow_forwardTreatment of 1-aminoadamantane, C10H17N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. Propose a structural formula for compound A.arrow_forwardA step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.arrow_forward
- Following is the structural formula of Surfynol, a defoaming surfactant. Describe the synthesis of this compound from acetylene and a ketone. How many stereoisomers are possible for Surfynol?arrow_forwardWhen 2-methyl-2, 5-pentanediol is treated with sulfuric acid, dehydration occurs and 2, 2-dimethyltetrahydrofuran is formed. Suggest a mechanism for this reaction. Which of the two oxygen atoms is most likely to be eliminated, and why?arrow_forwardPropose a structural formula for compound A, C5H13N, given its IR and calculated 1H-NMR spectra.arrow_forward
- Propose a mechanism for the acid-catalyzed hydration of methylidenecyclohexane to give 1-methylcyclohexanol. Which step in your mechanism is rate-determining?arrow_forward2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH. (i) Draw the structural formula of compounds W, X and Yarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning